6-溴苯并噻唑 | 53218-26-1

• 物质功能分类: 医药中间体
• 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-溴苯并噻唑
• 中文别名: 6-溴-1,3-苯并噻唑
• 英文名称: 6-bromo-1,3-benzothiazole
• 英文别名: 6-bromobenzo[d]thiazole；6-bromobenzothiazole
• CAS: 53218-26-1
• 化学式: C₇H₄BrNS
• 分子量: 214.085
• InChiKey: YJOUISWKEOXIMC-UHFFFAOYSA-N

物化性质

• 熔点：
  52-54℃
• 沸点：
  143 °C(Press: 12 Torr)
• 密度：
  1.748±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 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：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  S26,S37/39
• 海关编码：
  2934999090
• 危险品标志：
  Xn
• 危险类别码：
  R22,R36/37/38
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  存放于惰性气体中，避免与空气接触。

SDS

Name:	6-Bromo-1 3-benzothiazole 97% Material Safety Data Sheet
Synonym:
CAS:	53218-26-1

Section 1 - Chemical Product MSDS Name:6-Bromo-1 3-benzothiazole 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
53218-26-1	6-Bromo-1,3-benzothiazole	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 53218-26-1: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 52 - 54 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C7H4BrNS
Molecular Weight: 214.09

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Not available.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 53218-26-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
6-Bromo-1,3-benzothiazole - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 53218-26-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 53218-26-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 53218-26-1 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用

6-溴-1,3-苯并噻唑属于苯并噻唑类衍生物。苯并噻唑是一类非常重要的含氮稠杂环化合物，在抗菌、抗寄生虫和抗肿瘤等方面具有潜在作用，同时也广泛应用于发光材料的合成，是一种广泛应用的化合物中间体。

制备

在微波反应器中加入2 mL水、3-溴苯并硫代酰胺（1 mmol）和碳酸铯（0.2 mmol），于固定功率120 W下反应10分钟。乙酸乙酯萃取，减压浓缩后，通过硅胶柱分离得到淡黄色固体，产率为93%。

反应信息

• 作为反应物：
  描述：

  6-溴苯并噻唑 在 [RuCl(P(C₆H₅)3)2(O(C₆H₄)NCH(C₄H₃N))] 、 bromamine B 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 5.5h， 以94%的产率得到2-amino-5-bromobenzenesulfonic acid
  参考文献：
  名称：

  Development of an efficient ruthenium catalyzed synthetic process and mechanism for the facile conversion of benzothiazoles to orthanilic acids

  摘要：

  Ruthenium-Schiff base complex catalyzed efficient protocol has been developed for the synthesis of orthanilic acids from benzothiazoles in good to excellent yields using N-haloamines. Hexa-coordinated ruthenium complex with Schiff base and triphenylphosphine ligands has been prepared and its catalytic function was invented for the synthesis of orthanilic acids. The synthetic process utilizes our efficient method for the selective and preferential oxidation of thiazole ring of benzothiazoles using N-haloamines without effecting phenyl ring. The detailed catalytic, mechanistic and kinetic investigations have been made for the synthetic reactions. Solvent isotope studies have been made in H2O-D2O and the reactions were carried out at different temperatures. Under the identical set of conditions, the kinetics of catalyzed reactions has been compared with uncatalyzed reactions and found that the catalyzed reactions are 9-11 folds faster. The catalytic constants (K-c) have been calculated for each N-haloamine at different temperatures and the values of activation parameters with respect to the catalyst have been evaluated. Spectroscopic evidence for the formation of 1:1 complex between N-haloamine and ruthenium has been obtained. The observed results have been explained by a plausible mechanism and the related rate law has been deduced. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2010.06.006
• 作为产物：
  描述：

  5-Bromo-2-nitrothiophenol 在 palladium on activated charcoal 、 氢气 作用下， 生成 6-溴苯并噻唑
  参考文献：
  名称：

  苯并稠合五元杂环化合物作为具有抗癌活性的微管蛋白聚合抑制剂的设计、合成和生物学评价

  摘要：

  设计并合成了一系列苯并稠合五元杂环化合物作为靶向秋水仙碱结合位点的新型微管蛋白抑制剂。其中，化合物4d对四种癌细胞系显示出最高的抗增殖活性，在B16-F10细胞中的IC 50值为4.9 μM。化合物 4d 在体外有效抑制微管蛋白聚合（IC 50为 13.1 μM）。此外，4d 诱导细胞周期停滞在 G2/M 期。最后，4d 以剂量依赖性方式抑制癌细胞的迁移。总之，这些结果表明化合物 4d 代表了一类新的微管蛋白抑制剂，值得进一步研究。

