2-溴-3-氟苯胺 | 111721-75-6

• 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: 2-溴-3-氟苯胺
• 英文名称: 2-bromo-3-fluoroaniline
• CAS: 111721-75-6
• 化学式: C₆H₅BrFN
• 分子量: 190.015
• InChiKey: XZRSXRUYZXBTGD-UHFFFAOYSA-N

物化性质

• 熔点：
  32-34 °C
• 沸点：
  229.8±20.0 °C(Predicted)
• 密度：
  1.670
• 闪点：
  94°(201°F)

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

• 危险等级：
  6.1
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37,S60,S9
• 危险类别码：
  R36/37/38,R22,R20/21/22,R36
• 海关编码：
  2921420090
• 危险品运输编号：
  2811
• 危险类别：
  6.1
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H302,H319
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Bromo-3-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: 2-Bromo-3-fluoroaniline
CAS number: 111721-75-6

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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: 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
UN Number: UN2810 Class: 6.1 Packing group: III
Proper shipping name: TOXIC, LIQUIDS, ORGANIC, N.O.S. OR TOXIC, LIQUIDS, ORGANIC, N.O.S. INHALA-
TION HAZARD, PACKING GROUP I, ZONE A OR B (2-Bromo-3-fluoroaniline)

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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

2-溴-3-氟苯胺主要用作有机合成和医药化学的中间体，可用于实验室研发和药物分子制备。在有机合成转化中，2-溴-3-氟苯胺中的氨基基团可以通过重氮化反应转化为重氮盐，再进行后续的卤化、氢化还原。此外，苯胺具有一定的亲核性，能与碘甲烷反应进行相应的甲基化反应。结构中的溴原子还可以通过Suzuki偶联反应在苯环的2号位连接上一个芳基。

制备

将铁粉（3当量）加入到2-溴-1-氟-3-硝基苯（1当量）中，将其置于盐酸和乙醇（盐酸与乙醇体积比为1:7）的混合溶液中。在回流条件下搅拌反应2小时（通过GC-MS监测还原进度）。反应结束后，将混合物冷却至室温，减压下除去大部分乙醇。然后用乙酸乙酯和水稀释残留物，并用1M氢氧化钠水溶液小心地中和水相，再用乙酸乙酯（3 x 15 mL）萃取水相。分离有机层并将其与合并的有机层在无水硫酸钠上干燥后过滤除去硫酸钠固体沉淀。最终得到的滤液通过减压蒸发处理，并使用硅胶柱色谱法提纯残余物，即可获得目标产物2-溴-3-氟苯胺。

反应信息

• 作为反应物：
  描述：

  2-溴-3-氟苯胺 在 亚硝酸特丁酯 、 叠氮基三甲基硅烷 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 1-Azido-2-bromo-3-fluorobenzene
  参考文献：
  名称：

  一锅点击反应合成新型含1,2,3-三唑的吡啶-吡唑酰胺衍生物及其对 根结线虫的 有效杀线虫活性评估

  摘要：

  为了找到一种新型的领先的杀线虫化合物，通过点击化学在一个反应​​罐中合成了一系列含有1,2,3-三唑的吡啶-吡唑酰胺衍生物。它们的结构通过质子核磁共振（1 H NMR），13 C NMR，19 F NMR和高分辨率质谱（HRMS）来表征。初步的生物测定表明，大多数合成的化合物在25 mg L -1的体内对 根结线虫均 表现出良好的抑制活性 。在测试的化合物中， 3a ， 3e ， 3f ， 3g ， 3j ， 3m ， 3q ， 3s ， 3t ， 3v 和 3w 表现出100％的抑制率。此外， 3k 在10 mg L -1时显示92.4％的抑制活性。这项研究表明，可以进一步优化这种含有1,2,3-三唑骨架的吡啶-吡唑酰胺，以探索新颖的，具有高生物活性的杀线虫剂。

