Xylyl bromide

Xylyl-bromide, also known as methylbenzyl bromide or T-stoff ('substance-T'), is any member or a mixture of organic chemical compounds with the molecular formula C6H4(CH3)(CH2Br).

[1] All members and the mixture are colourless liquids, although commercial or older samples appear yellowish.

[4] 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 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.

[4] 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.

From left to right, the ortho -, meta -, and para -isomers of xylyl bromide