2-(4-氨基苯基)-6-甲基苯并噻唑 | 92-36-4

• 物质功能分类: 有机原料 - 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: 2-(4-氨基苯基)-6-甲基苯并噻唑
• 中文别名: 4-(6-甲基-2-苯并噻唑)苯胺；2-对氨基苯基-6-甲基苯噻唑；脱氢硫代对甲苯胺；2-对氨基苯基-6-甲基苯并噻唑
• 英文名称: 2-(4-Aminophenyl)-6-methylbenzothiazole
• 英文别名: 2-(4-aminophenyl)-6-methyl-1,3-benzothiazole；4-(6-methylbenzo[d]thiazol-2-yl)aniline；4-(6-methyl-1,3-benzothiazol-2-yl)aniline
• CAS: 92-36-4
• 化学式: C₁₄H₁₂N₂S
• mdl: MFCD00005780
• 分子量: 240.329
• InChiKey: XRTJYEIMLZALBD-UHFFFAOYSA-N

物化性质

• 熔点：
  191-196°C
• 沸点：
  434°C
• 密度：
  1.1769 (rough estimate)
• 溶解度：
  ≥ 24mg/mL，溶于 DMSO
• LogP：
  3.56 at 25℃
• 物理描述：
  2-(4-aminophenyl)-6-methylbenzothiazole appears as light tan or light orange powder. Solutions have a violet-blue fluorescence. (NTP, 1992)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温和干燥环境中使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(6-Methyl-2-benzothiazolyl)benzeneamine
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: 4-(6-Methyl-2-benzothiazolyl)benzeneamine
CAS number: 92-36-4

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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.
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: C14H12N2S
Molecular weight: 240.3

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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, 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

制备方法与用途

简介

2-(4-氨基苯基)-6-甲基苯并噻唑是一种杂环有机物，可用作燃料的中间体。该化合物还可进一步加工成脱氢硫代对甲苯胺单磺酸、双磺酸及其他染料中间体。

此外，它也是合成纸用染料的重要中间体。

反应信息

• 作为反应物：
  描述：

  2-(4-氨基苯基)-6-甲基苯并噻唑 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 N-[2-[2-[2-[2-[3-(ethylamino)-3-oxopropoxy]ethoxy]ethoxy]ethoxy]ethyl]-3-[4-(6-methyl-1,3-benzothiazol-2-yl)anilino]propanamide
  参考文献：
  名称：

  寡价淀粉样蛋白结合剂可减少 SEVI 介导的 HIV-1 感染增强

  摘要：

  本文评估了寡价淀粉样蛋白结合分子作为潜在药物的用途，该药物可以减少精液源性病毒感染增强子（SEVI）原纤维对细胞中人类免疫缺陷病毒-1（HIV-1）感染的增强。精液中发现的这些天然存在的淀粉样原纤维被认为是可以促进 HIV-1 病毒颗粒与免疫细胞附着和内化的介质。因此，能够降低 SEVI 在 HIV-1 感染中的作用的分子可能代表了一种降低人类 HIV-1 性传播率的新策略。在这里，我们评估了一组合成的苯并噻唑苯胺（BTA，一种已知的淀粉样蛋白结合分子）寡价衍生物，了解它们与聚集的淀粉样肽协同结合并中和 SEVI 在 HIV-1 感染中的作用的能力。我们证明，这些 BTA 衍生物表现出与聚集淀粉样蛋白的结合随着寡聚物价数增加而增加的总体趋势。重要的是，我们发现与 BTA 单体相比，BTA 寡聚物在减少细胞中 SEVI 介导的 HIV-1 感染方面表现出更好的能力，与之前报道的单体 BTA 衍生物相比，五聚物的功效提高了

  DOI：

  10.1021/ja210931b
• 作为产物：
  描述：

  6-甲基-2-(4-硝基苯基)苯并噻唑 在 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以95%的产率得到2-(4-氨基苯基)-6-甲基苯并噻唑
  参考文献：
  名称：

