3-溴-5-氯苯胺 | 96558-78-0

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-溴-5-氯苯胺
• 中文别名: 哒螨灵；3-氯-5-溴苯胺
• 英文名称: 3-bromo-5-chloroaniline
• 英文别名: 3-chloro-5-bromoaniline
• CAS: 96558-78-0
• 化学式: C₆H₅BrClN
• 分子量: 206.469
• InChiKey: YYBRLVWWPRAQDX-UHFFFAOYSA-N

物化性质

• 沸点：
  284.1±20.0 °C(Predicted)
• 密度：
  1.722±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2921420090
• 危险性防范说明：
  P301+P312+P330
• 危险性描述：
  H302
• 储存条件：
  2-8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Bromo-5-chloroaniline
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: 3-Bromo-5-chloroaniline
CAS number: 96558-78-0

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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: C6H5BrClN
Molecular weight: 206.5

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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, hydrogen bromide.

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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

应用

3-溴-5-氯苯胺是一种用于有机合成中间体和医药中间体的原料。它主要用于实验室研发过程和化工生产过程中。

制备

取2.5kg粗品3,4,5_三氟苯酚，其中甲苯含量为2%，近沸杂质中3,5_二氟苯酚含量0.05%，3,4-二氟苯酚含量0.03%，2,4-二氟苯酚含量0.025%，2,3,5-三氟苯酚含量0.07%，2,3,4-三氟苯酚含量0.042%，2,4,6-三氟苯酚含量0.01%，产品3,4,5-三氟苯酚的纯度为97.8%。

将此粗品投入5L精馏釜中，加入对叔丁基甲苯1.5kg。减压至100mmHg后进行全回流1小时。之后从塔顶以1:1的回流比收取对叔丁基甲苯馏分。收尽后，塔釜取样进行GC分析，结果显示甲苯未检出，3,5-二氟苯酚含50ppm，3,4-二氟苯酚62ppm，2,4-二氟苯酚2ppm，2,3,5-三氟苯酚3ppm，2,3,4-三氟苯酚2ppm。将此料从塔顶蒸出，得到高纯度的3,4,5-三氟苯酚2.2kg，其含量为99.98%，精馏收率为89.97%。

反应信息

• 作为反应物：
  描述：

  3-溴-5-氯苯胺 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以34%的产率得到3-bromo-4,5-dichloroaniline
  参考文献：
  名称：

  CHEMICAL COMPOUNDS

  摘要：

  该规范涉及到式（I）的化合物及其药用盐。该规范还涉及用于它们制备的过程和中间体，含有它们的药物组合物以及它们在治疗细胞增殖性疾病中的用途。

  公开号：

  US20190177338A1
• 作为产物：
  描述：

  4-硝基苯磺酸 在 盐酸 、 sodium sulfide 、 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 锌 作用下， 以 水 为溶剂， 20.0~95.0 ℃ 、2.5 MPa 条件下， 反应 2.08h， 生成 3-溴-5-氯苯胺
  参考文献：
  名称：

  一种3-氯-5-溴苯胺的合成方法

  摘要：

  本发明公开了一种3-氯-5-溴苯胺的合成方法，属于有机合成技术领域。本发明以苯磺酸为原材料，首先通过加入浓硝酸和二氧化锰催化剂生成对硝基苯磺酸，随后再通过加入NBS，生成2-溴对硝基苯磺酸，之后通过加入HCl，从而生成2-氯-6-溴对硝基苯磺酸，然后通过加入CH3COOH溶液，去除2-氯-6-溴对硝基苯磺酸中的苯磺酸，得3-氯-5-溴硝基苯，最后通过加入还原Na2S和Zn还原，从而得到本发明所制得的一种3-氯-5-溴苯胺。本实例证明，本发明制备方便简单，环保无污染，不仅设备投资少，而且无任何污染，且收率达到85％以上。

  公开号：

  CN105218379A

文献信息

• Compounds and Compositions as Protein Kinase Inhibitors
  申请人：Costales Abran Q.

