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 chemical bond, bonds. Due to carbon's ability to Catenation, catenate (form chains with other carbon atoms), millions of organic c ...

s with the

molecular formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

C₆ H₄(CH₃)(CH₂ Br). The mixture was formerly used as a

tear gas Tear gas, also known as a lachrymator agent or lachrymator (), sometimes colloquially known as "mace" after the early commercial aerosol, is a chemical weapon that stimulates the nerves of the lacrimal gland in the eye to produce tears. In ad ...

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 Tear gas, also known as a lachrymator agent or lachrymator (), sometimes colloquially known as "mace" after the early commercial aerosol, is a chemical weapon that stimulates the nerves of the lacrimal gland in the eye to produce tears. In ad ...

. It has been incorporated in

chemical 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 World War I (28 July 1914 11 November 1918), often abbreviated as WWI, was one of the deadliest global conflicts in history. Belligerents included much of Europe, the Russian Empire, the United States, and the Ottoman Empire, with fightin ...

. Some commentators say the first use was in August 1914, when the French attacked German soldiers with

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 alky ...

, 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 ...

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 (Weiẞkreuz) is a World War I chemical warfare agent consisting of one or more lachrymatory agents: bromoacetone (BA), bromobenzyl cyanide (Camite), bromomethyl ethyl ketone (homomartonite, Bn-stoff), chloroacetone (Tonite, A-stoff), ...

'' (white cross) mixture.

Structural isomers

Three

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...

s, collectively referred to by

CAS 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.

References

External links

Hazardous Substances Data Bank (HSDB) record
{{Chemical agents Organobromides Lachrymatory agents World War I chemical weapons

Use as a weapon

Structural isomers

See also

References

External links