Phenyl Carbylamine Chloride

This substance was prepared in 1874 by Sell and Zierold, and was employed as a war gas towards the middle of 1917 (in May) by the Germans. It was principally used in projectiles together 

Phenyl carbylamine chloride is usually prepared by the chlorination of phenyl isothiocyanate  

Various methods have been employed for preparing phenyl isothiocyanate. It may be obtained, for instance, from carbon disulphide and aniline, which react to form thiocarbanilide in presence of alkali hydroxides  

Another rather similar method is to treat carbon disulphide with aniline in presence of lime. Calcium phenyl dithiocarbamate is first formed, according to the equation  

On treating this with an alkaline zinc chloride solution it decomposes with production of phenyl isothiocyanate  

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Phenyl Carbylamine Chloride Phenyl Dibromoarsine Phenyl Dichloroarsine Phenyl Mercury Acetate Phenylaceyl Chloride Phenylarsenic Dichloride Phenylarsonous Dichloride Phenylcarbamine Phenylcarbonimidic Dichloride Phenylchloromethylketone Phenylisocyanide Dichloride Phenylisonitrile Dichloride Phenylmethylaminpropane Philippine Downy Mildew Phix... 

N-piCHLOROMETHYLENE)ANILINE PHENYL-CARBONIMIDIC DICHLORIDE N-PHEN XCARBO-NIiMIDIC DICHLORIDE PHENYL CARBYLAMINE CHLORIDE PHENYLCARBYLAMINE CHLORIDE POTI PHENYLIMIDOCARBONYL CHLORIDE N-PHENYLIMIDOPHOSGENE PHENYLIMINO-CARBONYL DICHLORIDE N-PHENYLIMINO-CARBONYL DICHLORIDE PHENYLISONITRILE DICHLORIDE... 

IV CjHs—CHaBr Benzyl bromide /CH,C1 Chloroacetophenone CeHsN = CCI2 Phenyl carbylamine chloride (CeHj)2AsCl Dig nyl chlwyEtrsine... 

Among the various compounds containing the CN group which were employed in the war of 1914-18, hydrocyanic acid, phenyl carbylamine chloride and the cyanogen halides, particularly cyanogen bromide, were most widely used. 

Phenyl carbylamine chloride is an oily liquid which is only slightly volatile. It is pale yellow in colour and has an onion-like odour. At ordinary pressure it boils at 208° to 210° C., and at 15 mm. pressure at 95° C. The specific gravity is 1-30 at 15° C., and the vapour density is 6 03. The coefficient of thermal expansion is 0 000895. The volatility at 20° C. is 2,100 mgm. per cu. m. It is insoluble in water, but soluble in chloroform, carbon tetrachloride and other organic solvents. 

Phenyl carbylamine chloride, even when diffused in the air in the vapour state (at concentrations above 4%), produces with the Grignard reagent (see p. 248) a turbidity like that obtained with dichloroethyl sulphide (Hanslian). 

The irritant power of phenyl carbylamine chloride is very great according to Muller 3 mgm. are sufficient to produce irritation. The limit of insupportability is 30 mgm. per cu. m. of air. The mortality-product is 3,000 according to Muller and 5,000 for 10 minutes exposure according to Prentiss. 

It has been found that while the aliphatic arsines and phenyl carbylamine chloride produce a similar turbidity at high concentration (4%), other substances such as mono-, di- and tri-chloromethyl chloroformates, chloropicrin, benzyl bromide, acrolein, the aromatic arsines, thiodiglycol, etc., do not react. 

Phenyl carbylamine chloride Phenyldichloroarsine Dichloromethyl ether Ethyldichloroarsine Phenyldibromoarsine Dibromomethyl ether... 

Phenyl carbylamine chloride Phenylimidocarbonyl chloride ( ) incapacitant Reagent War gas... 

Molybdenum fluoride Nickel carbonyl Nitrogen peroxide Nitrogen trifluoride N itro some thy lure thane Oleum (fuming sulfuric acid) Oxygen difluoride Paranitro benzyl chloride Perchloromethyhnercaptan Phenylbromoacetonitrile Phenyl-carbylamine chloride Phenylimidophosgene Phosphine... 

Carboxylic acids, a-bromination of 55, 31 CARBOXYLIC ACID CHLORIDES, ketones from, 55, 122 CARBYLAMINE REACTION, 55, 96 Ceric ammonium nitrate [Ammonium hexa mtrocerate(IV)[, 55, 43 Chlorine, 55, 33, 35, 63 CHROMIUM TRIOXIDE-PYRIDINE COMPLEX, preparation in situ, 55, 84 Cinnamomtnle, a-phenyl- [2-Propeneni-tnle 2,3-diphenyl-], 55, 92 Copper(l) iodide, 55, 105, 123, 124 Copper thiophenoxide [Benzenethiol, copper(I) salt], 55, 123 CYCLIZATION, free radical, 55, 57 CYCLOBUTADIENE, 55, 43 Cyclobutadieneiron tricarbonyl [Iron, tn-carbonyl(r)4-l,3-cyclo-butadiene)-], 55,43... 

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