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Dimethyl methylphosphonate

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Title: Dimethyl methylphosphonate  
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Subject: Phosphonate, Antistatic agents, Chemical weapons, Fuel additives, List of Schedule 2 substances (CWC)
Collection: Antistatic Agents, Chemical Weapons, Flame Retardants, Fuel Additives, Methyl Esters, Phosphonate Esters, Plasticizers
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Dimethyl methylphosphonate

Dimethyl methylphosphonate
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
 Y
ChemSpider  Y
Jmol-3D images Image
PubChem
Properties
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)
slowly hydrolyses
Hazards
Main hazards Toxic
R-phrases R46, R36
Flash point 69 °C (156 °F; 342 K) closed cup
Lethal dose or concentration (LD, LC):
LD50 (Median dose)
  • Oral (rat) 8,210 mg/kg
  • Inhalation (rat) 1h 20.13 mg/l
  • Dermal (rabbit) >2,000 mg/kg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)


Dimethyl methylphosphonate is an 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.[1] 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 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.

References

  1. ^ Maier, Ludwig (1990). "ORGANIC PHOSPHORUS COMPOUNDS 90.l A CONVENIENT, ONE-STEP SYNTHESIS OF ALKYL- AND ARYLPHOSPHONYL DICHLORIDES". Phosphorus, Sulfur, and Silicon and the Related Elements 47 (3-4): 465–470.  
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