Dimethyl methylphosphonate

Dimethyl methylphosphonate

150px
150px
Names
IUPAC name (methoxy-methylphosphoryl)oxymethane
Other names methylphosphonic acid dimethyl ester dimethoxymethyl phosphine oxide dimethyl methanephosphonate dimethyl methyl phosphonate Fran TF 2000 Fyron DMMP Metaran NSC 62240 O,O-dimethyl methylphosphonate Reoflam DMMP
Identifiers
CAS Number	756-79-6 Y
ChemSpider	12418 Y
Jmol 3D model	Interactive image
PubChem	12958
InChI InChI=1S/C3H9O3P/c1-5-7(3,4)6-2/h1-3H3 Y Key: VONWDASPFIQPDY-UHFFFAOYSA-N Y InChI=1/C3H9O3P/c1-5-7(3,4)6-2/h1-3H3 Key: VONWDASPFIQPDY-UHFFFAOYAG
SMILES O=P(OC)(OC)C
Properties
Chemical formula	C3H9O3P
Molar mass	124.08 g·mol−1
Appearance	colourless liquid
Density	1.145 g/mL at 25 °C
Melting point	−50 °C (−58 °F; 223 K)
Boiling point	181 °C (358 °F; 454 K)
Solubility in water	slowly hydrolyses
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Dimethyl methylphosphonate is an organophosphorus compound with the chemical formula C₃H₉O₃P or CH₃PO(OCH₃)₂. It is a colourless liquid which is primarily used as a flame retardant.

Chemistry

Dimethyl methylphosphonate can be prepared from trimethyl phosphite and a halomethane (e.g. iodomethane) via the Michaelis–Arbuzov reaction.

Dimethyl methylphosphonate is a schedule 2 chemical as it may be used in the production of chemical weapons. It will react with thionyl chloride to produce methylphosphonic acid dichloride, which is used in the production of sarin and soman nerve agents. Various amines can be used to catalyse this process. It can be used as a sarin-simulant for the calibration of organophosphorus detectors.

Uses

The primary commercial use of dimethyl methylphosphonate is as a flame retardant. Other commercial uses are a preignition additive for gasoline, anti-foaming agent, plasticizer, stabilizer, textile conditioner, antistatic agent, and an additive for solvents and low-temperature hydraulic fluids. It can be used as a catalyst and a reagent in organic synthesis, as it can generate a highly reactive ylide. The yearly production in the United States varies between 100 and 1,000 short tons (91,000 and 907,000 kg).

About 190 liters of dimethyl methylphosphonate, together with other chemicals, were released during the El Al Flight 1862 crash at Bijlmer, Amsterdam.