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{{chembox |
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{{chembox |
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| verifiedrevid = 399695775 |
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| verifiedrevid = 399981012 |
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| ImageFile = 2-bromo-2-phenylacetonitrile-2D-skeletal.png |
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| ImageFile = 2-bromo-2-phenylacetonitrile-2D-skeletal.png |
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| ImageSize = 100 |
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| ImageSize = 100 |
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| IUPACName = (''RS'')-2-bromo-2-phenylacetonitrile |
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| IUPACName = (''RS'')-2-bromo-2-phenylacetonitrile |
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| OtherNames = α-bromobenzyl cyanide |
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| OtherNames = α-bromobenzyl cyanide |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| PubChem = 22044 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 27535 |
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| ChemSpiderID = 20715 |
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| SMILES = C1=CC=C(C=C1)C(C#N)Br |
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| InChI = 1/C8H6BrN/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8H |
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| InChI = 1/C8H6BrN/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8H |
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| InChIKey = XUHFBOUSHUEAQZ-UHFFFAOYAJ |
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| InChIKey = XUHFBOUSHUEAQZ-UHFFFAOYAJ |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| InChI1 = 1/C8H6BrN/c9-8-4-2-1-3-7(8)5-6-10/h1-4H,5H2 |
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| StdInChI = 1S/C8H6BrN/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8H |
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| InChIKey1 = BVCOJESIQPNOIF-UHFFFAOYAH |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| SMILES1 = Brc1ccccc1CC#N |
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| StdInChIKey = XUHFBOUSHUEAQZ-UHFFFAOYSA-N |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|??}} |
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| StdInChI = 1S/C8H6BrN/c9-8-4-2-1-3-7(8)5-6-10/h1-4H,5H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = BVCOJESIQPNOIF-UHFFFAOYSA-N |
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| CASNo = 5798-79-8 |
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| CASNo = 5798-79-8 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 29625 |
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| UNII = 7JP1R2F6C6 |
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| SMILES = N#CC(Br)c1ccccc1 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>8</sub>H<sub>6</sub>BrN |
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| Formula = C<sub>8</sub>H<sub>6</sub>BrN |
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| MolarMass = 196.04 g mol<sup>−1</sup> |
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| MolarMass = 196.04 g mol<sup>−1</sup> |
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| BoilingPt = |
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| Solubility = }} |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = }} |
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'''Bromobenzyl cyanide''' ('''BBC'''), also known in the military idiom as '''camite''' ('''CA'''), is an obsolete ]<ref>{{cite journal|title=330. The reaction of α-bromobenzyl cyanide with ethyl xanthamidate (thioncarbamate)|journal=J. Chem. Soc.|pages=1434–1437|doi=10.1039/JR9510001434|year=1951|last1=Davies|first1=W|last2=MacLaren|first2=J. A}}</ref> introduced in ] by the ], being a standard agent, along with ], adopted by the ].<ref>Chemical Warfare Bulletin. Vol 12. p 312</ref> When implemented in World War I, it revolutionized the use of tear agents due to their extreme potency. BBC is toxic like chlorine gas.<ref>AMOS A. FRIES and CLARENCE J. WEST. CHEMICAL WARFARE - First Edition. p 142-143</ref> |
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'''Bromobenzyl cyanide''' (BBC) is an obsolete ] introduced ] as a harassing gas by the ]. |
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==See also== |
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==See also== |
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==References== |
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==External links== |
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==External links== |
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* {{cite web | url = http://www.fas.org/nuke/guide/usa/doctrine/dod/fm8-9/3ch7.htm | publisher = FAS.org | work = FM 8-9 NATO Handbook On the Medical Aspects of NBC Operation AMedP-6(B)| title = Chapter VII Riot Control Agents }} |
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* {{cite web | url = http://www.cbwinfo.com/History/WWI.html | publisher = CBWInfo.com | title = Major Chemical Weapons Introductions in World War I | url-status = dead | archiveurl = https://web.archive.org/web/20100919085218/http://cbwinfo.com/History/WWI.html | archivedate = 2010-09-19 }} |
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