Product Name

  • Name

    Trimethyl phosphonoacetate

  • EINECS 227-663-0
  • CAS No. 5927-18-4
  • Article Data12
  • CAS DataBase
  • Density 1.125 g/cm3
  • Solubility Slightly miscible with water.
  • Melting Point 242 °C
  • Formula C5H11O5P
  • Boiling Point 311 ºC at 760 mmHg
  • Molecular Weight 182.113
  • Flash Point 109.7 °C
  • Transport Information
  • Appearance clear colorless to light yellow liquid
  • Safety 23-24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 5927-18-4 (Trimethyl phosphonoacetate)
  • Hazard Symbols
  • Synonyms Acetic acid, phosphono-,trimethyl ester (7CI,8CI);(Carboxymethyl)phosphonic acid trimethyl ester;(Dimethoxyphosphinyl)acetic acid methyl ester;Carbomethoxymethanephosphonicacid dimethyl ester;Dimethyl methoxycarbonylmethanephosphonate;Methyl (dimethoxyphosphinyl)acetate;Methyl 2-(dimethylphosphono)acetate;Methyl dimethylphosphonoacetate;NSC 84262;Phosphonoacetic acid trimethylester;[(Methoxycarbonyl)methyl]dimethylphosphonate;
  • PSA 71.64000
  • LogP 0.64530

Synthetic route

methanol
67-56-1

methanol

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate
88738-78-7

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

A

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

B

methyl methyl(2,2,2-trifluoroethyl)phosphonoacetate
681123-85-3

methyl methyl(2,2,2-trifluoroethyl)phosphonoacetate

Conditions
ConditionsYield
With triethylamine at 20℃; for 0.5h;A 7%
B 88%
...Expand
bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

Conditions
ConditionsYield
at 100℃; for 12h;74%
methyl chloroacetate
96-34-4

methyl chloroacetate

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

Conditions
ConditionsYield
Heating;70%
methyl diazoacetate
6832-16-2

methyl diazoacetate

Dimethyl phosphite
868-85-9

Dimethyl phosphite

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

Conditions
ConditionsYield
With copper acetylacetonate In benzene Heating;60%
methanol
67-56-1

methanol

ethyl diphenylphosphonoacetate
16139-79-0

ethyl diphenylphosphonoacetate

A

ethyl 2-(dimethoxyphosphoryl)acetate
311-46-6

ethyl 2-(dimethoxyphosphoryl)acetate

B

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

C

methyl methylphenylphosphonoacetate
625396-69-2

methyl methylphenylphosphonoacetate

D

ethyl methylphenylphosphonoacetate
625396-71-6, 852573-54-7

ethyl methylphenylphosphonoacetate

Conditions
ConditionsYield
With sodium hydroxide at 20℃; for 0.666667h;A 2%
B 13%
C 32%
D 7%
...Expand
methanol
67-56-1

methanol

phosphonoacetic acid
4408-78-0

phosphonoacetic acid

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

Conditions
ConditionsYield
(i) PCl5, (ii) /BRN= 1098229/, Et3N; Multistep reaction;
methanol
67-56-1

methanol

(2-chloro-2-ethoxy-vinyl)-phosphonic acid dichloride
42451-44-5

(2-chloro-2-ethoxy-vinyl)-phosphonic acid dichloride

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

Conditions
ConditionsYield
In diethyl ether
methyl chloroacetate
96-34-4

methyl chloroacetate

Dimethyl phosphite
868-85-9

Dimethyl phosphite

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

Conditions
ConditionsYield
With potassium carbonate at 20 - 30℃;
2-methylnicotinaldehyde
60032-57-7

2-methylnicotinaldehyde

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

methyl (E)/(Z)-3-(2-methyl-3-pyridyl)propenoate
137146-28-2, 137146-29-3

methyl (E)/(Z)-3-(2-methyl-3-pyridyl)propenoate

Conditions
ConditionsYield
With potassium carbonate In water for 4h; Ambient temperature;100%
2-methylbut-2-enal
497-03-0

