3-溴-2-氟苯胺 | 58534-95-5

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯胺系列
• 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-2-氟苯胺
• 中文别名: 2-氟-3-溴苯胺；3-溴-2-氟胺
• 英文名称: 3-bromo-2-fluoroaniline
• 英文别名: 3-bromo-2-fluorobenzenamine；3-bromo-2-fluorophenylamine；2-fluoro-3-bromoaniline
• CAS: 58534-95-5
• 化学式: C₆H₅BrFN
• 分子量: 190.015
• InChiKey: HYPQOSVTIONWSN-UHFFFAOYSA-N

物化性质

• 沸点：
  228℃
• 密度：
  1.694
• 闪点：
  91℃
• pKa：
  2.13±0.10 (Predicted,Most Basic Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：
  2

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2921420090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存储条件为室温、避光且在惰性气体环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Bromo-2-fluoroaniline
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-2-fluoroaniline
CAS number: 58534-95-5

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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: C6H5BrFN
Molecular weight: 190.0

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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 fluoride, 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

用途

3-溴-2-氟苯胺可作为RIG-1激动剂用于杂三环羧酰胺的制备，以治疗细胞增殖障碍。

应用

3-溴-2-氟苯胺可用作有机合成中间体和医药中间体，主要用于实验室研发过程和化工医药合成过程中。

反应信息

• 作为反应物：
  描述：

  3-溴-2-氟苯胺 在 N-甲基吗啉 、 吡啶 、 4-二甲氨基吡啶 、 异丙基氯化镁 、 palladium diacetate 、 caesium carbonate 、 pyridinium hydrobromide perbromide 、 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 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.66h， 生成 N-{4-[4-(3-{[(2,5-difluorophenyl)sulfonyl](methoxymethyl)amino}-2-fluorophenyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-5-yl]pyridin-2-yl}acetamide
  参考文献：
  名称：

  二芳基噻唑B-Raf抑制剂的优化：鉴定具有高口服抗肿瘤活性，减轻的hERG抑制作用和低悖论效应的化合物

  摘要：

  在人类癌症中经常观察到有丝分裂原激活的蛋白激酶（MAPK）介导的途径组分RAF-MEK-ERK的异常激活，并且明显促进了肿瘤的发生。作为旨在寻找MAPK级联关键参与者B-Raf抑制剂的项目的一部分，我们最初确定了噻唑衍生物，该噻唑衍生物具有很高的效价和选择性，最佳的体外ADME特性，并且在啮齿动物中具有良好的药代动力学特征，但是患有高水平的hERG抑制活性。因此，进行了优化程序，主要集中在脚手架的R 1和R 2基团的加工上。这种努力最终导致了N-（4- {2-（1-环丙基哌啶-4-基）-4-4- [3-（2,5-二氟苯磺酰基氨基）-2-氟苯基]噻唑-5-基}-吡啶-2-基）乙酰胺（20），可保持良好的体外和体内特性，但缺乏hERG责任。除了仅对带有B-Raf V600E或V600D突变的细胞系表现出有效的抗增殖活性外，化合物20还令人感兴趣地显示，与其他已知的B-Raf抑制剂相比，非突变B

  DOI：

  10.1002/cmdc.201402424
• 作为产物：
  描述：

  2-氟-3-溴硝基苯 在 铁粉 、 氯化铵 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 以93%的产率得到3-溴-2-氟苯胺
  参考文献：
  名称：

  发现一种有效的选择性 CBP 溴结构域抑制剂 （Y08262） 治疗急性髓性白血病

  摘要：

  CREB （cyclic-AMP response element binding protein） 结合蛋白 （CBP） 的溴结构域是表观遗传学“读取器”，在转录调控中起关键作用。CBP 溴结构域被认为是急性髓性白血病 （AML） 的一个有前途的治疗靶点。在此，我们报道了一系列 1-（吲哚嗪-3-基）乙-1-酮衍生物的发现，这些衍生物是专注于提高细胞效力的有效和选择性 CBP 溴结构域抑制剂。最有前途的化合物之一 7e （Y08262） 在纳摩尔水平 （IC50 = 73.1 nM） 抑制 CBP 溴结构域，具有显著的选择性。此外，新抑制剂在 AML 细胞系中也显示出有效的抑制活性。总的来说，本研究为进一步验证 CBP 溴结构域作为 AML 药物开发的分子靶点提供了一种新的先导化合物。

  DOI：

  10.1016/j.bioorg.2023.106950

文献信息

• [EN] INHIBITORS OF KRAS G12C MUTANT PROTEINS<br/>[FR] INHIBITEURS DE PROTÉINES MUTANTES KRAS G12C
  申请人：ARAXES PHARMA LLC

  公开号：WO2017058915A1

  公开（公告）日：2017-04-06

  Compounds having activity as inhibitors of G12C mutant KRAS protein are provided. The compounds have the following structure (I): or a pharmaceutically acceptable salt, tautomer, stereoisomer or prodrug thereof, wherein A, B R1, R2a, R2b, R3a, R3b, R4a, R4b, G1, G2, m1, m2, L1, L2 and E are as defined herein. Methods associated with preparation and use of such compounds, pharmaceutical compositions comprising such compounds and methods to modulate the activity of G12C mutant KRAS protein for treatment of disorders, such as cancer, are also provided.

