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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]
Methyldichlorophosphine is produced by alkylation of phosphorus trichloride with methyl iodide followed by reduction of the resulting phosphonium salt with iron powder: [2] [3]
For example, methyl iodide catalyses the conversion of trimethylphosphite to the phosphonate ester dimethyl methylphosphonate: P(OMe) 3 → MePO(OMe) 2 These esters can be hydrolysed to the acid (Me = methyl):
[2] [3] This reaction is widely used for the synthesis of various phosphonates, phosphinates, and phosphine oxides. Several reviews have been published. [4] [5] The reaction also occurs for coordinated phosphite ligands, as illustrated by the demethylation of {(C 5 H 5)Co[(CH 3 O) 3 P] 3} 2+ to give {(C 5 H 5)Co[(CH 3 O) 2 PO] 3} −, which is ...
Methylphosphonic acid is an organophosphorus compound with the chemical formula CH 3 P(O)(OH) 2. The phosphorus center is tetrahedral and is bonded to a methyl group, two OH groups and an oxygen. Methylphosphonic acid is a white, non-volatile solid that is poorly soluble in organic solvent but soluble in water and common alcohols.
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.
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The compound is an intermediate for the synthesis of other chemicals for instance dimethylphenylphosphine: C 6 H 5 PCl 2 + 2 CH 3 MgI → C 6 H 5 P(CH 3) 2 + 2 MgICl. Many tertiary phosphines can be prepared by this route. [3] In the McCormack reaction dichlorophenylphosphine adds dienes to give the chlorophospholenium ring. [4]