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Dimethyl methylphosphonate

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.

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
  • 756-79-6 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL2924224
ChemSpider
  • 12418 Y
ECHA InfoCard 100.010.957
EC Number
  • 212-052-3
  • 12958
UNII
  • 20Z996230U Y
UN number 1993
  • DTXSID0020494
  • 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
  • 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:
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).
Y verify (what is YN ?)

Synthesis edit

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

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.[3] It can be used as a sarin-simulant for the calibration of organophosphorus detectors.

Uses edit

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.[4] 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).[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 edit

  1. ^ "GESTIS-Stoffdatenbank". gestis.dguv.de.
  2. ^ Jasiak, Aleksandra; Mielniczak, Grażyna; Owsianik, Krzysztof; Koprowski, Marek; Krasowska, Dorota; Drabowicz, Józef (2019). "Solvent-Free Michaelis–Arbuzov Rearrangement under Flow Conditions". The Journal of Organic Chemistry. 84 (5): 2619–2625. doi:10.1021/acs.joc.8b03053. PMID 30698971. S2CID 73412537.
  3. ^ 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. doi:10.1080/10426509008038002.
  4. ^ "Product Stewardship Summary Dimethyl methylphosphonate" (PDF). ashland.com. Ashland Global. Retrieved April 27, 2022.
  5. ^ . 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.

dimethyl, methylphosphonate, organophosphorus, compound, with, chemical, formula, ch3po, och3, colourless, liquid, which, primarily, used, flame, retardant, names, preferred, iupac, name, other, names, methylphosphonic, acid, dimethyl, esterdimethoxymethyl, ph. 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 Dimethyl methylphosphonate Names Preferred IUPAC name Dimethyl methylphosphonate Other names methylphosphonic acid dimethyl esterdimethoxymethyl phosphine oxidedimethyl methanephosphonatedimethyl methyl phosphonateFran TF 2000Fyron DMMPMetaranNSC 62240O O dimethyl methylphosphonate methoxy methyl phosphoryl oxy methaneReoflam DMMP Identifiers CAS Number 756 79 6 Y 3D model JSmol Interactive image ChEMBL ChEMBL2924224 ChemSpider 12418 Y ECHA InfoCard 100 010 957 EC Number 212 052 3 PubChem CID 12958 UNII 20Z996230U Y UN number 1993 CompTox Dashboard EPA DTXSID0020494 InChI InChI 1S C3H9O3P c1 5 7 3 4 6 2 h1 3H3 YKey VONWDASPFIQPDY UHFFFAOYSA N YInChI 1 C3H9O3P c1 5 7 3 4 6 2 h1 3H3Key VONWDASPFIQPDY UHFFFAOYAG SMILES O P OC OC C Properties Chemical formula C 3H 9O 3P 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 Solubility in water slowly hydrolyses Hazards 1 Occupational safety and health OHS OSH Main hazards Toxic GHS labelling Pictograms Signal word Warning Hazard statements H319 H340 H361f Precautionary statements P201 P305 P351 P338 P308 P310 Flash point 69 C 156 F 342 K closed cup Lethal dose or concentration LD LC LD50 median dose Oral rat 8 210 mg kgInhalation rat 1h 20 13 mg LDermal rabbit gt 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 verify what is Y N Infobox referencesSynthesis editDimethyl methylphosphonate can be prepared from trimethyl phosphite and a halomethane e g iodomethane via the Michaelis Arbuzov reaction 2 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 3 It can be used as a sarin simulant for the calibration of organophosphorus detectors Uses editThe 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 4 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 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 edit GESTIS Stoffdatenbank gestis dguv de Jasiak Aleksandra Mielniczak Grazyna Owsianik Krzysztof Koprowski Marek Krasowska Dorota Drabowicz Jozef 2019 Solvent Free Michaelis Arbuzov Rearrangement under Flow Conditions The Journal of Organic Chemistry 84 5 2619 2625 doi 10 1021 acs joc 8b03053 PMID 30698971 S2CID 73412537 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 doi 10 1080 10426509008038002 Product Stewardship Summary Dimethyl methylphosphonate PDF ashland com Ashland Global Retrieved April 27 2022 Israel says El Al crash chemical non toxic BBC 2 October 1998 Archived from the original on 18 August 2003 Retrieved 2 July 2006 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 Retrieved from https en wikipedia org w index php title Dimethyl methylphosphonate amp oldid 1177302802, wikipedia, wiki, book, books, library,

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