2-Bromobenzyl cyanide

Bromobenzyl cyanide was prepared by Reimer in 1881, but it was not isolated in the pure state until 1914. It was employed as a war gas by the French in the last years of the war, usually in solution in chloropicrin. 

According to American experiments made since the war, this compound is to be considered as one of the most efficient of the war gases because of its great persistence and its high lachrymatory power. 

It is also known as Camite (France), and by the symbol CA (America). 

Bromobenzyl cyanide was prepared by Reimer by the action of bromine on benzyl cyanide heated to 120° to 130° C. 

This compound may be prepared either by the action of cyanogen bromide on an alcoholic solution of benzyl cyanide in presence of sodium ethylate, according to the equation  

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Initialiy, 4-bromobenzyl-cyanide is reacted with sodium amide and 2-chloropyridine to give bromophenyl-pyridyl acetonitrile. This is then reacted with sodium amide then dimethyi amino ethyl chloride to give 4.bromophenyl-dimethylamlnoethyl-pyrldyi acetonitrlie. This intermediate is then hydrolyzed and decarboxylated to bromphenirame using 80% H2SO4 at 140°-150°C for 24 hours. The brompheniramine maieate may be made by reaction with maleic acid in ethanol followed by recrystallization from pentanoi. 

Clorazepate dIpotassium Cycrimine HCI Diphemanil methyl sulfate Feno profen Medazepam Procyclidine HCI Tamoxifen Tiemonium iodide 4-Bromobenzyl cyanide... 

Brombenzyl cyanide (CA)—also called a-bromobenzyl cyanide, o-bromotolunltrlle, bromobenzylnitrlle, and a-bromophenylaceto-nitrile--was the most powerful lacrlmator used In World War I (see Table 4-1). It was Introduced by the French army and adopted as the standard U.S. lacrlmator In 1918. It was temporarily abandoned because of its reactions with metal and instability in storage.3 10 Interest in it revived when a need arose for a chemical that was more persistent than CS and CN in enclosed areas, such as rooms and earthen tunnels. In this connection, vapors of CA from ground contamination are lacrlmatory for 15-30 d.6... 

Bromoacetone [598-31-2], C3H5BrO, a-bromobenzyl cyanide [5798-79-8], CgH6BrN, m-xylyl bromide [620-13-3], CgH9Br, < -xylyl bromide [89-92-9], CgH9Br, and/-xylyl bromide [104-81-4], CgH9Br, are used in war-gas formulations (see Chemicals in war). 5-Bromouracil [51-20-7], C4H3BrN202, is used experimentally as a mutagen. 

Bromoanisoles, b301, b302, b303 p-Bromobenzenethiol, b354 4-Bromobenzyl cyanide, b329... 

Bromobenzyl cyanide (CA) 1881 (Riener/ Insoluble in water Soluble in organic solutions 0.12 4.0 Immediate 0.8 30 1,100... 

SYNS BBC BBN BROMBENZYL CYANIDE a-BROMOBENZYL CYANIDE a-BROMOBENZYL-NITRILE a-BROMOPHENYLACETONITRILE a-BROMO-a-TOLUNTTRILE CA CAMITE... 

BROMOBENZYLCYANIDE see BNW50 p-BROMOBENZYL CYANIDE see BNV750 a-BROMOBENZYL CYANIDE see BMW250 BROMOBENZYLNITRILE see BMW250 a-BROMOBENZYLNITRILE see BMW250... 

It is seen from this table that the variation in the vapour tensions of the war gases is very great. For example, some of these substances have a vapour tension greater than one atmosphere (phosgene, cyanogen chloride), while others (dichloroethyl sulphide, bromobenzyl cyanide) have an extremely low vapour tension, and for this reason special methods are necessary in order to obtain efficient results in using them in warfare. 

The last requisite of a war gas is comparatively important the absence of any attack on the material in which it is to be stored or used. Some war gases strongly attack the iron which commonly forms the storage containers and projectiles such are xylyl bromide, the incompletely chlorinated formates, bromobenzyl cyanide and a few others. 

Includes Hydrocyanic acid Cyanogen chloride Bromobenzyl cyanide. ... 

A study of those compounds in which the CN-group is in the side chain containing the halogen atom has indicated that chlorobenzyl cyanide, and bromobenzyl cyanide to an even greater degree, have an increased lachrymatory power. These compounds are described in the chapter on Cyanogen Compounds (see p. 196). 

Benzyl chloride was prepared in 1853 by Cannizzaro by acting on benzyl alcohol with hydrochloric acid. It is particularly well known for its use in organic synthesis. It was used as a war gas in the war of 1914-18, but only for a short time. To-day its importance is as a raw material for the preparation of bromobenzyl cyanide. 

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. 

I, 000 c.p. Osram lamp. By this method a much higher yield of bromobenzyl cyanide is obtained. ... 

In the industrial manufacture of bromobenzyl cyanide it is preferable to commence with benzyl chloride rather than benzyl bromide. This is easily obtained by the chlorination of toluene under the influence of sunlight (see p. 129) or by the aid of a mercury vapour lamp. ... 

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