  提供了作为G12C突变KRAS蛋白抑制剂活性的化合物。这些化合物具有以下结构（I）：或其药用可接受的盐、互变异构体、立体异构体或前药，其中A、B、R1、R2a、R2b、R3a、R3b、R4a、R4b、G1、G2、m1、m2、L1、L2和E如本文所定义。还提供了与制备和使用这些化合物相关的方法，包括包含这些化合物的药物组合物以及调节G12C突变KRAS蛋白活性的方法，用于治疗癌症等疾病。
• CONJUGATES OF CEREBLON BINDING COMPOUNDS AND G12C MUTANT KRAS, HRAS OR NRAS PROTEIN MODULATING COMPOUNDS AND METHODS OF USE THEREOF
  申请人：Araxes Pharma LLC

  公开号：US20180015087A1

  公开（公告）日：2018-01-18

  Conjugates of a cereblon-binding compound and compounds having modulatory activity against G12C mutant KRAS, HRAS or NRAS G12C proteins are provided. Methods associated with preparation and use of such conjugates, pharmaceutical compositions comprising such conjugates and methods to modulate the activity of G12C mutant KRAS, HRAS or NRAS G12C proteins for treatment of disorders, such as cancer, are also provided.

  提供了与谷氨酰脑结合化合物和具有调节活性对抗G12C突变KRAS、HRAS或NRAS G12C蛋白的化合物的共轭物。还提供了与制备和使用这种共轭物相关的方法，包括含有这种共轭物的药物组合物以及调节G12C突变KRAS、HRAS或NRAS G12C蛋白活性的方法，用于治疗癌症等疾病。
• Ambipolar Polymer Field-Effect Transistors Based on Fluorinated Isoindigo: High Performance and Improved Ambient Stability
  作者：Ting Lei、Jin-Hu Dou、Zhi-Jun Ma、Cong-Hui Yao、Chen-Jiang Liu、Jie-Yu Wang、Jian Pei

  DOI：10.1021/ja310283f

  日期：2012.12.12

  Ambipolar transport behavior in isoindigo-based conjugated polymers is observed for the first time. Fluorination on the isoindigo unit effectively lowers the LUMO level of the polymer and significantly increases the electron mobility from 10(-2) to 0.43 cm(2) V(-1) s(-1) while maintaining high hole mobility up to 1.85 cm(2) V(-1) s(-1) for FET devices fabricated in ambient. Further investigation indicates

  首次观察到基于异靛蓝的共轭聚合物的双极性传输行为。异靛蓝单元上的氟化有效地降低了聚合物的 LUMO 水平，并显着增加了电子迁移率从 10(-2) 到 0.43 cm(2) V(-1) s(-1)，同时保持高达 1.85 cm 的高空穴迁移率(2) V(-1) s(-1) 对于在环境中制造的 FET 器件。进一步的研究表明，氟化也会影响聚合物主链的链间相互作用，从而导致薄膜中不同的聚合物堆积。
• [EN] METHODS AND COMPOSITIONS FOR INHIBITION OF RAS<br/>[FR] MÉTHODES ET COMPOSITIONS PERMETTANT L'INHIBITION DE LA RAS
  申请人：ARAXES PHARMA LLC

  公开号：WO2016049568A1

  公开（公告）日：2016-03-31

  Inhibitors of Ras protein, methods to modulate the activity of Ras protein, and methods of treatment of disorders mediated by Ras protein are provided. A method for regulating activity of a K-Ras, H-Ras or N-Ras mutant protein with a compound is described. Disorders that can be treated include cancer, such as hematological cancer, pancreatic cancer, MYH associated polyposis, colorectal cancer, or lung cancer.

  提供了Ras蛋白的抑制剂，调节Ras蛋白活性的方法，以及通过Ras蛋白介导的疾病治疗方法。描述了一种使用化合物调节K-Ras、H-Ras或N-Ras突变蛋白活性的方法。可治疗的疾病包括癌症，如血液癌症、胰腺癌、MYH相关性息肉症、结直肠癌或肺癌。
• [EN] INHIBITORS OF KRAS G12C<br/>[FR] INHIBITEURS DE K-RAS G12C
  申请人：ARAXES PHARMA LLC

  公开号：WO2015054572A1

  公开（公告）日：2015-04-16

  Compounds having activity as inhibitors of G12C mutant KRAS protein are provided. The compounds have the following structure (I): or a pharmaceutically acceptable salt, tautomer, prodrug or stereoisomer thereof, wherein R1, R2a, R3a, R3b, R4a, R4b, G1, G2, L1, L2, m1, m2, A, B, W, X, Y, Z and E are as defined herein. Methods associated with preparation and use of such compounds, pharmaceutical compositions comprising such compounds and methods to modulate the activity of G12C mutant KRAS protein for treatment of disorders, such as cancer, are also provided.

  提供了作为G12C突变KRAS蛋白抑制剂活性的化合物。这些化合物具有以下结构（I）：或其药用可接受的盐、互变异构体、前药或立体异构体，其中R1、R2a、R3a、R3b、R4a、R4b、G1、G2、L1、L2、m1、m2、A、B、W、X、Y、Z和E如本文所定义。还提供了与制备和使用这些化合物相关的方法，包括含有这些化合物的药物组合物以及调节G12C突变KRAS蛋白活性以治疗癌症等疾病的方法。