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苯并咪唑

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苯并咪唑
IUPAC名
1H-benzimidazole
别名 1,3-苯并二氮唑
识别
CAS号 51-17-2  ☒N
51-17-2  ✓
PubChem 5798
ChemSpider 5593
SMILES
InChI
InChIKey HYZJCKYKOHLVJF-UHFFFAOYAX
ChEBI 41275
KEGG C02009
性质
化学式 C7H6N2
摩尔质量 118.136 g·mol⁻¹
外观 白色斜方及单斜结晶
熔点 170-172 ℃
沸点 > 360 ℃
危险性
警示术语 R:R20, R21, R22, R36, R37, R38
安全术语 S:S26, S36
MSDS External MSDS
欧盟分类 有害 (Xn)
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

苯并咪唑是一个多环芳香杂环化合物,由咪唑并合而成,分子式为C7H6N2维生素B12分子中,5,6-二甲基苯并咪唑为碱基中心相连。[1]

苯并咪唑与咪唑类似,也是制备氮杂环卡宾的常用原料。此类卡宾由N,N'-二取代的苯并咪唑用碱在2-位去质子化制得,用于制取过渡金属卡宾配合物[2][3]

制备

苯并咪唑由邻苯二胺甲酸[4] 或等量原甲酸三甲酯缩合制得:

C6H4(NH2)2 + HC(OCH3)3 → C6H4N(NH)CH + 3 CH3OH

2-取代的苯并咪唑可由此法用其他羧酸制备。[4]

参见

参考资料

  1. ^ H. A. Barker, R. D. Smyth, H. Weissbach, J. I. Toohey, J. N. Ladd, and B. E. Volcani. Isolation and Properties of Crystalline Cobamide Coenzymes Containing Benzimidazole or 5,6-Dimethylbenzimidazole. Journal of Biological Chemistry. 1960, 235 (2): 480–488 [2008-07-02]. (原始内容存档于2009-02-11). 
  2. ^ R. Jackstell, A. Frisch, M. Beller, D. Rottger, M. Malaun and B. Bildstein. Efficient telomerization of 1,3-butadiene with alcohols in the presence of in situ generated palladium(0)carbene complexes. Journal of Molecular Catalysis A: Chemical. 2002, 185 (1-2): 105–112. doi:10.1016/S1381-1169(02)00068-7. 
  3. ^ H. V. Huynh, J. H. H. Ho, T. C. Neo and L. L. Koh. Solvent-controlled selective synthesis of a trans-configured benzimidazoline-2-ylidene palladium(II) complex and investigations of its Heck-type catalytic activity. Journal of Organometallic Chemistry. 2005, 690 (16): 3854–3860. doi:10.1016/j.jorganchem.2005.04.053. 
  4. ^ 4.0 4.1 E. C. Wagner and W. H. Millett (1943). "Benzimidazole". Org. Synth.; Coll. Vol. 2: 65. 

延伸阅读

  • Grimmett, M. R. Imidazole and benzimidazole synthesis. Boston: Academic Press. 1997. ISBN 0-12-303190-7. 
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苯并咪唑
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