2-methylbut-2-enal

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

methyl (2E,4E)-4-methyl-2,4-hexadienoate
57258-50-1

methyl (2E,4E)-4-methyl-2,4-hexadienoate

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With sodium hydride In benzene at 20℃; for 1.33333h;
Stage #2: 2-methylbut-2-enal In benzene for 0.5h; Heating;		100%
With sodium hydride 1.) THF, 2.) RT, 9 h; Multistep reaction;
With sodium hydride In benzene at 65℃; for 4h;37.82 g
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

1,3-Diphenylpropanone

1,3-Diphenylpropanone

4-Phenyl-3-(phenylmethyl)-2-butenoic acid methyl ester
157731-51-6

4-Phenyl-3-(phenylmethyl)-2-butenoic acid methyl ester

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In diethyl ether; hexane 1.) -20 deg C, 20 min, 2.) r.t., 50 h;100%
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

3-(4-methoxy-phenyl)acrylic acid methyl ester
3901-07-3

3-(4-methoxy-phenyl)acrylic acid methyl ester

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Metallation;
Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Condensation; Horner-Wadsworth-Emmons reaction;		100%
Stage #1: trimethyl phosphonoacetate With n-butyllithium In tetrahydrofuran at -78℃;
Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at -78 - 20℃; Horner-Wadsworth-Emmons reaction;
In tetrahydrofuran; hexane for 1h; Horner-Wadsworth-Emmons Olefination; Cooling with ice;
furfural
98-01-1

furfural

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

methyl 3-(2-furyl)acrylate
58293-85-9

methyl 3-(2-furyl)acrylate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0℃;100%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0℃; Metallation;
Stage #2: furfural In tetrahydrofuran for 0.166667h; Condensation;		90%
With 2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane In tetrahydrofuran at 20℃; for 2.2h; Inert atmosphere; optical yield given as %de; stereoselective reaction;84%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

methyl 2-(bis((trimethylsilyl)oxy)phosphoryl)acetate
67605-34-9

methyl 2-(bis((trimethylsilyl)oxy)phosphoryl)acetate

Conditions
ConditionsYield
at 80℃; for 96h; Inert atmosphere;100%
In chlorobenzene at 130℃; for 8h;
at 80℃; for 96h; Inert atmosphere;
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

(1S,3aS,5S,7aR)-3a-hydroxy-5-cyclohexyl-7a-methylperhydroindene-1-carboxaldehyde
178379-71-0

(1S,3aS,5S,7aR)-3a-hydroxy-5-cyclohexyl-7a-methylperhydroindene-1-carboxaldehyde

methyl (1R,3aS,5S,7aR)-5-cyclohexyl-3a-hydroxy-7a-methylperhydroindene-1-yl-(E)-acrylate
392235-25-5

methyl (1R,3aS,5S,7aR)-5-cyclohexyl-3a-hydroxy-7a-methylperhydroindene-1-yl-(E)-acrylate

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0℃; for 1h;
Stage #2: (1S,3aS,5S,7aR)-3a-hydroxy-5-cyclohexyl-7a-methylperhydroindene-1-carboxaldehyde In tetrahydrofuran at 20℃; for 2h; Horner-Emmons reaction; Further stages.;		100%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

2-(1-azabicyclo[2.2.2]oct-3-ylidene)acetic acid methyl ester
94764-01-9

2-(1-azabicyclo[2.2.2]oct-3-ylidene)acetic acid methyl ester

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Wittig Olefination; Inert atmosphere;
Stage #2: 3-Quinuclidinone In tetrahydrofuran; mineral oil at 20℃; Wittig Olefination; Inert atmosphere;		100%
Stage #1: trimethyl phosphonoacetate With sodium In methanol at 0℃; for 1h;
Stage #2: 3-Quinuclidinone In methanol at 0℃; for 0.5h; Horner-Wadsworth-Emmons reaction;
Stage #3: In methanol at 50℃; for 18h;
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0 - 20℃;
Stage #2: 3-Quinuclidinone In tetrahydrofuran at 0 - 20℃; Wadsworth-Emmons reaction;
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h;
Stage #2: 3-Quinuclidinone In tetrahydrofuran; mineral oil at 20℃; for 18h;
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

4-(2-oxo-2-quinolin-3-yl-ethyl)-piperidine-1-carboxylic acid tert-butyl ester
669075-94-9

