Product Name

  • Name

    Ethyl diethoxyphosphinylformate

  • EINECS 216-016-8
  • CAS No. 1474-78-8
  • Article Data13
  • CAS DataBase
  • Density 1.11
  • Solubility
  • Melting Point
  • Formula C7H15 O5 P
  • Boiling Point 135 ºC (12 mmHg)
  • Molecular Weight 210.167
  • Flash Point >110 ºC
  • Transport Information
  • Appearance Clear, colorless liquid.
  • Safety S24/25
  • Risk Codes 36/37/38-43
  • Molecular Structure Molecular Structure of 1474-78-8 (Ethyl diethoxyphosphinylformate)
  • Hazard Symbols Xi
  • Synonyms Formicacid, phosphono-, triethyl ester (7CI,8CI); Phosphinecarboxylic acid,diethoxy-, ethyl ester, oxide (9CI); Diethyl (ethoxycarbonyl)phosphonate;Diethyl carbethoxyphosphonate; Ethyl diethylphosphonoformate; NSC 108684;Triethyl carboxyphosphonate; Triethyl phosphonoformate
  • PSA 71.64000
  • LogP 2.40900

Synthetic route

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

triethyl phosphite
122-52-1

triethyl phosphite

triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

Conditions
ConditionsYield
91%
dimethoxymethyl phosphonic acid dimethyl ester
30410-95-8

dimethoxymethyl phosphonic acid dimethyl ester

triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

Conditions
ConditionsYield
With N-Bromosuccinimide In benzene for 1h; Heating; argon atmosphere;80%
diethyl(diethoxymethyl)phosphonate
17997-33-0

diethyl(diethoxymethyl)phosphonate

triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

Conditions
ConditionsYield
With N-Bromosuccinimide In benzene for 1h; Heating;80%
With di-tert-butyl peroxide In chlorobenzene at 120℃; Rate constant; Mechanism; Product distribution; various solvents, various temperature;
sodium diethyl phosphite
2303-76-6, 118080-94-7

sodium diethyl phosphite

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

Conditions
ConditionsYield
With diethyl ether
With Petroleum ether
ethanol
64-17-5

ethanol

N,N'-Bis-(O,O-diaethyl-phosphonocarbonyl)-sulfonyldiamid
20537-54-6

N,N'-Bis-(O,O-diaethyl-phosphonocarbonyl)-sulfonyldiamid

triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

Conditions
ConditionsYield
for 13h; Heating;
oxophosphonoacetic acid triethyl ester
16540-25-3

oxophosphonoacetic acid triethyl ester

triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

Conditions
ConditionsYield
at 150℃;
Tris-aethoxycarbonyl-phosphorotrithioit
998-02-7

Tris-aethoxycarbonyl-phosphorotrithioit

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

tris(ethoxythiocarbonyl) phosphorotrithioite
4373-18-6

tris(ethoxythiocarbonyl) phosphorotrithioite

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

diethyl <(ethylenedioxy)methyl>phosphonate
34909-25-6

diethyl <(ethylenedioxy)methyl>phosphonate

triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

Conditions
ConditionsYield
With di-tert-butyl peroxide In chlorobenzene at 120℃; Rate constant; Mechanism; Product distribution; various solvents, various temperature;
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

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 lithium hydroxide In tetrahydrofuran at 20℃; Horner-Wadsworth-Emmons Olefination;97%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

4-(2-nitrophenoxy)benzaldehyde
172932-06-8

4-(2-nitrophenoxy)benzaldehyde

(E)-ethyl 3-[4-(2-nitrophenoxy)phenyl]acrylate

(E)-ethyl 3-[4-(2-nitrophenoxy)phenyl]acrylate

Conditions
ConditionsYield
Stage #1: triethyl phosphonoformate With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile at 20℃; for 1h; Horner-Wadsworth-Emmons Olefination;
Stage #2: 4-(2-nitrophenoxy)benzaldehyde In acetonitrile at 20℃; for 18h; Horner-Wadsworth-Emmons Olefination;		94%
tert-butyl N-{4-[2-(4-formylphenoxy)ethyl]phenyl}carbamate
218139-11-8

