Synthesis of diphenylchloroarsine (sneezing gas)

Preparation of diphenylchloroarsine

Preparation of diphenylchloroarsine (sneezing gas)

Preparation of diphenylchloroarsine (sneezing gas)

57 g sodium cut into slices are placed in a round-bottomed flask fitted with a reflux condenser and covered with 300 ml benzene containing 1-2% ethyl acetate (which catalyzes the reaction). After allowing this mixture to stand for 30 minutes (in order to activate the sodium metal) 136 g chlorobenzene and 85% arsenic chloride are slowly added. After a few minutes the reaction is considerably accelerated, and if necessary the flask should be cooled externally with a freezing mixture. It is then allowed to remain in the freezing mixture for 12 hours, being agitated during the first 2-3 hours. The solution is then filtered, the precipitate washed with hot benzene and the combined wash-liquid and filtrate distilled until the thermometer reaches 200° C. A yellow oil remains, consisting of triphenyl arsine, and, on cooling, this solidifies. 30 g of the triphenyl arsine obtained are weighed into a wide-mouthed vessel and heated to 350° C to 360° C while 25.5 ml arsenic trichloride are introduced drop by drop from a tap-funnel with a capillary outlet. Diphenyl chlororarsine is distilled in vacuo yielding a dark brown product. When pure, diphenyl chloroarsine forms colourless crystals which melt at 41° C.

The war gases chemistry and analysis,by M. Sartory, 303-304, 1939

IUPAC Name

chloro(diphenyl)arsane

InChI

InChI=1S/C12H10AsCl/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H

InChI Key

YHHKGKCOLGRKKB-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)[As](C2=CC=CC=C2)Cl

MeSH Synonyms

Clark 1, diphenyl arsine chloride

Depositor-Supplied Synonyms

Sneezing gas, Diphenylchlorarsine, Blue cross, Clark I, Chlorodiphenylarsine, DIPHENYLCHLOROARSINE, Clark 1, Arsinous chloride, diphenyl-, Arsine, chlorodiphenyl, Difenylchlorarsin, Chlor-difenylarsin, Diphenylchloorarsine, Diphenyl chloroarsine, Diphenylarsinous chloride, Difenylchlorarsin [Czech], 712-48-1, Chlor-difenylarsin [Czech], Diphenylchloorarsine [Dutch], EINECS 211-921-4, Diphenylchloroarsine, liquid or solid, UN1699, BRN 2937168, chloro(diphenyl)arsane, Diphenylarsenic chloride, AC1Q3FJI, Diphenylchloroarsine, solid, Diphenylarsinous chloride #, Diphenylchloroarsine, liquid, AC1L20GP, SCHEMBL2028533, UNII-1H39V3559B, CTK5D3763, YHHKGKCOLGRKKB-UHFFFAOYSA-N, Arsinous chloride,As,As-diphenyl-, Arsinous chloride, diphenyl- (9CI), 1H39V3559B, UN 1699, LS-21806, Diphenylchloroarsine, liquid [UN1699] [Poison], Diphenylchloroarsine, solid [UN1699] [Poison], 3-16-00-00944 (Beilstein Handbook Reference), Diphenylchloroarsine, liquid [UN1699] [Poison], Diphenylchloroarsine, solid [UN1699] [Poison]

Removed Synonyms

CID12836, DA

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