Product Name

  • Name

    Triethyl phosphonoacetate

  • EINECS 212-757-6
  • CAS No. 867-13-0
  • Article Data101
  • CAS DataBase
  • Density 1.13 g/cm3
  • Solubility Slightly miscible with water.
  • Melting Point -24 °C
  • Formula C8H17O5P
  • Boiling Point 287.4 °C at 760 mmHg
  • Molecular Weight 224.194
  • Flash Point 141.6 °C
  • Transport Information UN 3082 9/PG 3
  • Appearance colorless to light yellow liquid
  • Safety 61-37/39-26-36
  • Risk Codes 51/53-36/37/38
  • Molecular Structure Molecular Structure of 867-13-0 (Triethyl phosphonoacetate)
  • Hazard Symbols DangerousN,IrritantXi,HarmfulXn
  • Synonyms Diethyl phosphonoacetic acid, ethyl ester;Phosphonoacetic acid, triethyl ester;Acetic acid, phosphono-, triethyl ester;Acetic acid, (diethylphosphono)-, ethyl ester;Ethyl (diethylphosphono)acetate;Acetic acid, diethylphosphono-, ethyl ester;ethyl 2-diethoxyphosphorylacetate;Diethyl ethoxycarbonylmethanephosphonate;TL 465;Acetic acid, (diethoxyphosphinyl)-, ethyl ester;Diethyl carboethoxymethylphosphonate;(Ethoxycarbonylmethyl)diethoxyphospshine oxide;Diethyl carbethoxymethylphosphonate;Ethyl (diethoxyphosphoryl)acetate;
  • PSA 71.64000
  • LogP 1.81560

Synthetic route

ethyl bromoacetate
105-36-2

ethyl bromoacetate

triethyl phosphite
122-52-1

triethyl phosphite

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
at 60 - 80℃; for 0.5h; Arbusov reaction;100%
at 150℃; for 3h;99%
for 0.0333333h; Michaelis-Arbuzov reaction; microwave irradiation;98%
chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

triethyl phosphite
122-52-1

triethyl phosphite

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
In toluene at 170℃; under 7500.75 Torr; for 0.333333h; Pressure; Temperature; Arbuzov Reaction; Large scale;95%
at 120 - 165℃; for 2h;93%
for 2h; Inert atmosphere; Reflux;63%
chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
With triethyl phosphite89.3%
triethyl phosphate
78-40-0

triethyl phosphate

ethyl bromoacetate
105-36-2

ethyl bromoacetate

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
at 140℃; for 3h;88%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
With copper acetylacetonate In benzene Product distribution; Heating; other catalysts, other diazo compounds, other hydrophosphoryl compounds;83%
copper acetylacetonate In benzene for 1h; Heating;83%
With copper acetylacetonate In benzene Heating;83%
With trifluorormethanesulfonic acid In benzene Heating;2%
chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate; 18-crown-6 ether at 80℃; for 6h;77%
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane at 0 - 5℃; for 0.333333h;55%
With potassium carbonate In ethanol at 78℃; for 2h; Substitution; Michaelis-Becker reaction;33%
methyl vinyl ketone
78-94-4

methyl vinyl ketone

diethyl 1-iodo-1-carbethoxy-methylphosphonate
66700-63-8

diethyl 1-iodo-1-carbethoxy-methylphosphonate

A

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

B

2-(Diethoxy-phosphoryl)-5-oxo-hexanoic acid ethyl ester

2-(Diethoxy-phosphoryl)-5-oxo-hexanoic acid ethyl ester

Conditions
ConditionsYield
With triethyl borane; tri-n-butyl-tin hydride In hexane; toluene at -78℃; for 6h; Yields of byproduct given;A n/a
B 77%
...Expand
Diethyl methylphosphonate
683-08-9

Diethyl methylphosphonate

XC(O)OC2H5

XC(O)OC2H5

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
With n-butyllithium; lithium diisopropyl amide In tetrahydrofuran; hexane at -60℃;74%
2-(5-methyl-2-phenyl-4-oxazolyl)methyl-5-benzofurancarboxaldehyde
132646-34-5