tert-butyl N-{4-[2-(4-formylphenoxy)ethyl]phenyl}carbamate

triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

(E)-ethyl 3-{4-[2-(4-{[(tert-butoxy)carbonyl]amino}phenyl)ethoxy]phenyl}acrylate

(E)-ethyl 3-{4-[2-(4-{[(tert-butoxy)carbonyl]amino}phenyl)ethoxy]phenyl}acrylate

Conditions
ConditionsYield
Stage #1: triethyl phosphonoformate With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile at 20℃; for 1h; Horner-Wadsworth-Emmons Olefination;
Stage #2: tert-butyl N-{4-[2-(4-formylphenoxy)ethyl]phenyl}carbamate In acetonitrile at 20℃; for 18h; Horner-Wadsworth-Emmons Olefination;		91%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

ethyl diethoxythiophosphorylformate

ethyl diethoxythiophosphorylformate

Conditions
ConditionsYield
With Lawessons reagent In toluene at 100℃; for 2h;90%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

4-(4-nitrophenoxy)benzaldehyde
50961-54-1

4-(4-nitrophenoxy)benzaldehyde

(E)-ethyl 3-[4-(4-nitrophenoxy)phenyl]acrylate

(E)-ethyl 3-[4-(4-nitrophenoxy)phenyl]acrylate

Conditions
ConditionsYield
Stage #1: triethyl phosphonoformate With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile at 20℃; for 1h; Horner-Wadsworth-Emmons Olefination;
Stage #2: 4-(4-nitrophenoxy)benzaldehyde In acetonitrile at 20℃; for 18h; Horner-Wadsworth-Emmons Olefination;		90%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

ethoxycarbonylphosphonic acid
55920-71-3

ethoxycarbonylphosphonic acid

Conditions
ConditionsYield
With trimethylsilyl bromide at 20℃;89%
With trimethylsilyl bromide In tetrachloromethane at 0 - 20℃;
With trimethylsilyl bromide In tetrachloromethane at 20℃; for 16h;
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

disodium Ethoxycarbonylphosphonate
72305-00-1

disodium Ethoxycarbonylphosphonate

Conditions
ConditionsYield
With trimethylsilyl bromide; Amberlite IRC 50 (Na+ form) for 3h; Ambient temperature;88%
C30H54O4S2Si2
954106-06-0

C30H54O4S2Si2

triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

C31H54O6Si2
954106-09-3

C31H54O6Si2

Conditions
ConditionsYield
Stage #1: C30H54O4S2Si2 With 2,4,6-trimethyl-pyridine; methyl iodide In water; acetone at 67℃; for 13h;
Stage #2: triethyl phosphonoformate With sodium hydride In tetrahydrofuran at -15 - 20℃; for 2h; Further stages.;		85%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

cyclohexylamine
108-91-8

cyclohexylamine

diethyl (cyclohexylamino)carbonylphosphonate
174782-10-6

diethyl (cyclohexylamino)carbonylphosphonate

Conditions
ConditionsYield
In acetonitrile at 20℃; for 20h;80%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

A

triethyl phosphate
78-40-0

triethyl phosphate

B

ethylphosphonic acid diethyl ester
78-38-6

ethylphosphonic acid diethyl ester

Conditions
ConditionsYield
at 395℃; for 8h;A 79%
B 8%
6,7-difluoro-1-trifluoromethyl-1,2,3,4-tetrahydro-4-oxoquinoline
852806-63-4

6,7-difluoro-1-trifluoromethyl-1,2,3,4-tetrahydro-4-oxoquinoline

triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

ethyl 6,7-difluoro-1-trifluoromethyl-1,2,3,4-tetrahydro-4-oxo-3-quinolinecarboxylate
852806-64-5

ethyl 6,7-difluoro-1-trifluoromethyl-1,2,3,4-tetrahydro-4-oxo-3-quinolinecarboxylate

Conditions
ConditionsYield
Stage #1: 6,7-difluoro-1-trifluoromethyl-1,2,3,4-tetrahydro-4-oxoquinoline With sodium hydride In tetrahydrofuran at -78℃;
Stage #2: triethyl phosphonoformate In tetrahydrofuran for 0.5h; Heating;		78%
4-(3-nitrophenoxy)benzaldehyde

