Methylphosphonyl dichloride

Last updated
Methylphosphonyl dichloride
Methylphosphonic dichloride-2D-by-AHRLS-2012.png
Methylphosphonic-dichloride-3D-balls-by-AHRLS-2012.png
Names
Preferred IUPAC name
Methylphosphonic dichloride
Other names
Methanephosphonic dichloride
Methanephosphonic acid dichloride
Methylphosphonyl dichloride
Dichloro
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.578 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-634-4
PubChem CID
UN number 9206
  • InChI=1S/CH3Cl2OP/c1-5(2,3)4/h1H3
    Key: SCLFRABIDYGTAZ-UHFFFAOYSA-N
  • InChI=1/CH3Cl2OP/c1-5(2,3)4/h1H3
    Key: SCLFRABIDYGTAZ-UHFFFAOYAS
  • CP(=O)(Cl)Cl
Properties
CH3Cl2OP
Molar mass 132.91 g·mol−1
AppearanceWhite crystalline solid
Density 1.468 g/mL at 20 °C
Melting point 28 to 34 °C (82 to 93 °F; 301 to 307 K)
Boiling point 163 °C (325 °F; 436 K)
Reacts with water
Solubility Ether, THF
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Very toxic, reacts with water
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg
Danger
H314, H330
P260, P264, P271, P280, P284, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P320, P321, P363, P403+P233, P405, P501
Flash point >110 °C
Lethal dose or concentration (LD, LC):
26 ppm/4h by inhalation (rat)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methylphosphonyl dichloride (DC) or dichloro is an organophosphorus compound. It has a number of commercial uses[ vague ] 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. [1]

Contents

Synthesis and reactions

Methylphosphonyl dichloride is produced by oxidation of methyldichlorophosphine, with sulfuryl chloride: [2]

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. [3] With hydrogen fluoride or sodium fluoride, it can be used to produce methylphosphonyl difluoride. With alcohols, it converts to the dialkoxide: [4]

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

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.

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References

  1. "SAFETY DATA SHEET Methylphosphonic dichloride". SAFETY DATA SHEET Methylphosphonic dichloride. MilliporeSigma. June 26, 2020. Retrieved April 27, 2022.
  2. Svara, J.; Weferling, N.; Hofmann, T. "Phosphorus Compounds, Organic," In 'Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2008. doi : 10.1002/14356007.a19_545.pub2.
  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. Carl Patois, Philippe Savignac, Elie About-Jaudet, Noël Collignon (1996). "Bis(Trifluoroethyl) (carboethoxymethyl)phosphonate". Organic Syntheses. 73: 152. doi:10.15227/orgsyn.073.0152.{{cite journal}}: CS1 maint: multiple names: authors list (link)