2-(5-methyl-2-phenyl-4-oxazolyl)methyl-5-benzofurancarboxaldehyde

A

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

B

ethyl (E)-3-[2-(5-methyl-2-phenyl-4-oxazolylmethyl)benzofuran-5-yl]acrylate
159017-57-9

ethyl (E)-3-[2-(5-methyl-2-phenyl-4-oxazolylmethyl)benzofuran-5-yl]acrylate

Conditions
ConditionsYield
A n/a
B 74%
Methyl diethylphosphonoacetate
1067-74-9

Methyl diethylphosphonoacetate

(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-oxo-1H-pyrrolo-<2,3-d>carbazole-6-carboxylate
219650-29-0

(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-oxo-1H-pyrrolo-<2,3-d>carbazole-6-carboxylate

A

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

B

(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E)-<(methoxycarbonyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates
219650-31-4

(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E)-<(methoxycarbonyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates

C

(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(Z)-<(methoxycarbonyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates
219650-30-3

(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(Z)-<(methoxycarbonyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates

Conditions
ConditionsYield
With potassium hexamethyldisilazane In tetrahydrofuran for 0.5h; Ambient temperature; Yield given;A n/a
B 64%
C n/a
...Expand
Diethyl phosphonate
762-04-9, 123-22-8

Diethyl phosphonate

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
With sodium In diethyl ether60%
(E)-4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]cinnamaldehyde
159017-37-5

(E)-4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]cinnamaldehyde

A

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

B

ethyl (E)-5-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]-2,4-pentadienoate
1026936-75-3

ethyl (E)-5-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]-2,4-pentadienoate

Conditions
ConditionsYield
A n/a
B 56%
vinyl acetate
108-05-4

vinyl acetate

diethyl 1-iodo-1-carbethoxy-methylphosphonate
66700-63-8

diethyl 1-iodo-1-carbethoxy-methylphosphonate

A

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

B

4-Acetoxy-2-(diethoxy-phosphoryl)-butyric acid ethyl ester

4-Acetoxy-2-(diethoxy-phosphoryl)-butyric acid ethyl ester

Conditions
ConditionsYield
With triethyl borane; tri-n-butyl-tin hydride In hexane; toluene at -78℃; for 6h; Yields of byproduct given;A n/a
B 38%
...Expand
triethyl 2-chloro-2-phosphonoacetate
7071-12-7

triethyl 2-chloro-2-phosphonoacetate

A

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

B

(E)-ethyl 2-chloro-3-(4-methoxyphenyl)propenoate
66051-39-6

(E)-ethyl 2-chloro-3-(4-methoxyphenyl)propenoate

C

(E)-methoxyphenyl-3 chloro-2 propenoate d'ethyle
66051-40-9

(E)-methoxyphenyl-3 chloro-2 propenoate d'ethyle

Conditions
ConditionsYield
With tetramethylammonium tetrafluoroborate; 4-methoxy-benzaldehyde In N,N-dimethyl-formamide Ambient temperature; controlled potential electrolysis; cathode: Hg; electrode ref.: AgI/Ag; Yields of byproduct given;A 22%
B n/a
C n/a
...Expand
triethyl 2-chloro-2-phosphonoacetate
7071-12-7

triethyl 2-chloro-2-phosphonoacetate

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

A

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

B

(E)-ethyl 2-chloro-3-(4-methoxyphenyl)propenoate
66051-39-6

(E)-ethyl 2-chloro-3-(4-methoxyphenyl)propenoate

C

(E)-methoxyphenyl-3 chloro-2 propenoate d'ethyle
66051-40-9

(E)-methoxyphenyl-3 chloro-2 propenoate d'ethyle

Conditions
ConditionsYield
With tetramethylammonium tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; controlled potential electrolysis; cathode: Hg; electrode ref.: AgI/Ag; Yield given;A 22%
B n/a
C n/a
...Expand
triethyl 2-chloro-2-phosphonoacetate
7071-12-7

