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Methylphosphonyl dichloride

Chemical compound From Wikipedia, the free encyclopedia

Methylphosphonyl dichloride
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Methylphosphonyl dichloride (DC) or dichloro is an organophosphorus compound. It has commercial application in oligonucleotide synthesis,[1] but is most notable as being a precursor to several chemical weapons agents. It is a white crystalline solid that melts slightly above room temperature.[2]

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Synthesis and reactions

Methylphosphonyl dichloride is produced by oxidation of methyldichlorophosphine, with sulfuryl chloride:[3]

CH3PCl2 + SO2Cl2 → CH3P(O)Cl2 + SOCl2

It can also be produced from a range of methylphosphonates (e.g. dimethyl methylphosphonate) via chlorination with thionyl chloride. Various amines catalyse this process.[4] With hydrogen fluoride or sodium fluoride, it can be used to produce methylphosphonyl difluoride. With alcohols, it converts to the dialkoxide:[5]

CH3P(O)Cl2 + 2 HOR → CH3P(O)(OR)2 +  HCl
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Safety

Methylphosphonyl dichloride is very toxic and reacts vigorously with water to release hydrochloric acid. It is also listed under Schedule 2 of the Chemical Weapons Convention as it is used in the production of organophosphorus nerve agents such as sarin and soman.

References

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