4'-(三氟甲基)双苯基-3-羧酸 | 199528-28-4

• 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: 4'-(三氟甲基)双苯基-3-羧酸
• 中文别名: 4'-三氟甲基[1,1'-联苯]-3-羧酸；4-三氟甲基-联苯-3-羧酸；4'-(三氟甲基)双苯基-3-羧酸,97%
• 英文名称: 4'-(trifluoromethyl)[1,1'-biphenyl]-3-carboxylic acid
• 英文别名: 3-(4-trifluoromethylphenyl)-benzoic acid；4'-Trifluoromethyl-biphenyl-3-carboxylic acid；3-[4-(trifluoromethyl)phenyl]benzoic acid
• CAS: 199528-28-4
• 化学式: C₁₄H₉F₃O₂
• mdl: MFCD03424604
• 分子量: 266.219
• InChiKey: BJKGBAVGLRYCTK-UHFFFAOYSA-N

物化性质

• 沸点：
  377.5±42.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)
• 溶解度：
  碱性溶液（微溶）、DMSO（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R22
• 海关编码：
  2916399090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4’-(Trifluoromethyl)biphenyl-3-carboxylic 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.
4’-(Trifluoromethyl)biphenyl-3-carboxylic acid
Ingredient name:
CAS number: 199528-28-4

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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: C14H9F3O2
Molecular weight: 266.2

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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.

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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

反应信息

• 作为反应物：
  描述：

  4'-(三氟甲基)双苯基-3-羧酸 在 sodium tetrahydroborate 、 二溴亚砜 、 三氟化硼四氢呋喃络合物 、 硼酸三甲酯 、 potassium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 24.8h， 生成 sodium (S)-3-(4-{[4'-(trifluoromethyl)biphenyl-3-yl]methoxy}phenyl)hex-4-ynoate
  参考文献：
  名称：

  GPR40受体激动剂的可扩展合成方法的开发

  摘要：

  描述了新型GPR40受体激动剂AMG 837的早期工艺开发和盐选择。合成AMG 837的途径涉及两个关键片段（S）-3-（4-羟苯基）己-4-炔酸（1）和3-（溴甲基）-4'-（三氟甲基）的收敛合成和偶联联苯（2）。通过经典拆分相应的外消旋酸（±）-1，以35％的总收率制备了手性β-炔酸1。（±）-1的有效和可扩展合成是通过伸缩的反应序列实现的，包括从3中制备的就地保护的麦德鲁姆酸衍生受体的共轭炔基化反应。联芳基溴化物2是通过2步Suzuki-Miyaura偶联-溴化序列制备的，收率为86％。由氢氧化四丁基phosph介导的化学选择性苯酚烷基化可将1和2直接偶联，得到AMG837。由于原料药的游离酸形式的理化稳定性差，因此选择了钠盐形式用于早期开发，并且更稳定，随后形成结晶的半钙盐二水合物形式。总体而言，AMG 837的原始12步合成被9步稳健的路线所取代，从而以25％的收率提供了目标。

  DOI：

  10.1021/op1003055
• 作为产物：
  描述：

  4-(三氟甲基)-[1,1-联苯]-3-羧酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 4'-(三氟甲基)双苯基-3-羧酸
  参考文献：
  名称：

  发现含有联苯药效团的新型甲酰胺衍生物作为用于抗性管理的潜在杀菌剂

  摘要：

  天然产物是药物和农用化学品发现的主要来源之一。联苯骨架是许多天然产物中普遍存在的结构，具有广泛的生物活性。因此，为了研究天然联苯衍生物的潜在应用，基于天然联苯木脂素的活性药效团，设计并合成了一系列具有不同取代基模式的新型甲酰胺衍生物，及其对几种典型植物病原体的体外抗真菌活性。对卵菌纲、子囊菌纲、半知菌纲和担子菌纲进行了全面研究。这些极具潜力的化合物在针对灰葡萄孢的体内试验中得到了进一步测试。通过对黄瓜的研究，证明其在防治常见植物病害方面的实际应用，表明四种化合物可以有效防治多菌灵、芦他霉素和吡唑烷等抗性菌株。还利用分子对接、显微技术和无标记定量蛋白质组学分析探索了化合物B12对抗灰霉病的潜在作用模式。结果表明，化合物B12可能是一种潜在的用于控制灰霉病抗性的新型杀菌剂，它可以影响灰霉病菌的蛋白质合成。这些发现可为开发新型联苯衍生物作为潜在的绿色抗真菌剂提供一定的理论基础。

  DOI：

  10.1021/acs.jafc.3c04307
• 作为试剂：
  描述：

  4-三氟甲基苯硼酸 、 间溴苯甲酸 、 disodium;carbonate 在 钯 disodium;carbonate 、 水 、 4'-(三氟甲基)双苯基-3-羧酸 作用下， 以 Water isopropylalcohol 为溶剂， 反应 4.0h， 生成 4'-(三氟甲基)双苯基-3-羧酸
  参考文献：
  名称：