  公开号：US20110052578A1

  公开（公告）日：2011-03-03

  The present invention provides compounds of Formula I or II: wherein R 1 , R 1b , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are defined herein. The compounds of Formula (I) or (II) and pharmaceutical compositions thereof are useful for the treatment of B-Raf-associated diseases.

  本发明提供了式I或II的化合物： 其中R1、R1b、R2、R3、R4、R5、R6和R7在此处定义。式(I)或(II)的化合物及其药物组合物对于治疗B-Raf相关疾病是有用的。
• [EN] COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSÉS, COMPOSITIONS ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：AQUINNAH PHARMACEUTICALS INC

  公开号：WO2020117877A1

  公开（公告）日：2020-06-11

  Herein, compounds, compositions and methods for modulating inclusion formation and stress granules in cells related to the onset of neurodegenerative diseases, musculoskeletal diseases, cancer, ophthalmological diseases, and viral infections are described.

  在这里，描述了用于调节与神经退行性疾病、肌肉骨骼疾病、癌症、眼科疾病和病毒感染相关的细胞中包涵体形成和应激颗粒的化合物、组合物和方法。
• [EN] PYRAZOLYL DERIVATIVES AS SYK INHIBITORS<br/>[FR] DÉRIVÉS DE PYRAZOLYLE EN TANT QU'INHIBITEURS DE SYK
  申请人：MERCK SHARP & DOHME

  公开号：WO2013192125A1

  公开（公告）日：2013-12-27

  The present invention provides novel pyrazole derivatives of formula I which are potent inhibitors of spleen tyrosine kinase, and are useful in the treatment and prevention of diseases mediated by said enzyme, such as asthma, COPD, rheumatoid arthritis, and cancer.

  本发明提供了一种新型的嘧啶酮衍生物，其化学式为I，它们是脾酪氨酸激酶的有效抑制剂，并且在治疗和预防由该酶介导的疾病方面具有用处，如哮喘、慢性阻塞性肺病、类风湿性关节炎和癌症。
• [EN] WDR5-MYC INHIBITORS<br/>[FR] INHIBITEURS DE WDR5-MYC
  申请人：UNIV VANDERBILT

  公开号：WO2021021951A1

  公开（公告）日：2021-02-04

  Substituted N-phenyl sulfonamide compounds inhibit WDR5-MYC interactions, and the compounds and their pharmaceutical compositions are useful for treating disorders and conditions in a subject, such as cancer cell proliferation.

  取代的N-苯基磺酰胺化合物可以抑制WDR5-MYC相互作用，这些化合物及其药物组合物可用于治疗受试者中的疾病和状况，如癌细胞增殖。
• Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds
  作者：Jakob S. Pallesen、Dilip Narayanan、Kim T. Tran、Sara M. Ø. Solbak、Giuseppe Marseglia、Louis M. E. Sørensen、Lars J. Høj、Federico Munafò、Rosa M. C. Carmona、Anthony D. Garcia、Haritha L. Desu、Roberta Brambilla、Tommy N. Johansen、Grzegorz M. Popowicz、Michael Sattler、Michael Gajhede、Anders Bach

  DOI：10.1021/acs.jmedchem.0c02094

  日期：2021.4.22

  Keap1–Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220–380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic

  靶向核因子类红细胞2相关因子2（Nrf2）和与Kelch样ECH相关蛋白1（Keap1）之间的蛋白相互作用是控制涉及氧化应激疾病的潜在治疗策略。在这里，在基于片段的解构重建（FBDR）研究中，将六类已知的小分子Keap1-Nrf2 PPI抑制剂分解为77个片段，并在四个正交试验中进行了测试。这给出了17个片段命中，其中X射线晶体学显示其中6个在Keap1 Kelch结合袋中结合。相对于亲本片段，两个命中片段以220-380倍的亲和力（K i = 16μM）被合并到化合物8中。系统优化产生了一些与K i有关的新颖类似物值0.04–0.5μM，通过X射线晶体学测定的结合模式，以及增强的微粒体稳定性。这证明了FBDR如何可用于发现新的片段片段，阐明重要的配体-蛋白质相互作用以及鉴定Keap1-Nrf2 PPI的新有效抑制剂。