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 formulaC6H4(CH3)(CH2Br). The mixture was formerly used as a tear gas and has an odor reminiscent of lilac.[1] All members and the mixture are colourless liquids, although commercial or older samples appear yellowish.
From left to right, the ortho-, meta-, and para-isomers of xylyl bromide
Xylyl bromide is an irritant and lachrymatory agent. It has been incorporated in chemical weapons 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,[2][3] but the agent used in that incident was more likely to be ethyl bromoacetate, which the French had tested before the war.[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 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 in March 1915 was also unsuccessful.[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.
^Ashutosh Jogalekar. "Chemists and bad smells (and sulfur): A productive pairing". Scientific American. Retrieved 2020-01-04.
^Chris Trueman. "Poison Gas and World war One". History Learning Site. Retrieved 2010-08-26.
^Michael Duffy (August 22, 2009). "Weapons of War - Poison Gas". firstworldwar.com. Retrieved 2010-08-26.
^ abCorey J Hilmas, Jeffery K Smart, Benjamin A Hill (2008). "Chapter 2: History of Chemical Warfare (pdf)". Medical Aspects of Chemical Warfare(PDF). Borden Institute. pp. 12–14.{{cite book}}: CS1 maint: uses authors parameter (link)
External links
Hazardous Substances Data Bank (HSDB) record
March 04, 2023
xylyl, bromide, also, known, methylbenzyl, bromide, stoff, substance, member, mixture, organic, chemical, compounds, with, molecular, formula, c6h4, ch2br, mixture, formerly, used, tear, odor, reminiscent, lilac, members, mixture, colourless, liquids, although. 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 The mixture was formerly used as a tear gas and has an odor reminiscent of lilac 1 All members and the mixture are colourless liquids although commercial or older samples appear yellowish From left to right the ortho meta and para isomers of xylyl bromide Contents 1 Use as a weapon 2 Structural isomers 3 See also 4 References 5 External linksUse as a weapon EditXylyl bromide is an irritant and lachrymatory agent It has been incorporated in chemical weapons 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 2 3 but the agent used in that incident was more likely to be ethyl bromoacetate which the French had tested before the war 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 Bolimow 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 in March 1915 was also unsuccessful 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 Structural isomers EditThree isomers collectively referred to by CAS registry number 35884 77 6 are CAS RN 89 92 9 o xylyl bromide 2 methylbenzyl bromide systematic name 1 bromomethyl 2 methylbenzene NIST record CAS RN 620 13 3 m xylyl bromide 3 methylbenzyl bromide systematic name 1 bromomethyl 3 methylbenzene NIST record CAS RN 104 81 4 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 EditChemical weapons in World War I Tetrabromo o xyleneReferences Edit Ashutosh Jogalekar Chemists and bad smells and sulfur A productive pairing Scientific American Retrieved 2020 01 04 Chris Trueman Poison Gas and World war One History Learning Site Retrieved 2010 08 26 Michael Duffy August 22 2009 Weapons of War Poison Gas firstworldwar com Retrieved 2010 08 26 a b Corey J Hilmas Jeffery K Smart Benjamin A Hill 2008 Chapter 2 History of Chemical Warfare pdf Medical Aspects of Chemical Warfare PDF Borden Institute pp 12 14 a href Template Cite book html title Template Cite book cite book a CS1 maint uses authors parameter link External links EditHazardous Substances Data Bank HSDB record Retrieved from https en wikipedia org w index php title Xylyl bromide amp oldid 1136159546, wikipedia, wiki, book, books, library,