  2-（4-氨基苯基）苯并噻唑衍生物作为光敏剂的合成及生物学评价

  摘要：

  使用外源光敏剂的光动力疗法（PDT）目前已被批准用于治疗基底细胞癌（BCC）。2-（4-氨基苯基）苯并噻唑（6）由发色结构组成，可吸收UVA（315-400 nm）中的光。这些结果鼓励我们设计和合成各种2-苯基苯并噻唑（6）。在本文中研究了UVC激活的6在BCC细胞中诱导的光敏效应所涉及的凋亡机制。用6 -UVA处理的细胞显示出一些凋亡特征，包括亚G1群体的增加，膜联蛋白V结合的显着增加以及caspase-3的激活。6-UVA诱导线粒体膜电位（Δ降低ψ公吨），并通过增强的ROS产生和胞外信号调节激酶（ERK）和p38 MAPK表达的促进磷酸ATP。这些结果表明6- UVA在涉及ERK和p38活化的线粒体过程中引起光敏作用，并最终导致BCC细胞凋亡。

  DOI：

  10.1016/j.bmc.2010.04.082

文献信息

• 1-Phenyl-<i>N</i>-(benzothiazol-2-yl)methanimine derivatives as Middle East respiratory syndrome coronavirus inhibitors
  作者：Min-Qi Hu、Heng Li、Ying Lin、Ying Zhang、Jie Tang、Jian-Ping Zuo、Li-Fang Yu、Xian-Kun Tong、Wei Tang、Fan Yang

  DOI：10.1039/d0ra08442e

  日期：——

  A series of novel 1-phenyl-N-(benzothiazol-2-yl)methanimine derivatives were synthesized and their in vitro inhibitory potencies were evaluated on MERS-S pseudovirus.

  一系列新颖的1-苯基-N-(苯并噻唑-2-基)甲醛亚胺衍生物被合成，并在MERS-S假病毒上评估了它们的体外抑制效力。
• Discovery and Characterization of Benzimidazole Derivative XY123 as a Potent, Selective, and Orally Available RORγ Inverse Agonist
  作者：Xishan Wu、Hui Shen、Yan Zhang、Chao Wang、Qiu Li、Cheng Zhang、Xiaoxi Zhuang、Chenchang Li、Yudan Shi、Yanli Xing、Qiuping Xiang、Jinxin Xu、Donghai Wu、Jinsong Liu、Yong Xu

  DOI：10.1021/acs.jmedchem.1c00763

  日期：2021.6.24

  (IC50) value of 64 nM and showed excellent selectivity against other nuclear receptors. 27h also potently suppressed cell proliferation, colony formation, and the expression of androgen receptor (AR)-regulated genes in AR-positive prostate cancer cell lines. In addition, 27h demonstrated good metabolic stability and a pharmacokinetic property with reasonable oral bioavailability (32.41%) and moderate half-life

  受体相关孤儿受体γ（RORγ）已成为治疗癌症和炎症性疾病的一个有吸引力的治疗靶点。在此，我们报告了我们在苯并噻唑和苯并咪唑衍生物作为 RORγ 新型反向激动剂的发现、优化和评估方面所做的努力。代表性化合物27h （命名为XY123）有效抑制RORγ转录活性，半数抑制浓度（IC 50 ）值为64 nM，并对其他核受体表现出优异的选择性。 27h还有效抑制 AR 阳性前列腺癌细胞系中的细胞增殖、集落形成和雄激素受体 (AR) 调节基因的表达。此外， 27h表现出良好的代谢稳定性和药代动力学特性，具有合理的口服生物利用度 (32.41%) 和中等的半衰期 ( t 1/2 = 4.98 h)。值得注意的是，口服化合物27h在小鼠22Rv1异种移植肿瘤模型中实现了完全且持久的肿瘤消退。化合物27h可能作为一种新的有价值的先导化合物，用于进一步开发治疗前列腺癌的药物。
• Synthesis of 4-oxopyrimidinium and 4-oxo-1,4-dihydropyrimidines
  作者：Irina V. Vedernikova、Achiel Haemers、Yuryi I. Ryabukhin

  DOI：10.1002/jhet.5570360115

  日期：1999.1

  The synthesis of N1-substituted 4-pyrimidones is described. These compounds were prepared from their corresponding 4-oxopyrimidinium perchlorates or from a reaction of a primary amine with a N-acyl-β-ketoamide.

