2-溴-5-三氟甲基苯甲酸 | 1483-56-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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-5-三氟甲基苯甲酸
• 英文名称: 2-bromo-5-(trifluoromethyl)benzoic acid
• CAS: 1483-56-3
• 化学式: C₈H₄BrF₃O₂
• mdl: MFCD06208253
• 分子量: 269.018
• InChiKey: REBQGRPKXYIJDC-UHFFFAOYSA-N

物化性质

• 熔点：
  116-117℃
• 沸点：
  301.0±42.0 °C(Predicted)
• 密度：
  1.773

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2916399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Bromo-5-(trifluoromethyl)benzoic acid
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
2-Bromo-5-(trifluoromethyl)benzoic acid
Ingredient name:
CAS number: 1483-56-3

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H4BrF3O2
Molecular weight: 269.0

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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, 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

2-溴-5-三氟甲基苯甲酸是一种有机中间体，可通过以下步骤制备。首先，从4-溴-三氟甲苯出发，进行碘代反应生成1-溴-2-碘-4-三氟甲基苯；接着，通过进一步的化学转化即可得到目标产物。

制备

在冰浴冷却至-78℃的情况下，将2,2,6,6-四甲基六氢哌啶（22.5毫升，133.4毫摩尔）滴加到正丁基锂（正-BuLi，2.5M的四氢呋喃THF溶液，66.7毫摩尔）中，再将此混合物加入到130毫升THF溶剂中。搅拌30分钟后，在氮气保护下缓慢冷却至-100℃。随后，分批小心地滴加纯净的1-溴-4-(三氟甲基)苯（15克，66.7毫摩尔），并在-100℃下反应6小时。

将此混合物倒在新鲜制备的碎干冰上，并在室温下搅拌过夜。蒸馏除去溶剂后，用150毫升水稀释并进行乙醚萃取（每次使用50毫升共三次）。再用水层中加入浓盐酸酸化并使用二氯甲烷进行萃取（每次50毫升共三次）提取有机相。合并的有机层经饱和氯化钠溶液洗涤，用硫酸镁干燥、过滤，并浓缩得到白色固体2-溴-5-三氟甲基苯甲酸（产率约21%）。通过核磁共振氢谱分析（1H NMR，300MHz，氯仿-d）确认产物结构，其计算值与实测值吻合：δ 7.7 (dd, J＝8.4, 2.3 Hz)；7.9 (d, J＝8.4 Hz)；8.3 (d, J＝2.0 Hz)，质谱（ES+）测定值为266.7，理论值为267.93。

反应信息

• 作为反应物：
  描述：

  2-溴-5-三氟甲基苯甲酸 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以96%的产率得到2-溴-5-三氟甲基苄醇
  参考文献：
  名称：

  二芳基碘分子间多米诺反应涉及两个C ？H功能化

  摘要：

  据报道，钯催化的两个芳基碘化物的分子间交叉偶联使多环系统具有较高的收敛性和效率。

  DOI：

  10.1002/anie.201400807
• 作为产物：
  描述：

  3-氟-5-甲氧基苯甲醛 在 氧气 、 Langlois reagent 作用下， 以 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以92%的产率得到2-溴-5-三氟甲基苯甲酸
  参考文献：
  名称：

  光和氧使能的三氟甲烷亚磺酸钠介导的C–H键的选择性氧化

  摘要：

  可见光诱导的有机反应是有机化学中重要的化学转化，其效率在很大程度上取决于合适的光催化剂。但是，常用的光催化剂是贵重的过渡金属配合物和精细的有机染料，由于成本高而阻碍了大规模生产。在这里，我们首次报道了一种新的策略：光和氧使能的三氟甲亚磺酸钠介导的C–H键的选择性氧化，使高附加值的芳族酮和羧酸易于在高-使用现成的烷基芳烃，甲基芳烃和醛作为原料，收率极高。机理研究表明，在光的照射下用氧气处理廉价且容易获得的三氟甲烷亚磺酸钠可以原位形成五配位硫化物中间体，作为有效的光敏剂。该方法代表了一种高效，经济和环境友好的策略，并且光和氧气使能的三氟甲烷亚磺酸钠光催化体系代表了光化学领域的突破。

  DOI：

  10.1039/d0gc00383b

文献信息

• COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS
  申请人：Carroll William A.