4-(2-oxo-2-quinolin-3-yl-ethyl)-piperidine-1-carboxylic acid tert-butyl ester

4-(3-methoxycarbonyl-2-quinolin-3-ylallyl)piperidine-1-carboxylic acid tert-butyl ester
669075-95-0

4-(3-methoxycarbonyl-2-quinolin-3-ylallyl)piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With sodium hexamethyldisilazane In tetrahydrofuran for 4h; Heating;100%
furan-3-carboxaldehyde
498-60-2

furan-3-carboxaldehyde

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

Methyl 3-(3'-furanyl)prop-2-en-1-oate
99595-62-7

Methyl 3-(3'-furanyl)prop-2-en-1-oate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0℃;100%
3-thiophene carboxaldehyde
498-62-4

3-thiophene carboxaldehyde

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

3-Thiophen-3-yl-acrylic Acid Methyl Ester
75754-85-7

3-Thiophen-3-yl-acrylic Acid Methyl Ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0℃;100%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran for 1h;
Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran at 20℃; for 18h;		94%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 2h; Inert atmosphere;
Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;		81%
3-(4-methoxyphenoxy)-3-perfluoropentyl-prop-2-enal

3-(4-methoxyphenoxy)-3-perfluoropentyl-prop-2-enal

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

methyl (EE)-5-(4-methoxyphenoxy)-5-perfluoropentyl-2,4-pentadienoate

methyl (EE)-5-(4-methoxyphenoxy)-5-perfluoropentyl-2,4-pentadienoate

Conditions
ConditionsYield
With sodium hydride In methanol at 20℃; for 2h; Wadsworth-Emmons reaction;100%
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

methyl (E)-4-carboxyl cinnamate
115974-97-5

methyl (E)-4-carboxyl cinnamate

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate; 4-Carboxybenzaldehyde With potassium carbonate In water at 0 - 20℃; for 1.5h;
Stage #2: In water pH=1; Acidic aqueous solution;		100%
With potassium carbonate In water at 0 - 20℃; pH=Ca. 2;95%
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

m-formylphenyl benzoic acid
619-21-6

m-formylphenyl benzoic acid

(E)-3-(methoxy-3-oxoprop-1-en-1-yl)benzoic acid
115974-96-4

(E)-3-(methoxy-3-oxoprop-1-en-1-yl)benzoic acid

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate; m-formylphenyl benzoic acid With potassium carbonate In water at 0 - 20℃; for 17h;
Stage #2: In water pH=1; Acidic aqueous solution;		100%
With potassium carbonate In water at 0 - 20℃; pH=Ca. 2;93%
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

2-ethoxy-4-nitro-benzaldehyde
1134-43-6

2-ethoxy-4-nitro-benzaldehyde

ethyl 4-nitro-2-ethoxycinnamate
863885-81-8

ethyl 4-nitro-2-ethoxycinnamate

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 2-ethoxy-4-nitro-benzaldehyde In tetrahydrofuran at 20℃; for 4h; Wittig-Horner Reaction; Inert atmosphere;		100%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0℃;
Stage #2: 2-ethoxy-4-nitro-benzaldehyde In tetrahydrofuran at 0 - 20℃; for 15h;		99%
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 15h;
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

4-(4-hydroxyphenyl)cyclohexan-1-one
105640-07-1

4-(4-hydroxyphenyl)cyclohexan-1-one

[4-(4-hydroxyphenyl)cyclohexylidene]acetic acid methyl ester
701232-66-8

[4-(4-hydroxyphenyl)cyclohexylidene]acetic acid methyl ester

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With sodium hydride In mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: 4-(4-hydroxyphenyl)cyclohexan-1-one In tetrahydrofuran; mineral oil at 20℃; for 0.416667h; Inert atmosphere;		100%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 2.83333h; Inert atmosphere;100%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere;
Stage #2: 4-(4-hydroxyphenyl)cyclohexan-1-one In tetrahydrofuran; mineral oil at 25℃; for 5h;		97%
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

(2R)-2-(1,1-dimethylethoxycarbonylamino)-2-cyclohexylethanal
171560-20-6

(2R)-2-(1,1-dimethylethoxycarbonylamino)-2-cyclohexylethanal

(R)-4-tert-butoxycarbonylamino-4-cyclohexyl-but-2-enoic acid methyl ester
876761-53-4