4-(3-nitrophenoxy)benzaldehyde

triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

(E)-ethyl 3-[4-(3-nitrophenoxy)phenyl]acrylate

(E)-ethyl 3-[4-(3-nitrophenoxy)phenyl]acrylate

Conditions
ConditionsYield
Stage #1: triethyl phosphonoformate With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile at 20℃; for 1h; Horner-Wadsworth-Emmons Olefination;
Stage #2: 4-(m-nitrophenoxy)benzaldehyde In acetonitrile at 20℃; for 18h; Horner-Wadsworth-Emmons Olefination;		77%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

sodium ethyl ethoxycarbonylphosphonate
72304-94-0

sodium ethyl ethoxycarbonylphosphonate

Conditions
ConditionsYield
With sodium iodide In tetrahydrofuran for 120h;76%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

7-(3,3-Dimethyl-2,4-dioxo-cyclopentyl)-hept-5-ynoic acid ethyl ester
87269-32-7

7-(3,3-Dimethyl-2,4-dioxo-cyclopentyl)-hept-5-ynoic acid ethyl ester

5-(6-Ethoxycarbonyl-hex-2-ynyl)-3,3-dimethyl-2,4-dioxo-cyclopentanecarboxylic acid ethyl ester
63315-07-1

5-(6-Ethoxycarbonyl-hex-2-ynyl)-3,3-dimethyl-2,4-dioxo-cyclopentanecarboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium hydride In dibutyl ether at 50 - 60℃;70%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

3'-azido-2',3'-deoxythymidine
30516-87-1

3'-azido-2',3'-deoxythymidine

3'-azido-3'-deoxythymidine 5'-(ethyl)(ethoxycarbonyl)phosphonate

3'-azido-3'-deoxythymidine 5'-(ethyl)(ethoxycarbonyl)phosphonate

Conditions
ConditionsYield
68%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

stavudin
3056-17-5

stavudin

2'-3'-dideoxy-2',3'-didehydrothymidine 5'-(ethyl)(ethoxycarbonyl)phosphonate

2'-3'-dideoxy-2',3'-didehydrothymidine 5'-(ethyl)(ethoxycarbonyl)phosphonate

Conditions
ConditionsYield
65%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

para-methylacetophenone
122-00-9

para-methylacetophenone

ethyl (E)-3-p-tolylbut-2-enoate
6305-61-9, 115819-11-9, 94853-53-9

ethyl (E)-3-p-tolylbut-2-enoate

Conditions
ConditionsYield
Stage #1: triethyl phosphonoformate With sodium hydride In tetrahydrofuran at 0℃; for 1.25h; Inert atmosphere;
Stage #2: para-methylacetophenone In tetrahydrofuran for 20h; Inert atmosphere; Reflux;		61%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

2-Methylacetophenone
577-16-2, 122382-54-1

2-Methylacetophenone

(E)-ethyl 3-(2-methylphenyl)-but-2-enoate
100994-06-7

(E)-ethyl 3-(2-methylphenyl)-but-2-enoate

Conditions
ConditionsYield
Stage #1: triethyl phosphonoformate With sodium hydride In tetrahydrofuran at 0℃; for 1.25h; Inert atmosphere;
Stage #2: 2-Methylacetophenone In tetrahydrofuran for 20h; Inert atmosphere; Reflux;		59%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

para-chloroacetophenone
99-91-2

para-chloroacetophenone

ethyl (E)-3-(4-chlorophenyl)-2-butenoate
21757-98-2, 81187-86-2

ethyl (E)-3-(4-chlorophenyl)-2-butenoate

Conditions
ConditionsYield
Stage #1: triethyl phosphonoformate With sodium hydride In tetrahydrofuran at 0℃; for 1.25h; Inert atmosphere;
Stage #2: para-chloroacetophenone In tetrahydrofuran for 20h; Inert atmosphere; Reflux;		57%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

5-(tert-butyl-diphenyl-silanyloxymethyl)-5-formyl-benzoic acid
269411-93-0

5-(tert-butyl-diphenyl-silanyloxymethyl)-5-formyl-benzoic acid

5-(t-butyl-diphenyl-silanyloxymethyl)-5-(2-ethoxycarbonyl-vinyl)-benzoic acid

5-(t-butyl-diphenyl-silanyloxymethyl)-5-(2-ethoxycarbonyl-vinyl)-benzoic acid

Conditions
ConditionsYield
With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 23℃;51%
3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

(E)-3,4,4-trimethyl-1-pent-2-enoic acid ethyl ester
21016-48-8, 91140-23-7, 16812-82-1