triethyl 2-chloro-2-phosphonoacetate

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

A

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

B

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

C

(Z)-ethyl 3-(4-methoxyphenyl)acrylate
51507-22-3

(Z)-ethyl 3-(4-methoxyphenyl)acrylate

Conditions
ConditionsYield
With tetramethylammonium tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; controlled potential electrolysis; cathode: Hg; electrode ref.: AgI/Ag; Yield given;A 14%
B n/a
C n/a
...Expand
diethyl ether
60-29-7

diethyl ether

sodium diethyl phosphite
2303-76-6, 118080-94-7

sodium diethyl phosphite

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

...Expand
sodium diethyl phosphite
2303-76-6, 118080-94-7

sodium diethyl phosphite

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
With hexane
With ligroine
With ethanol
sodium diethyl phosphite
2303-76-6, 118080-94-7

sodium diethyl phosphite

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

benzene
71-43-2

benzene

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

...Expand
sodium diethyl phosphite
2303-76-6, 118080-94-7

sodium diethyl phosphite

ethyl bromoacetate
105-36-2

ethyl bromoacetate

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
With benzene
ethanol
64-17-5

ethanol

dichlorophosphoryl-acetyl chloride
34164-06-2

dichlorophosphoryl-acetyl chloride

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
With pyridine In diethyl ether
diethyl ester of 2,2-diethoxyethenephosphonic acid
34159-39-2

diethyl ester of 2,2-diethoxyethenephosphonic acid

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
With sulfuric acid; water
2-Diethoxyphosphoryl-3-dimethylaminoacrylsaeure-ethylester
74119-48-5

2-Diethoxyphosphoryl-3-dimethylaminoacrylsaeure-ethylester

A

benzoimidazole
51-17-2

benzoimidazole

B

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
With 1,2-diamino-benzene In ethanol Heating;
diethyl phosphorylchloridite
589-57-1

diethyl phosphorylchloridite

ethyl acetate
141-78-6

ethyl acetate

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
Yield given. Multistep reaction. Further byproducts given;
Diazoethan
1117-96-0

Diazoethan

carbon dioxide
124-38-9

carbon dioxide

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

methyl iodide
74-88-4

methyl iodide

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
In diethyl ether at 0℃; for 0.5h;
...Expand
2-Diethoxyphosphoryl-3-dimethylaminoacrylsaeure-ethylester
74119-48-5

2-Diethoxyphosphoryl-3-dimethylaminoacrylsaeure-ethylester

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

benzoimidazole
51-17-2

benzoimidazole

B

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
In ethanol Heating;
...Expand
Diethyl methylphosphonate
683-08-9

Diethyl methylphosphonate

Diethyl carbonate
105-58-8

Diethyl carbonate

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
With n-butyllithium; diisopropylamine 1.) hexane, THF, -78 deg C, 5 min, 2.) THF, -78 deg C --> 0 deg C; Yield given. Multistep reaction;
With n-butyllithium 1.) THF, hexane, -55 deg C, 20 min, 2.) THF, hexane, -55 deg C, 30 min; Yield given. Multistep reaction;
ethyl bromoacetate
105-36-2

ethyl bromoacetate

triethyl phosphite
122-52-1

triethyl phosphite

A

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

B

phosphoric acid 1-ethoxy-vinyl ester diethyl ester
63720-98-9

phosphoric acid 1-ethoxy-vinyl ester diethyl ester

Conditions
ConditionsYield
In benzene for 8h; Heating;
In benzene for 8h; Heating;
...Expand
ethyl 2,2-dichloro-2-diethoxyphosphorylacetate
5823-12-1

