苯并噻唑
苯并噻唑(英语:Benzothiazole)是一种芳香杂环化合物,化学式为C
7H
5NS,其性状为无色稍粘稠液体。苯并噻唑的多种衍生物常见于自然界或商品中。萤火虫萤光素也可以当做是苯并噻唑的一种衍生物。
苯并噻唑 | |||
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IUPAC名 1,3-Benzothiazole | |||
识别 | |||
CAS号 | 95-16-9 | ||
PubChem | 7222 | ||
ChemSpider | 6952 | ||
SMILES |
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InChI |
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InChIKey | IOJUPLGTWVMSFF-UHFFFAOYAC | ||
ChEBI | 45993 | ||
性质 | |||
化学式 | C7H5NS | ||
摩尔质量 | 135.19 g·mol−1 | ||
密度 | 1.238 g/mL | ||
熔点 | 2 °C(275 K) | ||
沸点 | 227-228 °C(500-501 K) | ||
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。 |
制备
苯并噻唑可由2-氨基苯硫酚和二甲基甲酰胺为原料反应得到。[1][2]
苯并噻唑的衍生物可以通过2-氨基苯硫酚和酰氯反应而得:[3]
- C6H4(NH2)SH + RC(O)Cl → C6H4(NH)SCR + HCl + H2O
用途
苯并噻唑天然存在于一些食物当中,也可以作为一种食品添加剂。[4]其气味似硫,味道似肉。[5]欧洲食品安全局评估苯并噻唑“以调味剂的水平摄入,没有安全风险”。[6]
参见
参考资料
- ^ Supill Chun, Sabyuk Yang, Young Keun Chung. Synthesis of benzothiazoles from 2-aminobenzenethiols in the presence of a reusable polythiazolium precatalyst under atmospheric pressure of carbon dioxide. Tetrahedron. 2017-06, 73 (25): 3438–3442 [2021-04-22]. doi:10.1016/j.tet.2017.05.003 (英语).
- ^ Hamid Mostafavi, Mohammad Reza Islami, Ehsan Ghonchepour, Ahmad Momeni Tikdari. Synthesis of 1H-1,3-benzimidazoles, benzothiazoles and 3H-imidazo[4,5-c]pyridine using DMF in the presence of HMDS as a reagent under the transition-metal-free condition. Chemical Papers. 2018-12, 72 (12): 2973–2978 [2021-04-22]. ISSN 2585-7290. doi:10.1007/s11696-018-0540-5 (英语).
- ^ T. E. Gilchrist "Heterocyclic Chemistry" 3rd Edition, Longman, 1992.
- ^ Lucille Le Bozec, Christopher J. Moody "Naturally Occurring Nitrogen–Sulfur Compounds. The Benzothiazole Alkaloids" Australian Journal of Chemistry 62(7) 639–647.doi:10.1071/CH09126
- ^ Benzothiazole. The Good Scents Company. [2020-10-06]. (原始内容存档于2020-10-23).
- ^ Flavouring Group Evaluation 76, (FGE.76) - Consideration of sulphur-containing heterocyclic compounds evaluated by JECFA (59th meeting) structurally related to thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29, miscellaneous. EFSA Journal. 2008, 6 (11): 875. doi:10.2903/j.efsa.2008.875.