(E)-3,4,4-trimethyl-1-pent-2-enoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: triethyl phosphonoformate With sodium hydride In tetrahydrofuran at 0℃; for 1.25h; Inert atmosphere;
Stage #2: 3,3-dimethyl-butan-2-one In tetrahydrofuran for 20h; Inert atmosphere; Reflux;		47%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

benzylamine
100-46-9

benzylamine

C12H18NO4P

C12H18NO4P

Conditions
ConditionsYield
at 20℃; for 2h; Substitution;36%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

(E)-ethyl 3-(4-methoxyphenyl)but-2-enoate
7706-82-3

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

Conditions
ConditionsYield
Stage #1: triethyl phosphonoformate With sodium hydride In tetrahydrofuran at 0℃; for 1.25h; Inert atmosphere;
Stage #2: 1-(4-methoxyphenyl)ethanone In tetrahydrofuran for 20h; Inert atmosphere; Reflux;		35%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

2,2-dimethylpropiophenone
938-16-9

2,2-dimethylpropiophenone

(Z)-ethyl 4,4-dimethyl-3-phenylpent-2-enoate
77920-99-1

(Z)-ethyl 4,4-dimethyl-3-phenylpent-2-enoate

Conditions
ConditionsYield
Stage #1: triethyl phosphonoformate With sodium hydride In tetrahydrofuran at 0℃; for 1.25h; Inert atmosphere;
Stage #2: 2,2-dimethylpropiophenone In tetrahydrofuran for 20h; Inert atmosphere; Reflux;		29%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

Cyclohexyl phenyl ketone
712-50-5

Cyclohexyl phenyl ketone

ethyl (2E)-3-cyclohexyl-3-phenyl prop-2-enoate
87666-40-8

ethyl (2E)-3-cyclohexyl-3-phenyl prop-2-enoate

Conditions
ConditionsYield
Stage #1: triethyl phosphonoformate With sodium hydride In tetrahydrofuran at 0℃; for 1.25h; Inert atmosphere;
Stage #2: Cyclohexyl phenyl ketone In tetrahydrofuran for 20h; Inert atmosphere; Reflux;		29%
triethyl phosphonoformate
1474-78-8

triethyl phosphonoformate

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

(2E)-ethyl 3,5-dimethyl-2-hexenoate
16812-83-2

(2E)-ethyl 3,5-dimethyl-2-hexenoate

Conditions
ConditionsYield
Stage #1: triethyl phosphonoformate With sodium hydride In tetrahydrofuran at 0℃; for 1.25h; Inert atmosphere;
Stage #2: 4-methyl-2-pentanone In tetrahydrofuran for 20h; Inert atmosphere; Reflux;		20%

Ethyl diethoxyphosphinylformate Chemical Properties

Molecular Structure:

Molecular Formula: C7H15O5P
Molecular Weight: 210.1648
IUPAC Name: Ethyl diethoxyphosphorylformate
Synonyms of Ethyl diethoxyphosphinylformate (CAS NO.1474-78-8): AI3-18561 ; Diethyl carbethoxyphosphonate ; Diethyl ethoxycarbonylphosphonate ; EINECS 216-016-8 ; Formic acid, phosphono-, triethyl ester ; NSC 108684 ; Phosphinecarboxylic acid, diethoxy-, ethyl ester, oxide ; Triethyl carboxyphosphonate ; Triethyl phosphonoformate ; Triethyl phosphonomethanoate ; Diethyoxyphosphinecarboxylic acid, ethyl ester, oxide ; Phosphinecarboxylic acid, 1,1-diethoxy-, ethyl ester, 1-oxide
CAS NO: 1474-78-8
Product Categories: Organic Building Blocks ; Phosphonates/Phosphinates ; Phosphorus Compounds 
Index of Refraction: 1.419
Molar Refractivity: 46.61 cm3
Molar Volume: 184.4 cm3
Surface Tension: 34.4 dyne/cm
Density: 1.139 g/cm3
Flash Point: 128 °C
Enthalpy of Vaporization: 50.28 kJ/mol
Boiling Point: 264.9 °C at 760 mmHg
Vapour Pressure of Ethyl diethoxyphosphinylformate (CAS NO.1474-78-8): 0.00947 mmHg at 25°C

Ethyl diethoxyphosphinylformate Safety Profile

Hazard Codes of Ethyl diethoxyphosphinylformate (CAS NO.1474-78-8): IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36/37-26 
S24/25: Avoid contact with skin and eyes. 
S36/37: Wear suitable protective clothing and gloves. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3

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