ethyl 2,2-dichloro-2-diethoxyphosphorylacetate

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 7 percent / p-methoxybenzaldehyde, Me4NBF4 / dimethylformamide / Ambient temperature; controlled potential electrolysis; cathode: Hg; electrode ref.: AgI/Ag
2: 22 percent / Me4NBF4, p-methoxybenzaldehyde / dimethylformamide / Ambient temperature; controlled potential electrolysis; cathode: Hg; electrode ref.: AgI/Ag
View Scheme
Multi-step reaction with 2 steps
1: 7 percent / p-methoxybenzaldehyde, Me4NBF4 / dimethylformamide / Ambient temperature; controlled potential electrolysis; cathode: Hg; electrode ref.: AgI/Ag
2: 22 percent / Me4NBF4 / dimethylformamide / Ambient temperature; controlled potential electrolysis; cathode: Hg; electrode ref.: AgI/Ag
View Scheme
formaldehyd
50-00-0

formaldehyd

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

ethyl 2-diethoxyphosphinoylacrylate
20345-61-3

ethyl 2-diethoxyphosphinoylacrylate

Conditions
ConditionsYield
Stage #1: formaldehyd; diethoxyphosphoryl-acetic acid ethyl ester With piperidine In methanol at 80℃; for 36h;
Stage #2: With toluene-4-sulfonic acid In toluene for 16h; Dean-Stark; Reflux;		100%
Stage #1: formaldehyd With piperidine In methanol for 0.5h; Heating;
Stage #2: diethoxyphosphoryl-acetic acid ethyl ester In methanol for 70h; Heating;		73%
piperidine In methanol Heating;60%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

cyclohexanone
108-94-1

cyclohexanone

ethyl cyclohexylideneacetate
1552-92-7

ethyl cyclohexylideneacetate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil for 1h;
Stage #2: cyclohexanone In tetrahydrofuran; mineral oil for 18h;		100%
With sodium hydride In tetrahydrofuran for 8h;98%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With 15-crown-5; sodium hydride In tetrahydrofuran; mineral oil at 0℃;
Stage #2: cyclohexanone In tetrahydrofuran; mineral oil at -40 - 20℃;		97%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

heptanal
111-71-7

heptanal

ethyl 2-nonenoate
17463-01-3

ethyl 2-nonenoate

Conditions
ConditionsYield
With triethylamine; magnesium bromide In tetrahydrofuran at 25℃; for 12h;100%
(i) NaH, Et2O, (ii) /BRN= 1560236/; Multistep reaction;
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

4-heptanone
123-19-3

4-heptanone

ethyl 3-propylhex-2-enoate
10297-63-9

ethyl 3-propylhex-2-enoate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 20℃;
Stage #2: 4-heptanone at 20℃; for 24h; Reflux;		100%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Schlenk technique; Inert atmosphere;
Stage #2: 4-heptanone In tetrahydrofuran; mineral oil at 20℃; Schlenk technique; Inert atmosphere;		88%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester; 4-heptanone With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.333333h; Inert atmosphere; Schlenk technique;
Stage #2: In tetrahydrofuran; mineral oil for 20h; Reflux;		86%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

diethylphosphonoacetic acid
3095-95-2

diethylphosphonoacetic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 20℃;100%
With water; sodium hydroxide In ethanol at 20℃; Inert atmosphere;97%
With hydrogenchloride; potassium hydroxide 1.) aq. EtOH, 20 h;95%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

pivalaldehyde
630-19-3

pivalaldehyde

3-tert-butyl-acrylic acid ethyl ester
87995-20-8

3-tert-butyl-acrylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran Cooling with ice;
Stage #2: pivalaldehyde In tetrahydrofuran at 20℃; for 48h;
Stage #3: With ammonium chloride In tetrahydrofuran; water		100%
(i) NaH, Et2O, (ii) /BRN= 506060/; Multistep reaction;
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #2: pivalaldehyde In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
With sodium tert-pentoxide at 0 - 20℃; for 1h; Horner-Wadsworth-Emmons Olefination; Green chemistry;
With sodium hydride In tetrahydrofuran at 0℃; Inert atmosphere;
furfural
98-01-1

furfural

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

ethyl (E)-3-(2-furyl)prop-2-enoate
623-20-1

ethyl (E)-3-(2-furyl)prop-2-enoate

Conditions
ConditionsYield
With potassium carbonate In neat (no solvent) Mechanism; var. other bases, effect of water;100%
With water; barium dihydroxide In 1,4-dioxane at 70℃; for 0.416667h;100%
With water; barium dihydroxide In 1,4-dioxane at 70℃; for 0.416667h; Product distribution; other catalyst, other solvents, influence of water;100%
3-thiophene carboxaldehyde
498-62-4

