2-氨基-5-氯苯并噻唑 | 20358-00-3

• 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: 2-氨基-5-氯苯并噻唑
• 中文别名: 二盐酸邻联茴香胺；二盐酸邻联茴香胺盐酸盐；3,3'-二甲氧基联苯胺盐酸盐
• 英文名称: 2-amino-5-chlorobenzothiazole
• 英文别名: 5-chlorobenzo[d]thiazol-2-amine；5-chloro-2-aminobenzothiazole；5-chloro-1,3-benzothiazol-2-amine；2-Amino-5-chlor-benzthiazol
• CAS: 20358-00-3
• 化学式: C₇H₅ClN₂S
• mdl: MFCD00205355
• 分子量: 184.649
• InChiKey: AVVSRALHGMVQQW-UHFFFAOYSA-N

物化性质

• 熔点：
  199.0 to 203.0 °C
• 沸点：
  344.3±34.0 °C(Predicted)
• 密度：
  1.532±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H312,H315,H319,H335
• 储存条件：
  存放于惰性气体中，以避免与空气接触。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-5-chlorobenzo[d]thiazole
Synonyms: 5-Chlorobenzo[d]thiazol-2-amine

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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: 2-Amino-5-chlorobenzo[d]thiazole
CAS number: 20358-00-3

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H5ClN2S
Molecular weight: 184.6

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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 chloride, 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：

  2-氨基-5-氯苯并噻唑 在 sodium hydroxide 作用下， 以 水 、 乙二醇 为溶剂， 生成 2-氨基-4-氯苯硫醇
  参考文献：
  名称：

  Rh催化的不饱和中环NH内酰胺的不对称氢化：N-未保护的2,3-二氢-1,5-苯并噻唑酮的高度对映选择性合成。

  摘要：

  据报道，一种简单的制备1，5-苯并硫氮杂s的方法。在Rh / Zhaophos配合物的催化下，具有中等大小的环的不饱和环状NH内酰胺被平滑地氢化，具有很高的对映选择性。底物中的硫原子没有带来抑制作用，这是通过市售双膦配体观察到的。该方法已成功应用于（R）-（-）-噻嗪酮的放大合成。

  DOI：

  10.1021/acs.orglett.9b04478
• 作为产物：
  描述：

  4-氯-2-硝基苯基硫氰酸酯 在 盐酸 、 tin 作用下， 以 水 为溶剂， 以43%的产率得到2-氨基-5-氯苯并噻唑
  参考文献：
  名称：

  设计，合成和合成顺式-1,2-二氨基环己烷衍生物作为有效的Xa因子抑制剂。第一部分：探索5–6个稠合环作为S1的替代部分

  摘要：

  为了优化先前公开的因子Xa（fXa）抑制剂，合成了一系列顺式-1,2-二氨基环己烷衍生物。探索5-6个稠合环作为S1的替代部分，与临床候选化合物A相比，发现了两种化合物具有更高的溶解度和降低的食物效果。在这里，我们描述了一些预期化合物的合成和结构-活性关系（SAR），以及理化性质和药代动力学（PK）谱。

  DOI：

  10.1016/j.bmc.2009.10.023

文献信息

• Mimicking transition metals in borrowing hydrogen from alcohols
  作者：Ananya Banik、Jasimuddin Ahmed、Swagata Sil、Swadhin K. Mandal

  DOI：10.1039/d1sc01681d

  日期：——

  Borrowing hydrogen from alcohols, storing it on a catalyst and subsequent transfer of the hydrogen from the catalyst to an in situ generated imine is the hallmark of a transition metal mediated catalytic N-alkylation of amines. However, such a borrowing hydrogen mechanism with a transition metal free catalytic system which stores hydrogen molecules in the catalyst backbone is yet to be established

  从醇中借用氢气，将其储存在催化剂上，然后将氢气从催化剂转移到原位生成的亚胺，这是过渡金属介导的胺催化N-烷基化的标志。然而，这种在催化剂主链中储存氢分子的无过渡金属催化系统的借氢机制尚未建立。在此，我们证明苯酚基配体可以模仿过渡金属在储存和转移氢分子中的作用，从而导致借氢介导的醇类苯胺烷基化，包括广泛的底物范围。通过各种光谱技术、氘标记实验和 DFT 研究表征几种中间体，对机制途径进行了仔细检查，得出的结论是，基于苯酚基的主链通过脱芳构化过程依次添加 H + 、 H˙ 和一个电子，随后将其用作还原剂。相当于催化方式中的C-N双键。
• Chagas Disease Drug Discovery: Multiparametric Lead Optimization against <i>Trypanosoma cruzi</i> in Acylaminobenzothiazole Series
  作者：Charlotte Fleau、Angel Padilla、Juan Miguel-Siles、Maria T. Quesada-Campos、Isabel Saiz-Nicolas、Ignacio Cotillo、Juan Cantizani Perez、Rick L. Tarleton、Maria Marco、Gilles Courtemanche

