6-溴-2-巯基苯并噻唑 | 51618-30-5

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 6-溴-2-巯基苯并噻唑
• 中文别名: 2-巯基-6-溴苯并噻唑
• 英文名称: 6-bromo-2-mercaptobenzothiazole
• 英文别名: 6-bromobenzo[d]thiazole-2-thiol；6-bromo-3H-1,3-benzothiazole-2-thione
• CAS: 51618-30-5
• 化学式: C₇H₄BrNS₂
• 分子量: 246.151
• InChiKey: KNFZKHAWHVYFFI-UHFFFAOYSA-N

物化性质

• 熔点：
  260-263 °C
• 沸点：
  359.7±44.0 °C(Predicted)
• 密度：
  1.93

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Bromobenzo[d]thiazole-2(3h)-thione
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 6-Bromobenzo[d]thiazole-2(3h)-thione
CAS number: 51618-30-5

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C7H4BrNS2
Molecular weight: 246.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen bromide, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  6-溴-2-巯基苯并噻唑 在 磺酰氯 、 水 作用下， 反应 3.25h， 以96%的产率得到2-氯-6-溴苯并噻唑
  参考文献：
  名称：

  2-巯基苯并噻唑的水促进氯化反应

  摘要：

  摘要 取代的苯并噻唑由于其药理特性，在药物化学中起着重要作用。它们的2-取代衍生物通常由2-氯苯并噻唑制备，而后者又可以使用硫酰氯由2-巯基前体合成。在实践中，这种看似直接和广泛使用的反应可能会因重现性差和反应产率低而受到阻碍。在此交流中，我们报告说，将水简单添加到反应中会显着提高反应效率。我们将此效应归因于通过磺酰氯的部分水解而形成酸。该假设得到以下观察结果的支持：在一些无水酸性添加剂的存在下，收率也得到了提高。 取代的苯并噻唑由于其药理特性，在药物化学中起着重要作用。它们的2-取代衍生物通常由2-氯苯并噻唑制备，而后者又可以使用硫酰氯由2-巯基前体合成。在实践中，这种看似直接和广泛使用的反应可能会因重现性差和反应产率低而受到阻碍。在此交流中，我们报告说，将水简单添加到反应中会显着提高反应效率。我们将此效应归因于通过磺酰氯的部分水解而形成酸。该假设得到以下观察结果的支持：在一些无水酸性添加剂的存在下，收率也得到了提高。

  DOI：

  10.1055/s-0036-1591553
• 作为产物：
  描述：

  2,4-二溴苯胺 在 二硫化碳 、 sodium methylate 作用下， 以 N-甲基乙酰胺 、 水 为溶剂， 生成 6-溴-2-巯基苯并噻唑
  参考文献：
  名称：

  Process for the preparation of 2-mercaptobenzothiazoles

  摘要：

  通过将相应的2-卤代苯胺与碱金属黄羟酸盐或碱土金属黄羟酸盐或在碱存在下与CS.sub.2反应，制备（可选择性取代的）2-巯基苯并噻唑。

  公开号：

  US04431813A1

文献信息

• Efficient Monofluoroalkylation of Thiophenols or Phenols with α-Bromo-α-Fluoroketones under Mild Conditions
  作者：Jingjing Wu、Fanhong Wu、Zhi Li、Mougui Fang、Yunli Liu、Yecheng Liu

  DOI：10.1055/a-1395-4788

  日期：2021.7

  nucleophilic substitution reaction between α-bromo-α-fluoroketones and thiophenols or phenols is reported for the synthesis of α-fluoro-β-ketosulfides or α-fluoro-β-ketone ethers in yields ranging from 78–93%. This method exhibits good functional group tolerance and a broad scope of nucleophilic substrates, including natural phenolic compounds.

  据报道，α-溴-α-氟代酮与硫酚或苯酚之间的有效亲核取代反应可合成α-氟代-β-酮硫醚或α-氟代-β-酮醚，产率为78-93％。该方法表现出良好的官能团耐受性和广泛的亲核底物，包括天然酚类化合物。
• Metal-free C–H mercaptalization of benzothiazoles and benzoxazoles using 1,3-propanedithiol as thiol source
  作者：Yan Xiao、Bing Jing、Xiaoxia Liu、Hongyu Xue、Yajun Liu

  DOI：10.3762/bjoc.15.24

  日期：——

  A facile and effective C–H functionalization strategy for the synthesis of 2-mercaptobenzothiazoles and 2-mercaptobenzoxazoles is described. 1,3-Propanedithiol was employed to convert benzothiazoles and benzoxazoles to the corresponding heteroarylthiols in the presence of potassium hydroxide and DMSO. This novel protocol is featured by direct C–H mercaptalization of heteroarenes and a simple reaction system.