(R)-4-tert-butoxycarbonylamino-4-cyclohexyl-but-2-enoic acid methyl ester

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 5℃; for 1h; Inert atmosphere;
Stage #2: (2R)-2-(1,1-dimethylethoxycarbonylamino)-2-cyclohexylethanal In tetrahydrofuran; mineral oil at 0 - 20℃;		100%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h;
Stage #2: (2R)-2-(1,1-dimethylethoxycarbonylamino)-2-cyclohexylethanal In tetrahydrofuran at 0 - 20℃; for 0.333333h;
p-benzyloxybenzaldehyde
4397-53-9

p-benzyloxybenzaldehyde

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

(E)-methyl 3-(4-(benzyloxy)phenyl)acrylate
84184-51-0

(E)-methyl 3-(4-(benzyloxy)phenyl)acrylate

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 0℃;
Stage #2: p-benzyloxybenzaldehyde In tetrahydrofuran; mineral oil at 20℃;		100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

(E)-methyl 3-(pyridine-4-yl)prop-2-enoate
81124-49-4

(E)-methyl 3-(pyridine-4-yl)prop-2-enoate

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 5h;100%
tert-butoxycarbonylamino-[4-(4-formylphenoxy)-phenyl]-acetic acid
918337-11-8

tert-butoxycarbonylamino-[4-(4-formylphenoxy)-phenyl]-acetic acid

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

3-{4-[4-(tert-butoxycarbonylaminocarboxymethyl)-phenoxy]-phenyl}-acrylic acid methyl ester
918337-12-9

3-{4-[4-(tert-butoxycarbonylaminocarboxymethyl)-phenoxy]-phenyl}-acrylic acid methyl ester

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0 - 5℃; for 0.0833333h;
Stage #2: tert-butoxycarbonylamino-[4-(4-formylphenoxy)-phenyl]-acetic acid In tetrahydrofuran at 0 - 20℃; for 0.5h;
Stage #3: With hydrogenchloride; citric acid In tetrahydrofuran; water pH=~ 2;		100%
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

2-(trifluoromethoxy)benzaldehyde
94651-33-9

2-(trifluoromethoxy)benzaldehyde

methyl (2E)-3-[2-(trifluoromethoxy)phenyl]prop-2-enoate
1202578-19-5

methyl (2E)-3-[2-(trifluoromethoxy)phenyl]prop-2-enoate

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #2: 2-(trifluoromethoxy)benzaldehyde In tetrahydrofuran at 20℃; Inert atmosphere;		100%
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

C13H19NO2

C13H19NO2

C16H23NO3

C16H23NO3

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; Horner-Wadsworth-Emmons Olefination;100%
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

methyl (E)-3-(2-methylphenyl)-2-propenoate
70625-62-6, 75950-75-3, 130451-86-4

methyl (E)-3-(2-methylphenyl)-2-propenoate

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: 2-methylphenyl aldehyde In tetrahydrofuran; paraffin oil at -78 - 20℃; Inert atmosphere;		100%
With sodium methylate In methanol; N,N-dimethyl-formamide Wittig-Horner Reaction;
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
101385-93-7

3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

tert-butyl 3-(2-methoxy-2-oxoethylidene)pyrrolidine-1-carboxylate
441773-67-7

tert-butyl 3-(2-methoxy-2-oxoethylidene)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h;
Stage #2: 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester In tetrahydrofuran; mineral oil at 0 - 20℃; for 16h;		100%
Stage #1: trimethyl phosphonoacetate With potassium tert-butylate In tetrahydrofuran at 0℃; for 2.5h;
Stage #2: 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester In tetrahydrofuran at 0℃; for 1h;		92.8%
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

m-tolyl aldehyde
620-23-5

m-tolyl aldehyde

(E)-methyl 3-methylcinnamate
82444-40-4, 118315-74-5, 95416-56-1

(E)-methyl 3-methylcinnamate

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: m-tolyl aldehyde In tetrahydrofuran; paraffin oil at -78 - 20℃; Inert atmosphere;		100%
piperonal
120-57-0

piperonal

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate
40918-96-5

methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: piperonal In tetrahydrofuran; paraffin oil at -78 - 20℃; Inert atmosphere;		100%
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