3-thiophene carboxaldehyde

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

(E)-3-thiophen-3-yl-acrylic acid ethyl ester
50266-60-9

(E)-3-thiophen-3-yl-acrylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h;
Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran; mineral oil at 20℃; for 1h;		100%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h;
Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran; mineral oil at 0 - 20℃; for 3.25h;		100%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With potassium tert-butylate In tetrahydrofuran at 20℃;
Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran at 90℃; for 0.5h;		90%
Tetrahydro-4H-pyran-4-one
29943-42-8

Tetrahydro-4H-pyran-4-one

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

ethyl tetrahydro-4H-pyran-4-ylideneacetate
130312-00-4

ethyl tetrahydro-4H-pyran-4-ylideneacetate

Conditions
ConditionsYield
With sodium hydride In mineral oil; benzene at 0 - 20℃; for 2.33333h; Inert atmosphere;100%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Schlenk technique; Inert atmosphere;
Stage #2: Tetrahydro-4H-pyran-4-one In tetrahydrofuran; mineral oil at 20℃; Schlenk technique; Inert atmosphere;		100%
With potassium carbonate In N,N-dimethyl-formamide at 80℃;96%
cyclohexanedione monoethylene ketal
4746-97-8

cyclohexanedione monoethylene ketal

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

ethyl 1,4-dioxaspiro[4,5]dec-8-ylideneacetate
51656-91-8

ethyl 1,4-dioxaspiro[4,5]dec-8-ylideneacetate

Conditions
ConditionsYield
With sodium hydride In 1,2-dimethoxyethane for 11.5h; Ambient temperature;100%
With sodium hydride In tetrahydrofuran at 0℃; for 0.666667h; Horner-Wadsworth-Emmons reaction;100%
Stage #1: cyclohexanedione monoethylene ketal With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h;
Stage #2: diethoxyphosphoryl-acetic acid ethyl ester In tetrahydrofuran; mineral oil at -20 - 20℃; for 3h;		100%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

ethyl P,P-bis(trimethylsilyl) phosphonoacetate
65868-40-8

ethyl P,P-bis(trimethylsilyl) phosphonoacetate

Conditions
ConditionsYield
at 100℃; for 168h; Inert atmosphere;100%
With potassium iodide In acetonitrile at 25 - 35℃; for 0.5h;
In chlorobenzene at 140℃; for 18h;
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Octanal
124-13-0

Octanal

ethyl (E)-2-decenate
7367-88-6

ethyl (E)-2-decenate

Conditions
ConditionsYield
With n-butyllithium In 1,2-dimethoxyethane; hexane 1.) 0 deg C, 10 min, 2.) 30 min;100%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In diethyl ether at 0℃; for 0.0833333h;
Stage #2: Octanal In diethyl ether for 0.25h;		96%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In diethyl ether; mineral oil at 0℃;
Stage #2: Octanal In diethyl ether; mineral oil at 0℃;		96%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

(E)-4,4-Dimethyl-7-(2-oxo-cyclohex-3-enyl)-hept-2-enal

(E)-4,4-Dimethyl-7-(2-oxo-cyclohex-3-enyl)-hept-2-enal

6-(6-ethoxycarbonyl-4,4-dimethylhex-5-enyl)cyclohex-2-enone
91200-48-5

6-(6-ethoxycarbonyl-4,4-dimethylhex-5-enyl)cyclohex-2-enone

Conditions
ConditionsYield
With sodium hydride In 1,2-dimethoxyethane for 1h; Ambient temperature;100%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

(3S,10S,13S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta-[a]phenanthren-17-one
57711-44-1