  描述了一种简便有效的C-H官能化策略，用于合成2-巯基苯并噻唑和2-巯基苯并噁唑。在氢氧化钾和二甲基亚砜存在下，采用1,3-丙二硫醇将苯并噻唑和苯并噁唑转化为相应的杂环硫醇。这种新颖的方案以对杂环烃的直接C-H巯基化和简单的反应体系为特点。
• Substitution‐Modulated Anticancer Activity of Half‐Sandwich Ruthenium(II) Complexes with Heterocyclic Ancillary Ligands
  作者：Raja Mitra、Ashoka G. Samuelson

  DOI：10.1002/ejic.201402205

  日期：2014.8

  half-sandwich ruthenium complexes with heterocyclic ligands have been synthesized (H1-H10). The substituents on the ancillary heterocyclic ligands were varied to understand the effect of substitution on anticancer activity. The crystallographic characterization of five complexes confirms that they adopt three-legged piano-stool structures and are stabilized by intramolecular hydrogen bonding. Complexes H2 and

  已经合成了十种具有杂环配体的新型有机金属半夹心钌配合物（H1-H10）。改变辅助杂环配体上的取代基以了解取代对抗癌活性的影响。五种配合物的晶体学表征证实它们采用三足钢琴凳结构，并通过分子内氢键稳定。配合物 H2 和 H3 在固态下也表现出卤素键合。在水性介质中，配合物形成双核钌物质。具有无细胞毒性杂环、6-氟-2-巯基苯并噻唑的复合物 H1 和具有未取代的 2-巯基苯并噻唑的复合物 H11 对 A2780 和 KB 细胞系的活性最强。辅助配体上的 H 原子被 Cl 或 Br 原子取代导致抗癌活性降低。除氟取代的 H5 外，与巯基苯并恶唑 (H6-H9) 的复合物对所有测试细胞系均无活性。钌与巯基萘咪唑 (H10) 和巯基苯并咪唑 (H13) 的配合物不显示任何抗癌活性。当与小牛胸腺 (CT) DNA 一起孵育时，活性复合物显示出双相熔解曲线。这些复合物仅在较小程度上抑制硫氧还蛋白还原酶 (TrxR)
• 对氨基水杨酸唑类衍生物及其制备方法和应用
  申请人：西南大学

  公开号：CN112028833B

  公开（公告）日：2022-07-05

  本发明公开了对氨基水杨酸唑类衍生物及其制备方法和应用，属于药物合成技术领域。对氨基水杨酸唑类衍生物的结构式如下。抗菌活性测定结果表明，本发明的对氨基水杨酸唑类衍生物对常见致病菌抑制活性整体很好，部分分子对毕赤酵母菌的抑菌活性强于或相当于阳性药物氟康唑，所有分子对柑橘胶孢炭疽病菌的抑制活性较好、部分分子与阳性对照咪鲜胺的抑制活性相当或更强，多数分子对柑橘溃疡病菌具有良好的抑制作用。抗肿瘤细胞活性测定结果显示，本发明的对氨基水杨酸唑类衍生物对三种肿瘤细胞均有抑制作用。本发明的对氨基水杨酸唑类衍生物在抗细菌、抗真菌、抗柑橘病菌和抗肿瘤领域具有潜在的应用前景。
• Copper-Catalyzed Coupling Reactions of Cyclobutanone Oxime Esters with Sulfur Nucleophiles at Room Temperature
  作者：Mingchuang He、Zhaohua Yan、Fuyuan Zhu、Sen Lin

  DOI：10.1021/acs.joc.8b02707

  日期：2018.12.21

  A copper-catalyzed iminyl radical-mediated C–C bond cleavage/cross-coupling tandem reaction of cyclobutanone oxime esters with aryl thiols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) at room temperature was developed, and aryl cyanopropyl sulfides were smoothly synthesized in 20–88% yields. By altering the copper reagent and the molar ratio of cyclobutanone oxime ester/aryl thiol/DBU

  在室温下1,8-二氮杂双环[5.4.0]十一烷基-7-烯（DBU）存在下，环丁酮肟酯与芳基硫醇的铜催化亚氨基自由基介导的CC键断裂/交叉偶联串联反应随着温度的升高，芳基氰基丙基硫醚以20–88％的收率顺利合成。通过改变铜试剂和环丁酮肟酯/芳基硫醇/ DBU的摩尔比，选择性生成N-芳硫基环丁酮亚胺的替代产物，收率为50-91％。使用该方案，在非常温和的条件下无需使用光催化和电催化技术即可实现使用芳基硫醇作为硫源的C–S键和N–S键的形成。