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Methyldichlorophosphine

From Wikipedia, the free encyclopedia
Methyldichlorophosphine
Names
Preferred IUPAC name
Methylphosphonous dichloride
Other names
Methyl phosphonous dichloride, Dichloromethylphosphine, SW[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.010.575Edit this at Wikidata
EC Number
  • 211-631-8
UN number2845
  • InChI=1S/CH3Cl2P/c1-4(2)3/h1H3
    Key: CDPKWOKGVUHZFR-UHFFFAOYSA-N
  • CP(Cl)Cl
Properties
CH3Cl2P
Molar mass116.91 g·mol−1
AppearanceColorless liquid
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Methyldichlorophosphine (alternatively known asdichloro(methyl)phosphane, SW andmethylphosphonous dichloride) is anorganophosphorus compound with the chemical formula CH3PCl2. It is a colorless, corrosive, flammable, and highly reactive liquid with a pungent odor.

Preparation

[edit]

Methyldichlorophosphine is produced by alkylation ofphosphorus trichloride withmethyl iodide followed by reduction of the resulting phosphonium salt with iron powder:[2][3]

CH3I + PCl3 + AlCl3 → [CH3PCl3]+AlCl3I
[CH3PCl3]+AlCl3I + Fe → CH3PCl2 + FeICl + AlCl3

The compound is an intermediate for the synthesis of other chemicals for instancedimethylphenylphosphine.

Uses

[edit]

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 herbicideGlufosinate. It is also used in the production offlameproofing compounds.[4]

Due to the recycling problem ofphosphoryl chloride, SW was adopted in step three of theDMHP process in the preparation ofSarin.[5] SW was also adopted as a standard precursor to V agents, having been used to prepareQL for unitary and binaryVX. SW was the first agent adopted to prepare VX in one pot reaction by aqueous medium.[6]

Safety

[edit]

It is also toxic if inhaled, can cause burns upon contact with the skin and eyes, and releases fumes ofhydrochloric acid in moist environments.[7]

References

[edit]
  1. ^"Infrared Spectroscopic Observations on the Fate of Organophosphorus Compounds Exposed to Atmospheric Moisture. Part I. G-Agents and Related Compounds"(PDF).
  2. ^Robert Engel; JaimeLee Iolani Cohen (2004).Synthesis of Carbon–Phosphorus Bonds. CRC.ISBN 0-8493-1617-0.
  3. ^Mirosław S (1977), "A Simple Preparation of Methylphosphonous Dichloride",Synthesis,1977 (7): 450,doi:10.1055/s-1977-24435
  4. ^Svara, Jürgen; Weferling, Norbert; Hofmann, Thomas (2007), "Phosphorus Compounds, Organic",Ullmann's Encyclopedia of Industrial Chemistry (7th ed.),doi:10.1002/14356007.a19_545.pub2,ISBN 978-3-527-30385-4
  5. ^Sass, S; Morgan, C. U. Chlorination End-Point Indication by Conductivity and Color Change (Step III, DMHP Process). Formal rept.
  6. ^cit-OPDC. The preparatory manual to chemical warfare. Vol 1: V agents: X
  7. ^Pubchem."Dichloro(methyl)phosphane".pubchem.ncbi.nlm.nih.gov. Retrieved19 April 2018.
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