(3S,10S,13S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta-[a]phenanthren-17-one

(E)-ethyl 3β-(tert-butyldimethylsiloxy)-5α-pregn-17-(20)-en-21-oate
115019-45-9

(E)-ethyl 3β-(tert-butyldimethylsiloxy)-5α-pregn-17-(20)-en-21-oate

Conditions
ConditionsYield
With sodium ethanolate In tetrahydrofuran; ethanol at 85℃; for 15h;100%
With sodium ethanolate In tetrahydrofuran; ethanol for 10h; Heating;98.6%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

(E)-4-<(E)-1-methyl-3-(2,6,6-trimethyl-1-cyclohexenyl)-2-propenylidene>-2-cyclohexen-1-one
123718-34-3

(E)-4-<(E)-1-methyl-3-(2,6,6-trimethyl-1-cyclohexenyl)-2-propenylidene>-2-cyclohexen-1-one

ethyl (13E/Z)-10,20-methanoretinoate

ethyl (13E/Z)-10,20-methanoretinoate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 2.5h; Ambient temperature;100%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

7-(4-tert-butylbenzyl)-2-(4-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazole-3-carboxaldehyde
144148-22-1

7-(4-tert-butylbenzyl)-2-(4-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazole-3-carboxaldehyde

ethyl (E)-3-<7-(4-tert-butylbenzyl)-2-(4-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl>-2-propenoate
144148-78-7

ethyl (E)-3-<7-(4-tert-butylbenzyl)-2-(4-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl>-2-propenoate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran Ambient temperature;100%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

(5-Oxo-1-trityloxymethyl-pentyl)-carbamic acid methyl ester

(5-Oxo-1-trityloxymethyl-pentyl)-carbamic acid methyl ester

rac-(E)-ethyl 7-(methoxycarbonyl)amino-8-(trityloxy)-2-octenoate
157330-99-9

rac-(E)-ethyl 7-(methoxycarbonyl)amino-8-(trityloxy)-2-octenoate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 0.5h; Ambient temperature;100%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

(E)-ethyl 3-(3-nitrophenyl)acrylate
621-19-2

(E)-ethyl 3-(3-nitrophenyl)acrylate

Conditions
ConditionsYield
With water; barium dihydroxide In 1,4-dioxane at 70℃; for 0.416667h;100%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester; 3-nitro-benzaldehyde With lithium chloride In acetonitrile at 0℃; for 0.0833333h; Horner-Wadsworth-Emmons reaction;
Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃;		96%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h;
Stage #2: 3-nitro-benzaldehyde In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h;		93%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

ethyl (E)-3-(3,4,5-trimethoxyphenyl)acrylate
1878-29-1, 30273-65-5, 31892-98-5

ethyl (E)-3-(3,4,5-trimethoxyphenyl)acrylate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With lithium chloride In tetrahydrofuran at 20℃; for 0.25h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;
Stage #2: 3,4,5-trimethoxy-benzaldehyde With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran Horner-Wadsworth-Emmons Olefination; Inert atmosphere;		100%
With potassium carbonate In water at 70℃; for 4h;90%
With potassium carbonate In water at 70℃; for 4h; Wittig Olefination; stereoselective reaction;90%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

benzaldehyde
100-52-7

benzaldehyde

ethyl cinnamate
4192-77-2

ethyl cinnamate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 1h;100%
With potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 2h; Horner-Wadsworth-Emmons reaction; neat (no solvent); optical yield given as %de; stereoselective reaction;100%
With n-butyllithium In tetrahydrofuran; hexane 1.) 0 deg C, 10 min, 2.) 30 min;99%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

ethyl (E)-3-(3-chlorophenyl)prop-2-enoate
2373-88-8, 118315-76-7, 62174-98-5

ethyl (E)-3-(3-chlorophenyl)prop-2-enoate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 23℃; for 1h;
Stage #2: m-Chlorobenzaldehyde In tetrahydrofuran for 1h;		100%
With sodium hydride In N,N-dimethyl-formamide at -60℃; Horner-Wadsworth-Emmons Olefination;95%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 30℃; for 4h; Glovebox;84%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