3-p-tolyl-acrylic acid methyl ester
20754-20-5

3-p-tolyl-acrylic acid methyl ester

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: 4-methyl-benzaldehyde In tetrahydrofuran; paraffin oil at -78 - 20℃; Inert atmosphere;		100%
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

2-(8-phenyloctyl) benzaldehyde
96964-45-3

2-(8-phenyloctyl) benzaldehyde

methyl 3-<2-(8-phenyloctyl)phenyl>propenoate
145950-31-8

methyl 3-<2-(8-phenyloctyl)phenyl>propenoate

Conditions
ConditionsYield
99%
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

(2S,3S)-3-(tert-Butyl-diphenyl-silanyl)-oxirane-2-carbaldehyde
178391-54-3

(2S,3S)-3-(tert-Butyl-diphenyl-silanyl)-oxirane-2-carbaldehyde

(E)-3-[(2S,3S)-3-(tert-Butyl-diphenyl-silanyl)-oxiranyl]-acrylic acid methyl ester

(E)-3-[(2S,3S)-3-(tert-Butyl-diphenyl-silanyl)-oxiranyl]-acrylic acid methyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile for 0.5h; Ambient temperature;99%
trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

4-methoxy-1-naphthaldehyde
15971-29-6

4-methoxy-1-naphthaldehyde

methyl-3-(4-methoxy-1-naphthyl)-E-propenoate

methyl-3-(4-methoxy-1-naphthyl)-E-propenoate

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.25h;
Stage #2: 4-methoxy-1-naphthaldehyde In dichloromethane at 20℃; for 36h;		99%
Stage #1: trimethyl phosphonoacetate With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.25h;
Stage #2: 4-methoxy-1-naphthaldehyde In dichloromethane at 0 - 20℃; for 36h;		99%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; Horner-Wadsworth-Emmons reaction;89%

Trimethyl phosphonoacetate Specification

The IUPAC name of Trimethylacetyl phosphate is methyl 2-dimethoxyphosphorylacetate. With the CAS registry number 5927-18-4, it is also named as Acetic acid, (dimethoxyphosphinyl)-, methyl ester; Phosphonoacetic acid trimethyl ester. The product's categories are horner-emmons reaction, synthetic organic chemistry, wittig & horner-emmons reaction, C-C bond formation, horner-wadsworth-emmons reagents and olefination. It is clear colorless to light yellow liquid. And people should not breathe the vapour of this chemical and avoid contact with skin and eyes.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.68; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.68; (4)ACD/LogD (pH 7.4): -0.68; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 10.2; (8)ACD/KOC (pH 7.4): 10.2; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.407; (13)Molar Refractivity: 37.35 cm3; (14)Molar Volume: 151.4 cm3; (15)Polarizability: 14.8×10-24 cm3; (16)Surface Tension: 34.6 dyne/cm; (17)Enthalpy of Vaporization: 55.19 kJ/mol; (18)Vapour Pressure: 0.000577 mmHg at 25°C; (19)Rotatable Bond Count: 5; (20)Exact Mass: 182.03441; (21)MonoIsotopic Mass: 182.03441; (22)Topological Polar Surface Area: 61.8; (23)Heavy Atom Count: 11.

Preparation of Trimethylacetyl phosphate: It can be obtained by bromoacetic acid methyl ester and phosphorous acid trimethyl ester. The reaction temperature is 100 °C and the reaction time is 12 hours. The yield is 74%.

Uses of Trimethylacetyl phosphate: It is an important Wittig-horner reagent and it is also used as an important intermediate in the manufacture of vitamin compounds, drugs, insect pheromones and other natural compounds. It is also can be used in many organic synthesis. For example: It reacts with cyclohexanone to get cyclohexylidene-acetic acid methyl ester. This reaction needs reagent NaH and solvent tetrahydrofuran.

People can use the following data to convert to the molecule structure.
1. SMILES: O=C(OC)CP(=O)(OC)OC;
2. InChI: InChI=1/C5H11O5P/c1-8-5(6)4-11(7,9-2)10-3/h4H2,1-3H3.

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