| 苯并咪唑 | |
|---|---|
| |
| |
| IUPAC名 1H-benzimidazole | |
| 别名 | 1,3-苯并二氮唑 |
| 识别 | |
| CAS号 | 51-17-2  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，由苯和咪唑并合而成，分子式为C7H6N2。维生素B12分子中，5,6-二甲基苯并咪唑为碱基与钴中心相连。[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
- 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
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 4.0 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.