ethyl (E)-3-(3-methoxyphenyl)acrylate
33877-04-2, 24393-55-3

ethyl (E)-3-(3-methoxyphenyl)acrylate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With lithium chloride In tetrahydrofuran at 20℃; for 0.25h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;
Stage #2: 3-methoxy-benzaldehyde With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran Horner-Wadsworth-Emmons Olefination; Inert atmosphere;		100%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h;100%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 30℃; for 4h; Glovebox;98%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

isovaleraldehyde
590-86-3

isovaleraldehyde

ethyl (E)-5-methylhex-2-enoate
34993-63-0

ethyl (E)-5-methylhex-2-enoate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In 1,2-dimethoxyethane at 0℃; for 0.416667h;
Stage #2: isovaleraldehyde In 1,2-dimethoxyethane for 16h; Horner-Emmons homologation; Heating;		100%
With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 6h; Wadsworth-Honer-Emmons olefination;95%
With sodium hydride In tetrahydrofuran90%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

2,6-dimethylbenzaldehyde
1123-56-4

2,6-dimethylbenzaldehyde

ethyl (E)-3-(2,6-dimethylphenyl)-2-propenoate
527759-23-5

ethyl (E)-3-(2,6-dimethylphenyl)-2-propenoate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: 2,6-dimethylbenzaldehyde In tetrahydrofuran at 20℃; for 6h; Horner-Wadsworth-Emmons reaction;		100%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 30℃; for 4h; Glovebox;97%
With potassium tert-butylate Horner-Wadsworth-Emmons olefination;89%
With potassium tert-butylate In tetrahydrofuran Ambient temperature;
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

isobutyraldehyde
78-84-2

isobutyraldehyde

(E)-2-(Diethoxy-phosphoryl)-4-methyl-pent-2-enoic acid ethyl ester
173724-80-6

(E)-2-(Diethoxy-phosphoryl)-4-methyl-pent-2-enoic acid ethyl ester

Conditions
ConditionsYield
With piperidine; acetic acid In benzene for 48h; Heating;100%
With piperidine; acetic acid for 62h; Condensation; Knoevenagel condensation;80%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With triethylamine; titanium tetrachloride In dichloromethane at 0 - 5℃;
Stage #2: isobutyraldehyde In dichloromethane at 0 - 5℃; Horner-Wadsworth-Emmos reaction;
3,4-dibenzyloxybenzaldehyde
5447-02-9

3,4-dibenzyloxybenzaldehyde

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

3-(3,4-bis-benzyloxy-phenyl)-acrylic acid ethyl ester
203571-40-8

3-(3,4-bis-benzyloxy-phenyl)-acrylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran
Stage #2: 3,4-dibenzyloxybenzaldehyde In tetrahydrofuran for 0.166667h; Further stages.;		100%
With sodium hydride In 1,2-dimethoxyethane for 0.333333h;99.5%
With sodium In ethanol Ambient temperature;76%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

(S)-3-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-thiazol-4-yl]-butyraldehyde
185996-42-3

(S)-3-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-thiazol-4-yl]-butyraldehyde

(E)-(S)-5-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-thiazol-4-yl]-hex-2-enoic acid ethyl ester
185996-43-4

(E)-(S)-5-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-thiazol-4-yl]-hex-2-enoic acid ethyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile for 0.25h; Ambient temperature;100%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

(1R,5R,6R)-2-[6-(tert-butyldimethylsilanyloxymethyl)-5-isopropyl-2-methylcyclohex-2-enyl]acetaldehyde
198336-00-4

(1R,5R,6R)-2-[6-(tert-butyldimethylsilanyloxymethyl)-5-isopropyl-2-methylcyclohex-2-enyl]acetaldehyde

(E)-4-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-but-2-enoic acid ethyl ester
198336-01-5

