Xylyl bromide
Xylyl bromide, also known as methylbenzyl bromide or T-stoff, is a poisonous organic chemical compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...

Bromine ") is a chemical element with the symbol Br, an atomic number of 35, and an atomic mass of 79.904. It is in the halogen element group. The element was isolated independently by two chemists, Carl Jacob Löwig and Antoine Jerome Balard, in 1825–1826...

, formerly used as a tear gas. Physically it is a colourless liquid (melting point 21°C) with a pleasant aromatic odour.

Use as a weapon

Xylyl bromide is highly toxic, irritant and lachrymatory
Lachrymatory agent
Tear gas, formally known as a lachrymatory agent or lachrymator , is a non-lethal chemical weapon that stimulates the corneal nerves in the eyes to cause tears, pain, and even blindness...

, and has been incorporated in chemical weapons since the early months of World War I
World War I
World War I , which was predominantly called the World War or the Great War from its occurrence until 1939, and the First World War or World War I thereafter, was a major war centred in Europe that began on 28 July 1914 and lasted until 11 November 1918...

. 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
Ethyl 2-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.-Applications:...

, 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 in January 1915. The shells were modified 15 cm (6 inch) artillery shells 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
Nieuwpoort, Belgium
Nieuwpoort is a municipality located in Flanders, one of the three regions of Belgium, and in the Flemish province of West Flanders. The municipality comprises the city of Nieuwpoort proper and the towns of Ramskapelle and Sint-Joris. On January 1, 2008 Nieuwpoort had a total population of 11,062....

 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 (chemical warfare)
White Cross is a World War I chemical warfare agent consisting of one or more lachrymatory agents: bromoacetone , bromobenzyl cyanide , bromomethyl ethyl ketone , chloroacetone , ethyl bromoacetate, and/or xylyl bromide.During World war I, White Cross was also a generic code name used by the...

(white cross) mixture.

Structural isomers

The three isomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...

s, collectively referred to by CAS registry number
CAS registry number
CAS Registry Numbersare unique numerical identifiers assigned by the "Chemical Abstracts Service" toevery chemical described in the...

, are:
  • CAS RN: o-xylyl bromide (2-methylbenzyl bromide, systematic name 1-(Bromomethyl)-2-methyl-benzene) (NIST record)
  • CAS RN: m-xylyl bromide (3-methylbenzyl bromide, systematic name 1-(Bromomethyl)-3-methyl-benzene) (NIST record)
  • CAS RN: p-xylyl bromide (4-methylbenzyl bromide, systematic name 1-(Bromomethyl)-4-methyl-benzene) (NIST record)

External links

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