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Diphenylchlorarsine

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Diphenylchlorarsine
Names
IUPAC name diphenylchloroarsenic, chlorodiphenylarsane, sneezing gas
Other names diphenylchlorarsine
Identifiers
CAS Number
3D model (JSmol)
Abbreviations Ph2AsCl
ChemSpider
ECHA InfoCard 100.010.839 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H10AsCl/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10HKey: YHHKGKCOLGRKKB-UHFFFAOYSA-N
  • InChI=1/C12H10AsCl/c14/h1-10H
  • InChI=1/C12H10AsCl/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10HKey: YHHKGKCOLGRKKB-UHFFFAOYAA
SMILES
  • Cl(C1=CC=CC=C1)C2=CC=CC=C2
  • Cl(c1ccccc1)c2ccccc2
Properties
Chemical formula C12H10AsCl
Molar mass 264.59 g mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Diphenylchloroarsine (DA) is the organoarsenic compound with the formula (C6H5)2AsCl. This odorless, toxic liquid was once used as harassing agent. It is also an intermediate in the preparation of other organoarsenic compounds. The molecule consists of a pyramidal As(III) center attached to two phenyl rings and one chloride.

Uses

Diphenylchlorarsine was first used as a chemical weapon on the Western front during the trench warfare of World War I It belongs to the class of chemicals classified as vomiting agents. Other such agents are diphenylcyanoarsine (DC) and diphenylaminechlorarsine (DM, adamsite).

It is a useful reagent in the preparation of other diphenylarsenic compounds, e.g. by reactions with Grignard reagents:

RMgBr + (C6H5)2AsCl → (C6H5)2AsR + MgBrCl
(R = alkyl, aryl)

Safety

Diphenylchlorarsine is known to cause sneezing, coughing, headache, salivation, and vomiting. China and Japan are negotiating remediation of stocks of a variety of organoarsenic weapons stored in northeastern China including chlorodiphenylarsine.

References

  1. Gilbert, Martin (1995). First World War. HarperCollins. ISBN 0006376665.
  2. Christopher P Holstege, Jennifer S Boyle (Nov 26, 2008). "CBRNE - Vomiting Agents - Dm, Da, Dc".
  3. "Abandoned Chemical Weapons (ACW) in China". 02/06/2004. {{cite web}}: Check date values in: |date= (help)
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