Synthesis of adamsite

Preparation of adamsite

Alternative Names: Adamsit; Diphenylaminechlorarsine; Phenazarsine chloride; 10-CHLORO-5,10-DIHYDROPHENARSAZINE; Diphenylaminechloroarsine;

Preparation of adamsite

Preparation of adamsite

42 g of diphenylamine and 21 ml hydrochloric acid (d=1.19) are placed in a porcelain dish of about 300 ml capacity and heated with constant stirring until all the water has been driven off. Diphenylamine hydrochloride is obtained as a white powder; it is dried for 2-3 hours at 50-60° C and it is mixed with 25 g of arsenious oxide and melted with continuous stirring. When the whole mixture is molten, the temperature is gradually raised; at 140° C the reaction becomes vigorous and water vapour is evolved. After 3-4 hours the temperature rises to 200° C and the evolution of water vapour ceases: the reaction may then be considered as complete. The product obtained is purified by crystallisation from xylene. Yield is almost theoretical.

The war gases chemistry and analysis, by M. Sartory, 320-321, 1939

IUPAC Name

10-chloro-5H-phenarsazinine

InChI

InChI=1S/C12H9AsClN/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8,15H

InChI Key

PBNSPNYJYOYWTA-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C(=C1)NC3=CC=CC=C3[As]2Cl

MeSH Synonyms

10-chloro-5,10-dihydroarsacridine, adamsite, diphenylaminochloroarsine, phenarsazine chloride

Depositor-Supplied Synonyms

Adamsite, Adamsit, Diphenylaminechlorarsine, Phenazarsine chloride, 10-CHLORO-5,10-DIHYDROPHENARSAZINE, Diphenylaminechloroarsine, Chloro diphenylaminearsine, Phenarsazine, 10-chloro-, Phenarsazine chloride, Phenarsazine chloride (ACN), 5-Aza-10-arsenaanthracene chloride, 10-Chloro-5,10-dihydroarsacridine, 578-94-9, Caswell No. 648, Diphenylamine chloroarsine, Fenarsazinchlorid [Czech], NSC 86138, 10-chloro-5H-phenarsazinine, Phenarsazine, 10-chloro-5,10-dihydro-, EINECS 209-433-1, UN1698, EPA Pesticide Chemical Code 063901, BRN 0178698, Fenarsazinchlorid, CHLOROPHENARSAZENE, Phenarsazine,10-dihydro-, AC1L1X6Y, DM [Chemical Warfare Agent], SCHEMBL290774, UNII-QI287G628L, HSDB 7599, PBNSPNYJYOYWTA-UHFFFAOYSA-N, QI287G628L, NSC86138, 6079AF, NSC-86138, UN 1698, WLN: T C666 B-AS- IMJ BG, HE004166, PL060288, LS-102983, 10-CHLORO-5,10-DIHYDROPHENARSAZININE, Diphenylamine chloroarsine [UN1698] [Poison], Diphenylamine chloroarsine [UN1698] [Poison], 4-27-00-09796 (Beilstein Handbook Reference)

Removed Synonyms

Diphenylaminochloroarsine, CID11362, DM

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