  Compounds, pharmaceutical compositions and methods for use in treating metabolic disorders

  摘要：

  本发明提供了一些有用的化合物，例如用于调节受试者胰岛素水平的化合物，其具有一般式Q-L1-P-L2-M-X-L3-A，其中变量Q、L1、P、L2、M、X、L3和A的定义在此处给出。本发明还提供了该化合物的组成和使用方法，例如用于治疗II型糖尿病。

  公开号：

  US07816367B2

文献信息

• Production methods of alpha, alpha, alpha-trifluoromethylphenyl-substituted benzoic acid and intermediate therefor
  申请人：——

  公开号：US20010020110A1

  公开（公告）日：2001-09-06

  The present invention relates to a production method of compound [V] useful as an intermediate for medicaments and agrochemicals. The method includes reacting compound [III] with hexamethylenetetramine under heating to give compound [IV], and oxidizing the obtained compound [IV] with a halous acid salt or a ruthenium compound. According to the present invention, moreover, an organometallic compound having a tolyl group and compound [I] are cross-coupled in the presence of a catalyst to give compound [II] useful as an intermediate for medicaments and agrochemicals. The compound [II] is halogenated to give compound [III]. 1 wherein X is halogen atom.

  本发明涉及一种用作医药和农药中间体的化合物[V]的生产方法。该方法包括在加热下将化合物[III]与六甲基四胺反应以得到化合物[IV]，以及用卤素酸盐或钌化合物氧化所得到的化合物[IV]。根据本发明，另外，在催化剂存在下，将具有甲苯基的有机金属化合物与化合物[I]进行交叉偶联以得到用作医药和农药中间体的化合物[II]。化合物[II]被卤素化以得到化合物[III]。 1 其中X是卤素原子。
• PIPERIDIN-4-YL-AZETIDINE DIAMIDES AS MONOACYLGLYCEROL LIPASE INHIBITORS
  申请人：Connolly Peter J.

  公开号：US20130102584A1

  公开（公告）日：2013-04-25

  Disclosed are compounds, compositions and methods for treating various diseases, syndromes, conditions and disorders, including pain. Such compounds, and enantiomers, diastereomers, and pharmaceutically acceptable salts thereof, are represented by Formula (I) as follows: wherein Y, Z, and R are defined herein.

  揭示了用于治疗各种疾病、综合症、症状和障碍的化合物、组合物和方法，包括疼痛。这些化合物及其对映体、二对映体和其药用可接受盐如下所示： 其中Y、Z和R在此处定义。
• DI-AZETIDINYL DIAMIDE AS MONOACYLGLYCEROL LIPASE INHIBITORS
  申请人：Connolly Peter J.

  公开号：US20120058986A1

  公开（公告）日：2012-03-08

  Disclosed are compounds, compositions and methods for treating various diseases, syndromes, conditions and disorders, including pain. Such compounds are represented by Formula (I) as follows: wherein Q and Z are defined herein.

  揭示了用于治疗各种疾病、综合症、症状和障碍的化合物、组合物和方法，包括疼痛。这些化合物由以下式（I）表示： 其中Q和Z在此处定义。
• Compounds, pharmaceutical compositions and methods for their use in treating metabolic disorders
  申请人：Houze Jonathan

  公开号：US20060270724A1

  公开（公告）日：2006-11-30

  The present invention provides compounds useful, for example, for modulating insulin levels in a subject, having the general formula I: wherein Q is an optionally substituted phenyl; L is a bond or O; P is a benzene or an optionally substituted thiazole ring; and R 1 has the values provided herein. The present invention also provides compositions, uses, and methods for use of the compounds, for instance, for treatment of type II diabetes.

  本发明提供了一种化合物，例如，用于调节受试者体内胰岛素水平，其具有一般式I： 其中Q是可选择取代的苯基；L是键或O；P是苯环或可选择取代的噻唑环；R1具有此处提供的值。本发明还提供了所述化合物的组合物、用途和使用方法，例如，用于治疗2型糖尿病。
• OXOPIPERAZINE-AZETIDINE AMIDES AND OXODIAZEPINE-AZETIDINE AMIDES AS MONOACYLGLYCEROL LIPASE INHIBITORS
  申请人：Connolly Peter J.

  公开号：US20120077797A1

  公开（公告）日：2012-03-29

  Disclosed are compounds, compositions and methods for treating various diseases, syndromes, conditions and disorders, including pain. Such compounds, and enantiomers, diastereomers, and pharmaceutically acceptable salts thereof, are represented by Formula (Ia) and Formula (Ib) as follows: wherein Y, Z, and n are defined herein; and wherein Y b and Z b are as defined herein.

  本文披露了用于治疗各种疾病、综合症、状况和障碍，包括疼痛的化合物、组合物和方法。这些化合物及其对映体、二对映体和药学上可接受的盐由以下的化学式(Ia)和化学式(Ib)表示：其中Y、Z和n在此定义；以及其中Yband Zbare如此定义。