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苯甲腈

苯甲腈
苯甲腈的棒球模型
苯甲腈的填充模型
别名 氰基苯
识别
CAS号 100-47-0  checkY
PubChem 7505
ChemSpider 7224
SMILES
 
  • c1ccc(cc1)C#N
InChI
 
  • 1/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H
InChIKey JFDZBHWFFUWGJE-UHFFFAOYAY
KEGG C09814
性质
化学式 C7H5N
摩尔质量 103.04 g·mol⁻¹
密度 1.01 g/ml(20℃)[1]
熔点 −13 °C[1]
沸点 191 °C[1]
溶解性 10 g·l−1(20℃)[1]
折光度n
D
1.5289(20℃)[1]
危险性
警示术语 R:R21/22
安全术语 S:S2, S23
欧盟编号 608-012-00-3
欧盟分类 有害(Xn
NFPA 704
2
3
0
 
闪点 75 °C
自燃温度 550 °C
爆炸極限 1.4–7.2%
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

苯甲腈是具有示性式C6H5CN的芳香化合物,简写为PhCN。苯甲腈是一种無色,有甜杏仁味的液体。它可以通过苯甲酰胺脱水或者通过氰化钠溴苯反应制备。

應用

苯甲腈是一种有用的溶剂,可以做成許多衍生物。它和胺反应的生成物水解後可得到N-取代的苯甲酰胺。[2]它是通过与苯基溴化镁反应再甲醇解制备Ph2C=NH(沸点151 °C,8 mmHg)的前体。[3]

歷史

苯甲腈最早于1844年被德國化學家赫尔曼·斐林英语Hermann Fehling发现,他利用加热苯甲酸铵,使其分解的方式得到。[4]

2018年,苯甲腈被发现存在于星际物质中。[5]

危害

燃烧苯甲腈会产生含有氢氰酸的气体。[1]

参考文献

  1. ^ 1.0 1.1 1.2 1.3 1.4 1.5 Record of Benzonitril in the GESTIS Substance Database from the IFA英语Institute for Occupational Safety and Health
  2. ^ Cooper, F.C.; Partridge, M. W. (1963). "N-Phenylbenzamidine". Org. Synth.; Coll. Vol. 4: 769. 
  3. ^ Pickard, P. L.; Tolbert, T. L. (1973). "Diphenyl Ketimine". Org. Synth.; Coll. Vol. 5: 520. 
  4. ^ Hermann Fehling. Ueber die Zersetzung des benzoësauren Ammoniaks durch die Wärme. Annalen der Chemie und Pharmacie. 1844, 49 (1): 91–97. doi:10.1002/jlac.18440490106. 
  5. ^ McGuire, Brett A.; et al. Detection of the aromatic molecule benzonitrile (c\sC6H5CN) in the interstellar medium. Science. January 2018, 359 (6372): 202–205. Bibcode:2018Sci...359..202M. PMID 29326270. arXiv:1801.04228可免费查阅. doi:10.1126/science.aao4890. 

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苯甲腈
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