Methyl (diethylphosphono)acetate
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Methyl (diethylphosphono)acetate
structure -
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CAS No:
1067-74-9
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Formula:
C7H15O5P
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Chemical Name:
Methyl (diethylphosphono)acetate
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Synonyms:
Acetic acid,2-(diethoxyphosphinyl)-,methyl ester;Acetic acid,phosphono-,P,P-diethyl methyl ester;Acetic acid,(diethoxyphosphinyl)-,methyl ester;Acetic acid,phosphono-,diethyl 1-methyl ester;Diethylphosphonoacetic acid methyl ester;Diethyl methoxycarbonylmethanephosphonate;Diethyl carbomethoxymethylphosphonate;Diethyl phosphonate,methoxycarbonylmethyl-;Methyl (diethylphosphono)acetate;O,O-Diethyl phosphonoacetic acid methyl ester;(Methoxycarbonylmethyl) diethoxyphosphine oxide;Methoxycarbonylmethanephosphonic acid diethyl ester;Methyl diethoxyphosphonoacetate;Methyl di-O-ethylphosphonoacetate;Diethyl (methoxycarbonylmethyl)phosphonate;[(Methoxycarbonyl)methyl]phosphonic acid diethyl ester;Methyl 2-(diethylphosphonato)acetate;(Diethoxyphosphinyl)acetic acid methyl ester;Methyl (diethoxyphosphinyl)acetate;NSC 147757;Methyl 2-(diethylphosphono)acetate;Methyl 2-(diethoxyphosphono)acetate;Methyl 2-(diethoxyphosphinyl)acetate;Methyl 2-(diethoxyphosphoryl)acetate
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CAS No:
Methyl (diethylphosphono)acetate Basic Attributes
210.16
210.16
1782397
213-938-2
147757
DTXSID50147732
29310095
Characteristics
61.8
0.1
Clear colorless to faint yellow Liquid
1.1611 g/cm3 @ Temp: 20 °C
99 °C @ Press: 1 Torr
>230 °F
1.419
Miscible with tetrahydrofuran.
Store at<= 20°C.
0mmHg at 25°C
Safety Information
NONH for all modes of transport
3
36/37/38
26-36
Xi
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (97.78%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 45 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Methyl (diethylphosphono)acetate Use and Manufacturing
General procedure: TMSBr (90 L, 0.691 mmol) was added at r.t. to a solution of trimethyl phosphonoacetate (2; 50.3mg, 0.276 mmol) in anhydrous CH2Cl2 (0.55 mL). After stirring at r.t. for 5 h under argon, evaporation of the reaction mixture in vacuo gave methyl2-{bis[(trimethylsilyl)oxy]phosphoryl}acetate (4), which was used without further purification.Ph3P (181 mg, 0.691 mmol) and I2 (175 mg, 0.691 mmol) were added to a solution of 4 in anhydrous CHCl3 (1.8 mL) at r.t. under argon. After stirring at r.t. for 15 min under argon, imidazole(188 mg, 2.76 mmol) was added. The reaction mixture was stirred for 15 min at r.t. and then for 30min at 50 °C. Afterwards, 2, 2, 2-trifluoroethanol (79 l, 1.10 mmol) was added and the reactionmixture was stirred at 60 °C for 5 h. After filtration of the reaction mixture, the filtrate wasevaporated in vacuo to give a crude product 1, which was purified by column chromatography[Silica Gel PSQ 60B: n-hexane–EtOAc (2:1)] to afford 1 (82.3 mg, 94percent) as a colorless oil.A mixture of methyl chloroacetate (4.8 g, 44 mmol) and triethylphosphite (7.3 g, 44 mmol) was heated at 135 °C for 10 h. The mixture was allowed to cool to room temperature to afford the desired product, methyl 2-(diethylphosphoryl)acetate, in 98percent yield (6.2 g) as a mixture of rotamers.
It is an important type of Wittig-horner reagent, which can be used as a plasticizer, fire retardant and extractant, etc. It is also an important intermediate for the manufacture of natural compounds such as vitamins, drugs, insect pheromones and so on.
Computed Properties
Molecular Weight:210.16
XLogP3:0.1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:210.06571057
Monoisotopic Mass:210.06571057
Topological Polar Surface Area:61.8
Heavy Atom Count:13
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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Methyl (diethylphosphono)acetate
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