  描述了N 1-取代的4-嘧啶酮的合成。这些化合物由其相应的4-氧代嘧啶高氯酸盐或伯胺与N-酰基-β-酮酰胺的反应制备。
• Synthesis of 2-(4-aminophenyl)benzothiazoles using MF resin supported H+ under solvent free conditions
  作者：Yingjie Lei、Xinshi Wu、Guochun Zhang、Cuiling Ai

  DOI：10.1134/s1070363215030251

  日期：2015.3

  A simple and convenient approach to 2-(4-aminophenyl)benzothiazole derivatives by condensation of o-aminothiophenol with (un)substituted p-aminobenzoic acid under the action of melamine formaldehyde resin (MFR) supported sulfuric acid under microwave irradiation (MW) and solvent-free conditions has been developed. Structures of the corresponding products were elucidated by IR, 1H NMR spectra, and elemental

  在三聚氰胺甲醛树脂（MFR）负载的硫酸作用下，邻位氨基硫酚与（未）取代的对氨基苯甲酸缩合，在微波辐射（MW）下，生成2-（4-氨基苯基）苯并噻唑衍生物的简便方法。已经开发出无溶剂条件。通过IR，1 H NMR光谱和元素分析来阐明相应产物的结构。该树脂可以容易地回收并再用于后续反应。
• [EN] SUBSTITUTE ISOQUINOLINES USEFUL IN THE TREATMENT OF DISEASES SUCH AS CANCER AND ATHEROSCLEROSIS<br/>[FR] ISOQUINOLINES SUBSTITUEES UTILES POUR LE TRAITEMENT DE MALADIES DU TYPE CANCER ET ATHEROSCLEROSE
  申请人：GLAXO GROUP LTD

  公开号：WO2005049576A1

  公开（公告）日：2005-06-02

  A compound of Formula (I) wherein: One of R1 and R2 is H and the other represents - NHCONHR4 wherein R4 represents a phenyl or naphthyl group (which may be optionally substituted by one or more substituents independently selected from -C1-6 alkyl, -C1-6 haloalkyl, - CH2CH2CH2-, halogen, C1-6 alkoxy, C1-6 haloalkoxy, OH, NO2), C3-7 cycloalkyl or R4 together with the NH to which it is bonded forms a morpholino group and R3 is H or NHR5 wherein R5 is H, -quinolinyl or -isoquinolinyl, -(CONH)p phenyl (wherein p is 0 or 1 and the phenyl is optionally substituted by one or more substituents independently selected from halogen, -C1-6 alkyl, -C1-6 haloalkyl, -morpholino, -SO2NH2, benzothiazole (substituted by methyl)) or a salt, solvate, or physiologically functional derivative thereof.

  根据公式(I)的化合物，其中：R1和R2之一是H，另一个代表-NHCONHR4，其中R4代表一个苯基或萘基团（可以任选地被一个或多个独立选自-C1-6烷基，-C1-6卤代烷基，-CH2CH2CH2-，卤素，C1-6烷氧基，C1-6卤代烷氧基，OH，NO2的取代基所取代），C3-7环烷基或R4与它所连接的NH形成一个吗啉基团，并且R3是H或NHR5，其中R5是H，-喹啉基或-异喹啉基，-(CONH)p苯基（其中p是0或1，并且苯基可以任选地被一个或多个独立选自卤素，-C1-6烷基，-C1-6卤代烷基，-吗啉基，-SO2NH2，苯并噻唑（被甲基取代）的取代基所取代）或其盐，溶剂化物，或生理功能衍生物。

表征谱图