Phenarsazines

Phenanthro[l,2-d][l,2,3]selenadiazole, 10,11 dihydro- H NMR, 6, 348 synthesis, 6, 353 Phenanthro[b]thiophenes synthesis, 4, 914 Phenanthro[4,5-bcd]thiophenes synthesis, 4, 883, 907, 914 Phenanthro[9,10-ej[l, 2,4]triazines synthesis, 3, 434 Phenarsazin synthesis, 1, 561 Phenazine dyes, 3, 196-197 nitration, 3, 177 UV Spectra, 2, 127 Phenazine, 3-amino-2-hydroxy-in colour photography, 1, 374 Phenazine, 1-chloro-nucleophilic substitution, 3, 164-165 5-oxide... 

DM Adamsite, Phenarsazine chloride, Diphenylaminechloroarsine,10-chloro-5,10- dihydrophenarsazine... 

Diphenylamine chlorarsine (arsenical gas, also known as Adamsite (phenarsazine chloride))... 

DIPHENYLAMINECHLORARSINE (ADAMSITE) (DIPHEN-YLAMINEARSINE CHLORIDE) (PHENARSAZINE CHLORIDE)... 

S-Aza-10-arsenaa nthracene chloride 10-Ch loro-5,10-dihydroarsacridine 10-Chloro-5,10-dihydrophenarsazine Dibenzo-1 -ch loro-1,4-arsen Ine Dl phenylaminochloroarsine Phenarsazine chloride... 

Various other compounds containing the CN— radicle were studied towards the end of the war and since that period. Of these, chlorobenzyl cyanide, bromobenzyl cyanide, diphenyl cyanoarsine, phenarsazine cyanide, etc., were used to a considerable extent as war gases. Recently cyanogen fluoride has also been prepared and studied. It is a colourless gas with powerful lachrymatory properties. 

Most of the aliphatic and aromatic arsines employed during the war of 1914-18 were substances which had been known for some time. The only new substances are the chlorovinyl arsines and phenarsazine chloride, of whose practical efficiency somewhat conflicting opinions are still held. 

Diphenylcmine. Chlorovinyl dichloroarsine reacts on heating with diphenylamine to form 10 chloro 5 10 dihydro phenarsazine ... 

With diphenylamine, 10 chloro 510 dihydro phenarsazine is formed ... 

In order to attain the degree of subdivision of diphenyl chloroarsine, diphenyl cyanoarsine or phenarsazine chloride which has been mentioned above, it is first necessary to volatilise the substance by some method and then to allow the vapour to condense in the air. This is carried out by means of the so-called irritant candles. ... 

Various analogous and homologous compounds of phenarsazine chloride have been studied. Among the more important may be mentioned phenarsazine bromide, obtained by the action of arsenic bromide on diphenylamine, phenarsazine iodide and phenarsazine fluoride, as well as phenarsazine cyanide A All these compounds have toxic properties similar to those of phenarsazine chloride. ... 

Substances of analogous types to that of the phenarsazine derivatives have also been prepared. Lewis first, and later Turner prepared phenoxarsine chloride (6 chlorophenoxarsine) ... 

These substances, which are very similar in properties to phenarsazine chloride, have the drawback that their preparation is iti each case very laborious. 

Wieland obtained phenarsazine chloride by treating diphenyl-amine with arsenic chloride ... 

American Method. The process used by the Americans at Edgewood Arsenal for the manufacture of phenarsazine chloride is based on the reaction of diphenylamine with arsenic chloride ... 

In order to prepare phenarsazine chloride by this method it is sufficient to mix diphenylamine hydrochloride with arsenious oxide and heat to 130° C. After the mixture is melted, the temperature is gradually raised to 200° C. When the evolution of water ceases, the reaction is complete. Yield 95% of the theoretical.. 

Fig. 18 shows a diagram of the plant proposed by Professor Contardi for the industrial preparation of phenarsazine chloride. 

With a battery of four kettles of this description, it is possible to make 6 tons of phenarsazine chloride by this method in 24 hours. 

Phenarsazine chloride in the crude state is a crystalline solid, dark green or sometimes brown in colour. It may be obtained in the pure condition by crystallisation, or, better, by vacuum sublimation. It is then of a canary-yellow colour with a melting... 

Water. Phenarsazine chloride, unlike the arsenic compounds previously described, is slowly hydrolysed by water. On adding a little water to the alcoholic solution, a turbidity appears which consists of phenarsazine oxide. ... 

Bromine. By the action of bromine on phenarsazine chloride in acetic acid solution, a brominated derivative is not obtained. 

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