苯并噻唑

苯并噻唑(英語:Benzothiazole)是一种芳香杂环化合物,化学式为C
7
H
5
NS
,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
IUPAC名
1,3-Benzothiazole
识别
CAS号 95-16-9  ✓
PubChem 7222
ChemSpider 6952
SMILES
InChI
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(272 K)
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

制备编辑

苯并噻唑可由2-氨基苯硫酚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-氨基苯硫酚酰氯反应而得:[3]

C6H4(NH2)SH + RC(O)Cl → C6H4(NH)SCR + HCl + H2O

用途编辑

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]欧洲食品安全局英语European Food Safety Authority评估苯并噻唑“以调味剂的水平摄入,没有安全风险”。[6]

参见编辑

参考资料编辑

  1. ^ 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). 
  2. ^ 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). 
  3. ^ T. E. Gilchrist "Heterocyclic Chemistry" 3rd Edition, Longman, 1992.
  4. ^ 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
  5. ^ Benzothiazole. The Good Scents Company. [2020-10-06]. 
  6. ^ 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. 

外部链接编辑