  DOI：

  10.1007/s11164-015-2381-y
• 作为产物：
  描述：

  2-溴-3-氟苯酚 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-溴-3-氟苯胺
  参考文献：
  名称：

  2,3-二卤代苯胺的合成方法。4-功能化-1 H-吲哚的有用前体

  摘要：

  已经证明2，3-二卤代苯胺是用于合成4-卤代-1 H-吲哚的有用的起始原料。所制备的卤代吲哚的随后或原位官能化使得能够以良好的总收率获得各种2,4-或2,3,4-区域选择性官能化的吲哚。由于在文献中没有描述制备2，3-二卤代苯胺的有效合成途径，因此现在提出了制备这些1,2,3-官能化的芳族前体的不同方法。最一般的涉及从相应的2，3-二卤代苯酚的Smiles重排，并允许以直接且合成上有用的方式制备2，3-二卤代苯胺。

  DOI：

  10.1021/jo200406f

文献信息

• Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20150231142A1

  公开（公告）日：2015-08-20

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及含有上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• [EN] MACROCYCLIC INDOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'INDOLE MACROCYCLIQUES
  申请人：BROAD INST INC

  公开号：WO2019096911A1

  公开（公告）日：2019-05-23

  The present invention relates to macrocyclic indole derivatives of general formula (I), in which R1, R2, R3, R4, R5, R6, A and L are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds, and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of hyperproliferative disorders, as a sole agent or in combination with other active ingredients.

  本发明涉及通式（I）所示的大环吲哚衍生物，其中R1、R2、R3、R4、R5、R6、A和L如本文所定义，制备所述化合物的方法，用于制备所述化合物的有用中间体化合物，包含所述化合物的药物组合物和组合物，以及利用所述化合物制造用于治疗或预防疾病的药物组合物，特别是治疗过度增殖性疾病的唯一药物或与其他活性成分组合使用。
• COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES
  申请人：Van Goor Fredrick F.

  公开号：US20110098311A1

  公开（公告）日：2011-04-28

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及包含上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• Synthesis of [3.4]‐Spirooxindoles through Cascade Carbopalladation of Skipped Dienes
  作者：Hamid Azizollahi、Marta Pérez‐Gómez、Vaibhav P. Mehta、José‐Antonio García‐López

  DOI：10.1002/adsc.202000111

  日期：2020.4.27

  route to [3.4]‐spirooxindoles based on cascade carbopalladation reactions of 1,4‐dienes is described. While carbopalladation of alkenes have been used to access mainly [4.4]‐ or [4.5]‐spirocycles, 4‐exo‐trig carbopalladation has not been yet applied to the synthesis of relevant [3.4]‐spirooxindole scaffolds bearing a cyclobutyl ring. In addition, the cascade reaction generates an exocyclic double bond

  描述了基于1,4-二烯级联碳car反应的合成[3.4]-螺毒素的合成途径。虽然烯烃的碳链共轭主要用于获得[4.4]-或[4.5]-螺环，但4- exo - trig碳链共轭尚未用于合成带有环丁基环的[3.4]-螺氧并恶唑骨架。另外，级联反应产生环外双键，该环外双键可以用作进一步使螺氧并吲哚核的取代方式多样化的平台。
• [EN] BIARYL DERIVATIVES AS YAP/TAZ-TEAD PROTEIN-PROTEIN INTERACTION INHIBITORS<br/>[FR] DÉRIVÉS BIARYLE EN TANT QU'INHIBITEURS D'INTERACTION PROTÉINE-PROTÉINE YAP/TAZ-TEAD
  申请人：NOVARTIS AG

  公开号：WO2021186324A1

  公开（公告）日：2021-09-23

  The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof; (I) a method for manufacturing said compound, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition comprising said compound.

  本发明提供了化合物(I)或其药学上可接受的盐；(I)制造所述化合物的方法及其治疗用途。本发明还提供了药理活性剂的组合物和包括所述化合物的药物组合。