  公开号：US20100249129A1

  公开（公告）日：2010-09-30

  Disclosed herein are compounds of formula (I) wherein Ring A and R 1 are as defined in the specification. Pharmaceutical compositions comprising such compounds, and methods for treating conditions and disorders using such compounds and pharmaceutical compositions are also disclosed.

  本文揭示了以下式(I)的化合物 其中环A和R 1 如规范中所定义。还披露了包含这些化合物的药物组合物，以及使用这些化合物和药物组合物治疗疾病和疾病的方法。
• Dibenzyl Amine Compounds and Derivatives
  申请人：Chang George

  公开号：US20070213371A1

  公开（公告）日：2007-09-13

  Dibenzyl amine compounds and derivatives, pharmaceutical compositions containing such compounds and the use of such compounds to elevate certain plasma lipid levels, including high density lipoprotein-cholesterol and to lower certain other plasma lipid levels, such as LDL-cholesterol and triglycerides and accordingly to treat diseases which are exacerbated by low levels of HDL cholesterol and/or high levels of LDL-cholesterol and triglycerides, such as atherosclerosis and cardiovascular diseases in some mammals, including humans.

  二苯基胺化合物及其衍生物，含有这种化合物的药物组合物以及使用这种化合物提高某些血浆脂质水平，包括高密度脂蛋白胆固醇，并降低其他一些血浆脂质水平，如低密度脂蛋白胆固醇和甘油三酯，并据此治疗由高密度脂蛋白胆固醇水平低和/或低密度脂蛋白胆固醇和甘油三酯水平高加重的疾病，如动脉粥样硬化和心血管疾病在某些哺乳动物，包括人类。
• FLAP MODULATORS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：US20150259357A1

  公开（公告）日：2015-09-17

  The present invention relates to compounds of Formula (I), or a form thereof, wherein ring A, R 1 , R 2 , R 3 , R 3 ′, L, W, and V are as defined herein, useful as FLAP modulators. The invention also relates to pharmaceutical compositions comprising compounds of Formula (I). Methods of making and using the compounds of Formula (I) are also within the scope of the invention

  本发明涉及式（I）的化合物，或其形式，其中环A，R1，R2，R3，R3'，L，W和V如本文所定义，可用作FLAP调节剂。该发明还涉及包含式（I）化合物的药物组合物。制备和使用式（I）化合物的方法也属于本发明的范围。
• PIPERAZINE CARBAMATES AND METHODS OF MAKING AND USING SAME
  申请人：ABIDE THERAPEUTICS, INC.

  公开号：US20190202801A1

  公开（公告）日：2019-07-04

  Provided herein are piperazine carbamates and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful as modulators of MAGL and/or ABHD6. Furthermore, the subject compounds and compositions are useful for the treatment of pain.

  本文提供了哌嗪氨基甲酸酯和包含该化合物的药物组合物。所述化合物和组合物可用作MAGL和/或ABHD6的调节剂。此外，所述化合物和组合物可用于治疗疼痛。
• [EN] 2,3-DIHYDROQUINAZOLIN COMPOUNDS AS NAV1.8 INHIBITORS<br/>[FR] COMPOSÉS 2,3-DIHYDROQUINAZOLINE EN TANT QU'INHIBITEURS DE NAV1.8
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2020261114A1

  公开（公告）日：2020-12-30

  The present invention relates to Nav1.8 Inhibitor 2,3-dihydroquinazolin compounds of Formula (X); wherein Y', X', B', R1', R2', R3', R5', R6', R7', and z1 are as defined herein; or pharmaceutically acceptable salts or tautomer forms thereof, corresponding pharmaceutical compositions or formulations, methods or processes of compound preparation, methods, compounds for use in, uses for and/or combination therapies for treating pain and/or pain-related or associated disease(s), disorder(s) or condition(s), respectively.

  本发明涉及Nav1.8抑制剂2,3-二氢喹唑啉化合物，其化学公式为(X)；其中Y'、X'、B'、R1'、R2'、R3'、R5'、R6'、R7'和z1如本文所述定义；或其药用可接受的盐或互变异构体形式，相应的药物组合物或制剂，化合物制备的方法或过程，方法，化合物用于，用于治疗疼痛和/或与疼痛相关的或相关的疾病、失调或状况的使用和/或联合治疗方法。