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867-13-0

Basic Information
CAS No.: 867-13-0
Name: Triethyl phosphonoacetate
Article Data: 101
Molecular Structure:
Molecular Structure of 867-13-0 (Triethyl phosphonoacetate)
Formula: C8H17O5P
Molecular Weight: 224.194
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;
EINECS: 212-757-6
Density: 1.13 g/cm3
Melting Point: -24 °C
Boiling Point: 287.4 °C at 760 mmHg
Flash Point: 141.6 °C
Solubility: Slightly miscible with water.
Appearance: colorless to light yellow liquid
Hazard Symbols: DangerousN,IrritantXi,HarmfulXn
Risk Codes: 51/53-36/37/38
Safety: 61-37/39-26-36
Transport Information: UN 3082 9/PG 3
PSA: 71.64000
LogP: 1.81560
Synthetic route
105-36-2

ethyl bromoacetate

122-52-1

triethyl phosphite

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%
105-39-5

chloroacetic acid ethyl ester

122-52-1

triethyl phosphite

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%
105-39-5

chloroacetic acid ethyl ester

867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

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

triethyl phosphate

105-36-2

ethyl bromoacetate

867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
at 140℃; for 3h;88%
623-73-4

diazoacetic acid ethyl ester

762-04-9

phosphonic acid diethyl 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%
105-39-5

chloroacetic acid ethyl ester

762-04-9

phosphonic acid diethyl 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%
78-94-4

methyl vinyl ketone

66700-63-8

diethyl 1-iodo-1-carbethoxy-methylphosphonate

A

867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

B

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%
683-08-9

Diethyl methylphosphonate

XC(O)OC2H5

XC(O)OC2H5

867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

Conditions
ConditionsYield
With n-butyllithium; lithium diisopropyl amide In tetrahydrofuran; hexane at -60℃;74%
132646-34-5

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

A

867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

B

159017-57-9

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

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

Methyl diethylphosphonoacetate

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

867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

B

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

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
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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.