  DOI：

  10.1111/cbdd.13832
• 作为试剂：
  描述：

  乙酸-2-甲基苯基酯 在 盐酸 、 6-溴苯并噻唑 作用下， 以 水 、 乙腈 为溶剂， 以56 %的产率得到阿司匹林
  参考文献：
  名称：

  一种无金属光催化氧化制备芳香酸的方法

  摘要：

  本发明公开了一种无金属光催化氧化制备芳香酸的方法，包括如下步骤：将如式(Ⅰ)所示的化合物、光催化剂、添加剂加入到溶剂中，曝露在空气中，在光源照射下于25‑60℃搅拌反应，待反应结束后，反应液经后处理得到如式(Ⅱ)所示的芳香酸化合物，其反应方程式如下：其中，Ar为苯环、呋喃基、噻吩基、萘基或二苯酮，Ar基团上的H被R1单取代，取代基R1为烷基、取代羟基、醛基或取代烷基，Ar基团上的H被R2取代或不取代，取代时R2为单取代或多取代，n＝1～2，n取整数，取代基R2为烷基、烷氧基、卤素、三氟甲基、芳基，取代芳基或取代酚羟基。本发明通过在光照条件下，以氮杂环作为光催化剂，降低了生产成本，其操作简单，反应条件温和。

  公开号：

  CN115433076B

文献信息

• Metal-, Photocatalyst-, and Light-Free Minisci C–H Alkylation of <i>N</i>-Heteroarenes with Oxalates
  作者：Jianyang Dong、Zhen Wang、Xiaochen Wang、Hongjian Song、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.joc.9b00972

  日期：2019.6.7

  for metal-, photocatalyst-, and light-free Minisci C–H alkylation reactions of N-heteroarenes with alkyl oxalates derived from primary, secondary, and tertiary alcohols. The protocol uses environmentally benign persulfate as a stoichiometric oxidant and does not require high temperatures or large excesses of either of the substrates, making the procedure suitable for late-stage C–H alkylation of complex

  在此，我们报告了N-杂芳烃与衍生自伯醇、仲醇和叔醇的草酸烷基酯的无金属、光催化剂和无光 Minisci C-H 烷基化反应的温和方案。该协议使用对环境无害的过硫酸盐作为化学计量氧化剂，不需要高温或任何一种底物的大量过量，使得该程序适用于复杂分子的后期 C-H 烷基化。值得注意的是，可以使用该协议对几种药物和天然产品进行功能化或制备，从而证明其实用性。
• [EN] CYCLIC SULFAMIDE COMPOUNDS AND METHODS OF USING SAME<br/>[FR] COMPOSÉS DE SULFAMIDE CYCLIQUE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ASSEMBLY BIOSCIENCES INC

  公开号：WO2018160878A1

  公开（公告）日：2018-09-07

  The present disclosure provides, in part, cyclic sulfamide compounds, and pharmaceutical compositions thereof, useful as modulators of Hepatitis B (HBV) core protein, and methods of treating Hepatitis B (HBV) infection.

  本公开提供了部分环磺胺化合物及其药物组合物，可用作乙型肝炎（HBV）核心蛋白的调节剂，并用于治疗乙型肝炎（HBV）感染的方法。
• Process for preparation of benzo[f]quinolinones
  申请人：Eli Lilly and Company

  公开号：US05578724A1

  公开（公告）日：1996-11-26

  A series of benzoquinolin-3-ones are pharmaceuticals effective in treating conditions consequent on both Type I and Type II 5.alpha.-reductase and their preparation is disclosed.

  一系列苯醌啉-3-酮类药物在治疗由I型和II型5α-还原酶引起的疾病方面具有有效性，并且其制备方法已被披露。
• Mild Palladium-Catalyzed Cyanation of (Hetero)aryl Halides and Triflates in Aqueous Media
  作者：Daniel T. Cohen、Stephen L. Buchwald

  DOI：10.1021/ol5032359

  日期：2015.1.16

  A mild, efficient, and low-temperature palladium-catalyzed cyanation of (hetero)aryl halides and triflates is reported. Previous palladium-catalyzed cyanations of (hetero)aryl halides have required higher temperatures to achieve good catalytic activity. This current reaction allows the cyanation of a general scope of (hetero)aryl halides and triflates at 2–5 mol % catalyst loadings with temperatures

  据报道，轻度，有效和低温钯催化的（杂）芳基卤化物和三氟甲磺酸酯的氰化反应。先前钯催化的（杂）芳基卤化物的氰化需要更高的温度以实现良好的催化活性。该当前反应可以使一般范围的（杂）芳基卤化物和三氟甲磺酸酯在催化剂负载量为2％至5％的条件下从rt到40°C进行氰化。这种温和的方法适用于逆转录酶抑制剂lersivirine的合成。
• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：MISSION THERAPEUTICS LTD

  公开号：WO2016046530A1

  公开（公告）日：2016-03-31

  The present invention relates to novel compounds and methods for the manufacture of inhibitors of deubiquitylating enzymes (DUBs). In particular, the invention relates to the inhibition of ubiquitin C-terminal hydrolase L1 (UCHL1). The invention further relates to the use of DUB inhibitors in the treatment of cancer and other indications. Compounds of the invention include compounds having the formula (I) or a pharmaceutically acceptable salt thereof, wherein R1 to R8 are as defined herein.

  本发明涉及新型化合物和制备去泛素化酶（DUBs）抑制剂的方法。具体而言，本发明涉及抑制泛素C端水解酶L1（UCHL1）。本发明进一步涉及在癌症和其他适应症治疗中使用DUB抑制剂。本发明的化合物包括具有式（I）或其药用可接受盐的化合物，其中R1至R8如本文所定义。

表征谱图