α-溴氰化苄

α-溴氰化苄或α-溴苯乙腈（BBC）是一种在第一次世界大战中由盟军引入的催泪剂，^[2]由于其极强的效果，它彻底改变了催泪剂的使用。它的毒性类似氯气。^[3]

Α-溴氰化苄
IUPAC名 (RS)-2-bromo-2-phenylacetonitrile
别名	α-bromobenzyl cyanide
识别
CAS号	5798-79-8  Y
PubChem	22044
ChemSpider	20715
SMILES	C1=CC=C(C=C1)C(C#N)Br
InChI	1/C8H6BrN/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8H
InChIKey	XUHFBOUSHUEAQZ-UHFFFAOYAJ
性质
化学式	C8H6BrN
摩尔质量	196.04 g·mol⁻¹
密度	1.539 g·cm−3（29 °C）[1]
熔点	29 °C（302 K）[1]
沸点	242 °C（515 K）[1]
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

合成与反应

α-溴氰化苄可由苯乙腈和溴^[4]或N-溴代丁二酰亚胺^[5]反应得到。

它和硫脲在乙醇中反应，可以得到5-苯基噻唑-2,4-二胺。^[6]它和二丁基碲在乙醚中反应，可以得到二丁基(氰基苯基甲基)溴化碲。^[7]

参考文献

1. "Hazardous Substances Data Bank" data were obtained from the National Library of Medicine (US). Retrieved from SciFinder. [2021-12-12].
2. Davies, W; MacLaren, J. A. 330. The reaction of α-bromobenzyl cyanide with ethyl xanthamidate (thioncarbamate). J. Chem. Soc. 1951: 1434–1437. doi:10.1039/JR9510001434.
3. AMOS A. FRIES and CLARENCE J. WEST. CHEMICAL WARFARE - First Edition. p 142-143
4. Lin Lei, Miho Tanishima, Atsushi Goto, Hironori Kaji, Yu Yamaguchi, Hiroto Komatsu, Takuya Jitsukawa, Michihiko Miyamoto. Systematic Study on Alkyl Iodide Initiators in Living Radical Polymerization with Organic Catalysts. Macromolecules. 2014-10-14, 47 (19): 6610–6618 [2021-12-12]. ISSN 0024-9297. doi:10.1021/ma501569j. （原始内容存档于2021-12-12） （英语）.
5. Wolfgang Eberbach, Joachim Roser. Thermally initiated reactions of (z)-epoxyhexenynes a facile preparation of 3,4-annulated furans. Tetrahedron. 1986-01, 42 (8): 2221–2234 [2021-12-12]. doi:10.1016/S0040-4020(01)90602-7 （英语）.
6. W. Davies, J. A. Maclaren, L. R. Wilkinson. 687. The synthesis and properties of 2 : 4-diaminothiazoles. Journal of the Chemical Society (Resumed). 1950: 3491 [2021-12-12]. ISSN 0368-1769. doi:10.1039/jr9500003491 （英语）.
7. Zhong, Qi; Cheng, Yulong; Shao, Jianguo; Liu, Changqing. Studies on the reaction of organotelluronium salts. Chinese Chemical Letters, 1991. 2 (1): 51-54.

外部链接

• Chapter VII Riot Control Agents. FM 8-9 NATO Handbook On the Medical Aspects of NBC Operation AMedP-6(B). FAS.org. [2021-12-12]. （原始内容存档于2021-04-17）.
• Major Chemical Weapons Introductions in World War I. CBWInfo.com. （原始内容存档于2010-09-19）.