(E)-4-[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-isopropyl-2-methyl-cyclohex-2-enyl]-but-2-enoic acid ethyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0 - 25℃;100%
With sodium hydride 1.) THF, 25 deg C, 30 min, 2.) THF, from 0 to 25 deg C, 5 h; Yield given. Multistep reaction;
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

(1,1-dimethyl-3-oxo-propyl)-carbamic acid tert-butyl ester
181646-38-8

(1,1-dimethyl-3-oxo-propyl)-carbamic acid tert-butyl ester

ethyl (2E)-5-(tert-butoxycarbonylamino)-5-methylhex-2-enoate
181646-40-2

ethyl (2E)-5-(tert-butoxycarbonylamino)-5-methylhex-2-enoate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With potassium tert-butylate In toluene at 60℃; for 0.5h; Wittig-Horner reaction;
Stage #2: (1,1-dimethyl-3-oxo-propyl)-carbamic acid tert-butyl ester In toluene at 60℃; for 0.166667h; Wittig-Horner reaction;		100%
With potassium tert-butylate 1.) THF, RT, 40 min, 2.) THF, RT, 75 min; Yield given. Multistep reaction;
With potassium tert-butylate; sodium hydrogencarbonate In tetrahydrofuran; n-heptane

Triethyl Phosphonoacetate Specification

The IUPAC name of Triethyl Phosphonoacetate is ethyl 2-diethoxyphosphorylacetate. With the CAS registry number 867-13-0, it is also named as (Ethoxycarbonylmethyl)diethoxyphospshine oxide; Acetic acid, (diethylphosphono)-, ethyl ester. The product's categories are Wittig reagents, Horner-Emmons reaction, synthetic organic chemistry and Wittig & Horner-Emmons reaction. Furthermore, it is colorless to light yellow liquid.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.92; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.92; (4)ACD/LogD (pH 7.4): 0.92; (5)ACD/BCF (pH 5.5): 2.93; (6)ACD/BCF (pH 7.4): 2.93; (7)ACD/KOC (pH 5.5): 75.15; (8)#H bond acceptors: 5; (9)#H bond donors: 0; (10)#Freely Rotating Bonds: 8; (11)Index of Refraction: 1.423; (12)Molar Refractivity: 51.25 cm3; (13)Molar Volume: 200.9 cm3; (14)Polarizability: 20.31×10-24 cm3; (15)Surface Tension: 34.3 dyne/cm; (16)Enthalpy of Vaporization: 52.66 kJ/mol; (17)Vapour Pressure: 0.00248 mmHg at 25°C; (18)Rotatable Bond Count: 8; (19)Exact Mass: 224.08136; (20)MonoIsotopic Mass: 224.08136; (21)Topological Polar Surface Area: 61.8; (22)Heavy Atom Count: 14.

Preparation of Triethyl Phosphonoacetate: It can be obtained by bromoacetic acid ethyl ester and phosphorous acid triethyl ester under arbusov reaction at 60-80 °C. The reaction time is 30 min. The yield is 100%. 

Uses of Triethyl Phosphonoacetate: It is an important Horner-Wittig reagent and intermediate of preparation of Vitamin compounds, drugs, insect pheromones and other natural compounds. For example: It can react with cyclohexanone to get cyclohexyliden-acetic acid ethyl ester. This reaction which is Wittig-Wadsworth-Emmons reaction needs reagent NaH and solvent tetrahydrofuran at temperature of 20 °C. The reaction time is 8 hours. The yield is 94%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. And it is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment, so people should avoid releasing to the environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing and suitable gloves and eye/face protection.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=P(OCC)(OCC)CC(=O)OCC;
2. InChI:InChI=1/C8H17O5P/c1-4-11-8(9)7-14(10,12-5-2)13-6-3/h4-7H2,1-3H3.

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LCLo inhalation 1180mg/m3/10M (1180mg/m3)   National Defense Research Committee, Office of Scientific Research and Development, Progress Report.Vol. NDCrc-132, Pg. NOV1942,
rat LD oral > 500mg/kg (500mg/kg)   National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 15, 1953.

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