Methyldichlorophosphine

Methyldichlorophosphine (alternatively known as dichloro(methyl)phosphane and methyl phosphonous dichloride) is an organophosphorus compound with the chemical formula CH3PCl2. It is a colorless, corrosive, flammable, and highly reactive liquid with a pungent odor.

Methyldichlorophosphine
Names
Preferred IUPAC name
Methylphosphonous dichloride
Other names
Methyl phosphonous dichloride, Dichloromethylphosphine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.575
EC Number
  • 211-631-8
UN number 2845
  • InChI=1S/CH3Cl2P/c1-4(2)3/h1H3
    Key: CDPKWOKGVUHZFR-UHFFFAOYSA-N
  • CP(Cl)Cl
Properties
CH3Cl2P
Molar mass 116.91 g·mol−1
Appearance Colorless liquid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation

Methyldichlorophosphine is produced by alkylation of phosphorus trichloride with methyl iodide followed by reduction of the resulting phosphonium salt with iron powder:[1] The compound is an intermediate for the synthesis of other chemicals for instance dimethylphenylphosphine:

CH3I + PCl3 + AlCl3 → [CH3PCl3]+AlCl3I−
[CH3PCl3]+AlCl3I− + Fe → CH3PCl2 + FeClI + AlCl3

Uses

Methyldichlorophosphine belongs to the group of halophosphines, some of which are used as intermediates in the production of plant protection agents, stabilizers for plastics, and catalysts. It is a precursor of the herbicide Glufosinate. It is also used in the production of flameproofing compounds.[2]

Due to the recycling problem of phosphoryl chloride, SW was adopted in step three of the DMHP process in the preparation of GB.[3] SW was also adopted as a standard precursor to V agents, having been used to prepare QL for unitary and binary VX. SW was the first agent adopted to prepare VX in one pot reaction by aqueous medium.[4]

Safety

It is also toxic if inhaled, can cause burns upon contact with the skin and eyes, and releases fumes of hydrochloric acid in moist environments.[5]

References
  1. Robert Engel; JaimeLee Iolani Cohen (2004). Synthesis of Carbon–Phosphorus Bonds. CRC. ISBN 0-8493-1617-0.
  2. "Phosphorus Compounds, Organic", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), 2007, doi:10.1002/14356007.a19_545.pub2
  3. Sass, S; Morgan, C. U. Chlorination End-Point Indication by Conductivity and Color Change (Step III, DMHP Process). Formal rept.
  4. cit-OPDC. The preparatory manual to chemical warfare. Vol 1: V agents: X
  5. Pubchem. "Dichloro(methyl)phosphane". pubchem.ncbi.nlm.nih.gov. Retrieved 19 April 2018.
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