  DOI：10.1021/acs.jmedchem.9b01429

  日期：2019.11.27

  responsible for Chagas disease. We selected compound 1 for lead optimization, aiming to improve in parallel its anti-T. cruzi activity (IC50 = 0.63 μM) and its human metabolic stability (human clearance = 9.57 mL/min/g). A total of 39 analogues of 1 were synthesized and tested in vitro. We established a multiparametric structure–activity relationship, allowing optimization of antiparasite activity, physicochemical

  酰基氨基苯并噻唑命中被确定为克氏锥虫复制的潜在抑制剂，锥虫是负责恰加斯病的寄生虫。我们选择化合物1进行铅优化，旨在同时提高其抗克鲁氏锥虫活性（IC 50 = 0.63μM）和其人类代谢稳定性（人类清除率= 9.57 mL / min / g）。总共合成了39种1的类似物，并在体外进行了测试。我们建立了多参数结构与活性的关系，从而可以优化抗寄生虫活性，理化参数和ADME特性。我们将化合物50鉴定为具有改进的体外抗T. cruzi活性的高级铅（IC50 = 0.079μM）和增强的代谢稳定性（人类清除率= 0.41 mL / min / g）和口服途径。在耐受性评估后，有50种药物显示出有希望的体内功效。
• Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists
  作者：Chetna Kharbanda、Mohammad Sarwar Alam、Hinna Hamid、Kalim Javed、Sameena Bano、Yakub Ali、Abhijeet Dhulap、Perwez Alam、M. A. Qadar Pasha

  DOI：10.1111/cbdd.12760

  日期：2016.9

  Piperine is an alkaloid responsible for the pungency of black pepper. In this study, piperine isolated from Piper nigrum L. was hydrolyzed under basic condition to obtain piperic acid and was used as precursor to carry out the synthesis of twenty piperine derivatives containing benzothiazole moiety. All the benzothiazole derivatives were evaluated for their antidiabetic potential by OGT test followed by

  胡椒碱是负责黑胡椒辛辣的生物碱。在这项研究中，从分离胡椒碱胡椒L.碱性条件下进行水解，得到胡椒酸和用作前体进行含有苯并噻唑部分20个胡椒碱衍生物的合成。通过OGT试验评估所有苯并噻唑衍生物的抗糖尿病潜力，然后在STZ诱导的糖尿病模型中评估活性衍生物。观察到二十种新型胡椒碱类似物中有九种（5b，6a-h）与罗格列酮（标准品）相比，具有明显更高的抗糖尿病活性。此外，评估了这些活性衍生物作为PPAR-γ激动剂的作用，证明了其作用机理。还研究了服用活性衍生物后对体重，脂质过氧化和肝毒性的影响，以进一步确立这些衍生物作为治疗糖尿病副作用较小的先导分子。
• 말단 아민기에 아릴 또는 헤테로아릴기가 치환된 신규한 히드라존 유도체 및 이의 용도
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY 한국과학기술연구원(319980077518) BRN ▼209-82-03522

  公开号：KR20200076655A

  公开（公告）日：2020-06-29

  본 발명은 말단 아민기에 아릴 또는 헤테로아릴기가 치환된 신규한 히드라존 유도체(hydrazone derivatives) 및 이의 용도에 관한 것이다.

  这项发明涉及末端氨基被芳基或杂芳基取代的新的腙衍生物(hydrazone derivatives)及其用途。
• SOLVENT-FREE SYNTHESIS OF SPIRO[3<i>H</i>-INDOLE-3,2′-THIAZOLIDINES]
  作者：Anshu Dandia、Ruby Singh、Kapil Arya

  DOI：10.1080/00304940309355848

  日期：2003.8

  interest,14 we now describe a solvent-free one-pot synthesis of some new spiro derivatives (4a-m) incorporating three heterocyclic moieties on preparative scale in few minutes (5-8 min) in an open vessel under microwave irradiation using unmodified domestic microwave oven. This method is of general applicability. Further, indolylimines (2) also represent a novel class of anti-HIV agents which appear to act

  噻唑烷酮 14 和螺~[吲哚-噻唑烷]~-~ 因其广泛的生物和药理活性而引起了广泛关注。螺[吲哚-噻唑烷酮] 系统早先通过两步法以 40-60% 的产率合成，使用靛红 3-亚胺作为关键中间体，它们本身获得了 hm 取代的靛红和芳香胺。经典方法包括共沸去除水 9Jo 或在脱水剂存在下进行反应，并在高温下使用大量溶剂数小时。此外，产品通常必须通过结晶或柱色谱法进行纯化。无溶剂方法是令人感兴趣的，因为它们具有高效率和选择性，产品易于分离和纯化，温和的反应条件和环境可接受性。'*微波活化与干反应技术相结合的潜力是成熟的技术。'~为了延续我们早期的兴趣，14我们现在描述了一些新的无溶剂一锅合成螺衍生物 (4a-m) 在几分钟内（5-8 分钟）在开放容器中使用未改良的家用微波炉在微波辐射下以制备规模包含三个杂环部分。该方法具有普遍适用性。此外，吲哚亚胺 (2) 也代表了一类新的抗 HIV 药物，它们似乎通过

表征谱图