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Xylyl bromide, also known as methylbenzyl bromide or T-stoff ('substance-T'), is any member or a mixture of
NIST record
* CAS RN : ''m''-xylyl bromide (3-methylbenzyl bromide, systematic name 1-(bromomethyl)-3-methylbenzene)
NIST record
* CAS RN : ''p''-xylyl bromide (4-methylbenzyl bromide, systematic name 1-(bromomethyl)-4-methylbenzene)
NIST record
In the absence of clarification, the name "xylyl bromide" may refer to any one of these isomers or a mixture of all three.
Hazardous Substances Data Bank (HSDB) record
{{Chemical agents Organobromides Lachrymatory agents World War I chemical weapons
Xylyl bromide, also known as methylbenzyl bromide or T-stoff ('substance-T'), is any member or a mixture of organic chemical compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The s ...
s with the molecular formula C6 H4(CH3)(CH2 Br). The mixture was formerly used as a tear gas and has an odor reminiscent of lilac. All members and the mixture are colourless liquids, although commercial or older samples appear yellowish.
Use as a weapon
Xylyl bromide is an irritant and lachrymatory agent. It has been incorporated inchemical weapon
A chemical weapon (CW) is a specialized munition that uses chemicals formulated to inflict death or harm on humans. According to the Organisation for the Prohibition of Chemical Weapons (OPCW), this can be any chemical compound intended as a ...
s since the early months of World War I. Some commentators say the first use was in August 1914, when the French attacked German soldiers with tear gas grenades, but the agent used in that incident was more likely to be ethyl bromoacetate
Ethyl bromoacetate is the chemical compound with the formula CH2BrCO2C2H5. It is the ethyl ester of bromoacetic acid and is prepared in two steps from acetic acid. It is a lachrymator and has a fruity, pungent odor. It is also a highly toxic alk ...
, which the French had tested before the war.
The first extensive use of xylyl bromide was the firing by German forces of 18,000 "T-shells" at Russian positions in the Battle of Bolimów
A battle is an occurrence of combat in warfare between opposing military units of any number or size. A war usually consists of multiple battles. In general, a battle is a military engagement that is well defined in duration, area, and force ...
in January 1915. The shells were modified 15 cm (6 inch) artillery shell
A shell, in a military context, is a projectile whose payload contains an explosive, incendiary, or other chemical filling. Originally it was called a bombshell, but "shell" has come to be unambiguous in a military context. Modern usage so ...
s containing an explosive charge and c. 3 kg (7 lb) xylyl bromide. The attack was a complete failure because the winter weather was too cold to permit an effective aerosol, and the agent was either blown back towards the German lines, fell harmlessly to the ground, or was insufficiently concentrated to cause damage. A similar attack at Nieuwpoort in March 1915 was also unsuccessful. Nevertheless, because of its ease of manufacture xylyl bromide was widely used in World War I, in particular as a component of the Germans' '' Weisskreuz'' (white cross) mixture.
Structural isomers
Three isomers, collectively referred to byCAS registry number
A CAS Registry Number (also referred to as CAS RN or informally CAS Number) is a unique identification number assigned by the Chemical Abstracts Service (CAS), US to every chemical substance described in the open scientific literature. It inclu ...
, are:
* CAS RN : ''o''-xylyl bromide (2-methylbenzyl bromide, systematic name 1-(bromomethyl)-2-methylbenzene)NIST record
* CAS RN : ''m''-xylyl bromide (3-methylbenzyl bromide, systematic name 1-(bromomethyl)-3-methylbenzene)
NIST record
* CAS RN : ''p''-xylyl bromide (4-methylbenzyl bromide, systematic name 1-(bromomethyl)-4-methylbenzene)
NIST record
In the absence of clarification, the name "xylyl bromide" may refer to any one of these isomers or a mixture of all three.
See also
*Chemical weapons in World War I
The use of toxic chemicals as weapons dates back thousands of years, but the first large scale use of chemical weapons was during World War I. They were primarily used to demoralize, injure, and kill entrenched defenders, against whom the indis ...
* Tetrabromo-o-xylene
α,α,α',α'-Tetrabromo-o-xylene is an organobromine compound with the formula C6H4(CHBr2)2. Three isomers of α,α,α',α'-Tetrabromoxylene exist, but the ortho derivative is most widely studied. It is an off-white solid. The compound is prep ...
References
External links
Hazardous Substances Data Bank (HSDB) record
{{Chemical agents Organobromides Lachrymatory agents World War I chemical weapons