Dimethyl methylphosphonate

Dimethyl methylphosphonate
IUPAC name (methoxy-methylphosphoryl)oxymethane
Identifiers
CAS number	756-79-6 Y
PubChem	12958
ChemSpider	12418 Y
Jmol-3D images	Image 1
SMILES O=P(OC)(OC)C
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
Properties
Molecular formula	C3H9O3P
Molar mass	124.08 g mol−1
Appearance	colorless liquid
Melting point	-50 °C, 223 K, -58 °F
Boiling point	181 °C, 454 K, 358 °F
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Dimethyl methylphosphonate, or methylphosphonic acid dimethyl ester (DMMP), is a colorless liquid with chemical formula C₃H₉O₃P or CH₃PO(OCH₃)₂. It is combustible. It emits a distinct odor. It can be found in household radiators, especially those installed in the former Soviet Bloc. In contact with water it slowly undergoes hydrolysis. May soften some plastics and rubbers. Its other names are dimethoxymethyl phosphine oxide, dimethyl methanephosphonate, dimethyl methyl phosphonate, Fran TF 2000, Fyron DMMP, Metaran, NSC 62240, O,O-dimethyl methylphosphonate, and Reoflam DMMP.

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 910,000 kg).^{[citation needed]}

Dimethyl methylphosphonate is not classified as toxic, but is harmful if inhaled, swallowed or absorbed through the skin; it is a Chemical Weapons Convention schedule 2 chemical used in the synthesis of sarin nerve gas. It can also be used as standalone as a simulant for sarin training exercises and for calibration of detectors. It is a suspected carcinogen.

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

See also

• Nerve agent precursor: Dimethyl methyl phosphonate