Dimethyl methylphosphonate

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Dimethyl methylphosphonate
Names
Preferred IUPAC name
Dimethyl methylphosphonate
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
  • {[methoxy(methyl)phosphoryl]oxy}methane
  • Reoflam DMMP
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
 100.010.957 Edit this at Wikidata
EC Number
  • 212-052-3
UNII
UN number 1993
  • InChI=1S/C3H9O3P/c1-5-7(3,4)6-2/h1-3H3 checkY
    Key: VONWDASPFIQPDY-UHFFFAOYSA-N checkY
  • InChI=1/C3H9O3P/c1-5-7(3,4)6-2/h1-3H3
    Key: VONWDASPFIQPDY-UHFFFAOYAG
  • O=P(OC)(OC)C
Properties
C3H9O3P
Molar mass 124.076 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[1]
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
GHS labelling:
GHS07: Exclamation markGHS08: Health hazard
Warning
H319, H340, H361f
P201, P305+P351+P338, P308+P310
Flash point 69 °C (156 °F; 342 K) closed cup
Lethal dose or concentration (LD, LC):
  • 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).
checkY verify (what is checkY☒N ?)

Dimethyl methylphosphonate is an

organophosphorus compound
with the chemical formula CH3PO(OCH3)2. It is a colourless liquid, which is primarily used as a flame retardant.

Synthesis

Dimethyl methylphosphonate can be prepared from trimethyl phosphite and a halomethane (e.g. iodomethane) via the Michaelis–Arbuzov reaction.[2]

Dimethyl methylphosphonate is a

methylphosphonic acid dichloride, which is used in the production of sarin and soman nerve agents. Various amines can be used to catalyse this process.[3]
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

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).[citation needed
]

About 190 liters of dimethyl methylphosphonate, together with other chemicals, were released during the crash of El Al Flight 1862 at Bijlmer in Amsterdam in 1992.[5][6]

References

  1. ^ "GESTIS-Stoffdatenbank". gestis.dguv.de.
  2. S2CID 73412537
    .
  3. doi:10.1080/10426509008038002
    .
  4. ^ "Product Stewardship Summary Dimethyl methylphosphonate" (PDF). ashland.com. Ashland Global. Retrieved April 27, 2022.
  5. ^ "Israel says El Al crash chemical 'non-toxic'". BBC. 2 October 1998. Archived from the original on 18 August 2003. Retrieved 2 July 2006.
  6. ^ Greenberg, Joel (2 October 1998). "Nerve-Gas Element Was in El Al Plane Lost in 1992 Crash". The New York Times. Retrieved 11 October 2007.
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