dimethyl methylphosphonate
{{short description|Chemical compound}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 402318814
| ImageFile1 =Dimethyl methylphosphonate.svg
| ImageSize1 =150px
| ImageFile2 =Dimethyl-methylphosphonate-3D-balls.png
| ImageCaption = Ball-and-stick model of dimethyl methylphosphonate
| ImageSize2 =150px
| PIN =Dimethyl methylphosphonate
| OtherNames ={{Unbulleted list|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}}
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =756-79-6
| ChEMBL = 2924224
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 12418
| EC_number = 212-052-3
| PubChem =12958
| UNNumber = 1993
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 20Z996230U
| InChI = 1/C3H9O3P/c1-5-7(3,4)6-2/h1-3H3
| InChIKey = VONWDASPFIQPDY-UHFFFAOYAG
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H9O3P/c1-5-7(3,4)6-2/h1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VONWDASPFIQPDY-UHFFFAOYSA-N
| SMILES = O=P(OC)(OC)C
}}nncjjfjx
|Section2={{Chembox Properties
| C=3 | H=9 | O=3 | P=1
| Appearance =colourless liquid
| Density =1.145 g/mL at 25 °C
| MeltingPtC =-50
| BoilingPtC =181
| Solubility =slowly hydrolyses
}}
|Section3={{Chembox Hazards
| MainHazards =Toxic
| Hazards_ref = {{cite web |title=GESTIS-Stoffdatenbank |url=https://gestis.dguv.de/data?name=026580 |website=gestis.dguv.de}}
| GHSPictograms = {{GHS07}}{{GHS08}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|319|340|361f}}
| PPhrases = {{P-phrases|201|305+351+338|308+310}}
| FlashPtC = 69
| FlashPt_notes = closed cup
| AutoignitionPt =
| LD50 = {{Unbulleted list|Oral (rat) 8,210 mg/kg|Inhalation (rat) 1h 20.13 mg/L|Dermal (rabbit) >2,000 mg/kg}}
}}
}}
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.{{cite journal |doi=10.1021/acs.joc.8b03053|title=Solvent-Free Michaelis–Arbuzov Rearrangement under Flow Conditions|year=2019|last1=Jasiak|first1=Aleksandra|last2=Mielniczak|first2=Grażyna|last3=Owsianik|first3=Krzysztof|last4=Koprowski|first4=Marek|last5=Krasowska|first5=Dorota|last6=Drabowicz|first6=Józef|journal=The Journal of Organic Chemistry|volume=84|issue=5|pages=2619–2625|pmid=30698971|s2cid=73412537}}
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.{{cite journal|last=Maier|first=Ludwig|title=Organic Phosphorus Compounds 90.l A Convenient, One-Step Synthesis of Alkyl- and Arylphosphonyl Dichlorides|journal=Phosphorus, Sulfur, and Silicon and the Related Elements|year=1990|volume=47|issue=3–4|pages=465–470|doi=10.1080/10426509008038002}} 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.{{Cite web |title=Product Stewardship Summary Dimethyl methylphosphonate |url=https://www.ashland.com/file_source/Ashland/Documents/Sustainability/rc_dimethyl_methylphosphonate_pss.pdf |access-date=April 27, 2022 |website=ashland.com |publisher=Ashland Global}} 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 {{convert|100|and|1000|ST|t|sp=us}}.{{Citation needed|date=April 2008}}
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.{{Cite news |date=2 October 1998 |title=Israel says El Al crash chemical 'non-toxic' |publisher=BBC |url=http://news.bbc.co.uk/2/hi/europe/185199.stm |access-date=2 July 2006 |archive-url=https://web.archive.org/web/20030818042548/http://news.bbc.co.uk/2/hi/europe/185199.stm |archive-date=18 August 2003}}{{Cite news |last=Greenberg |first=Joel |date=2 October 1998 |title=Nerve-Gas Element Was in El Al Plane Lost in 1992 Crash |work=The New York Times |url=https://query.nytimes.com/gst/fullpage.html?res=9E04E5D91538F931A35753C1A96E958260&pagewanted=all |access-date=11 October 2007}}
References
{{reflist}}
{{Chemical agents}}
{{Motor fuel}}