5-氟-2-(三氟甲基)苯乙酸 | 239135-52-5

• 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: 5-氟-2-(三氟甲基)苯乙酸
• 英文名称: 2-(5-fluoro-2-(trifluoromethyl)phenyl)acetic acid
• 英文别名: 5-Fluoro-2-(Trifluoromethyl)Phenylacetic Acid；2-[5-fluoro-2-(trifluoromethyl)phenyl]acetic acid
• CAS: 239135-52-5
• 化学式: C₉H₆F₄O₂
• mdl: MFCD00236304
• 分子量: 222.139
• InChiKey: GWWZRGDMAFXULO-UHFFFAOYSA-N

物化性质

• 沸点：
  241.4±35.0℃ (760 Torr)
• 密度：
  1.436±0.06 g/cm3 (20 ºC 760 Torr)
• 闪点：
  99.8±25.9℃
• 稳定性/保质期：
  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2916399090
• 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：
  保存方法：密封于阴凉、通风干燥处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
5-Fluoro-2-(trifluoromethyl)phenylacetic 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.
5-Fluoro-2-(trifluoromethyl)phenylacetic acid
Ingredient name:
CAS number: 239135-52-5

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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: C9H6F4O2
Molecular weight: 222.1

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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：

  5-氟-2-(三氟甲基)苯乙酸 在 potassium tert-butylate 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 生成 3-(5-fluoro-2-(trifluoromethyl)phenyl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  发现口服可用的Janus激酶3选择性共价抑制剂

  摘要：

  JAK家族激酶是免疫细胞信号传导的重要介体，Janus激酶3（JAK3）长期以来一直被视为自身免疫性疾病的潜在靶标。开发高选择性JAK3抑制剂的努力已经很多年了。但是，由于JAK3对5'-三磷酸腺苷（ATP）的强烈结合偏好，许多抑制剂在酶和细胞效能之间显示出较大的差距，这阻碍了剖析JAK3在细胞环境中的作用。使用靶向共价抑制剂方法，我们发现了化合物32，该化合物克服了酶促测定中的ATP竞争（1 mM），并证明了对小鼠CTLL-2和人外周血单核细胞中JAK3依赖性信号传导的抑制活性显着提高。化合物32在JAK家族中还显示出高选择性和良好的药代动力学特性。因此，它可能是一种非常有价值的工具分子，用于研究JAK家族激酶在复杂生物学环境中的重叠作用。我们的研究还表明，对于共价激酶抑制剂，尤其是那些针对具有低K m ATP值的激酶的抑制剂，应仔细优化分子与蛋白质之间的可逆相互作用，以提高整体效能。

  DOI：

  10.1021/acs.jmedchem.8b01823

文献信息

• Direct Catalytic Enantioselective Benzylation from Aryl Acetic Acids
  作者：Patrick J. Moon、Zhongyu Wei、Rylan J. Lundgren

  DOI：10.1021/jacs.8b11390

  日期：2018.12.19

  We demonstrate that metal-catalyzed enantioselective benzylation reactions of allylic electrophiles can occur directly from aryl acetic acids. The reaction proceeds via a pathway in which decarboxylation is the terminal event, occurring after stereoselective carbon-carbon bond formation. This mechanistic feature enables enantioselective benzylation without the generation of a highly basic nucleophile

  我们证明了金属催化的烯丙基亲电试剂的对映选择性苄基化反应可以直接从芳基乙酸中发生。该反应通过其中脱羧是最终事件的途径进行，发生在立体选择性碳-碳键形成之后。这种机制特征可以实现对映选择性苄基化，而不会产生强碱性亲核试剂。因此，该过程具有广泛的官能团兼容性，这在采用已建立的协议时是不可能的。
• PYRROLO[2,3-d]PYRIMIDINE TROPOMYSIN-RELATED KINASE INHIBITORS
  申请人：Andrews Mark David

  公开号：US20120258950A1

  公开（公告）日：2012-10-11

  The present invention relates to compounds of Formula (I) and their pharmaceutically acceptable salts, wherein the substituents are as described herein, and their use in medicine, in particular as Trk antagonists.

  本发明涉及式(I)化合物及其药学上可接受的盐，其中取代基如本文所述，并且它们在医学上的用途，特别是作为Trk拮抗剂。
• MULTI-CYCLIC COMPOUNDS
  申请人：KIMURA Teiji

  公开号：US20090062529A1

  公开（公告）日：2009-03-05

  A compound represented by the formula (I): or a pharmacologically acceptable salt thereof, wherein Ar 1 represents an imidazolyl group or the like which may be substituted with a C1-6 alkyl group, Ar 2 represents a phenyl group or the like which may be substituted with a C1-6 alkoxy group, X 1 represents a double bond or the like and Het represents a triazolyl group or the like which may be substituted with a C1-6 alkyl group or the like, is effective as a therapeutic or prophylactic agent for a disease caused by Aβ.

  一种由化学式(I)表示的化合物或其药理学可接受的盐，其中Ar1代表可用C1-6烷基基团取代的咪唑基团或类似基团，Ar2代表可用C1-6烷氧基团取代的苯基团或类似基团，X1代表双键或类似基团，Het代表可用C1-6烷基基团或类似基团取代的三唑基团或类似基团，对由Aβ引起的疾病具有治疗或预防作用。
• Phosphonic Acid Analogs of Fluorophenylalanines as Inhibitors of Human and Porcine Aminopeptidases N: Validation of the Importance of the Substitution of the Aromatic Ring
  作者：Weronika Wanat、Michał Talma、Błażej Dziuk、Jean-Luc Pirat、Paweł Kafarski

  DOI：10.3390/biom10040579

  日期：——

  A library of phosphonic acid analogs of phenylalanine substituted with fluorine, chlorine and trifluoromethyl moieties on the aromatic ring was synthesized and evaluated for inhibitory activity against human (hAPN) and porcine (pAPN) aminopeptidases. Fluorogenic screening indicated that these analogs are micromolar or submicromolar inhibitors, both enzymes being more active against hAPN. In order to

  合成了在芳环上被氟，氯和三氟甲基取代的苯丙氨酸的膦酸类似物文库，并评估了其对人（hAPN）和猪（pAPN）氨基肽酶的抑制活性。荧光筛查表明，这些类似物是微摩尔或亚微摩尔抑制剂，两种酶对hAPN的活性更高。为了更好地了解最具活性的化合物的作用方式，使用了分子模型。已经证实，在所有研究的化合物中，酶的氨基膦酸部分几乎相同地结合，而活性的差异是由抑制剂的芳族侧链的位置引起的。有趣的是，单个化合物的两种对映异构体通常非常相似地结合。
• 一种JAK3选择性抑制剂
  申请人：北京大学深圳研究生院

  公开号：CN110551103B

  公开（公告）日：2022-08-23

  一种JAK3选择性抑制剂。本发明涉及一种式I/II化合物或其药学上可接受的盐，式I其中，Rh、Rg、Rf、m、Re、Rd、Ra、Rb和Rc如说明书中所定义，式II。本发明还涉及一种包括上述式I/II化合物或其药学上可接受的盐的药物组合物，以及上述式I/II化合物或上述药物组合物在制备用于治疗炎症如类风湿关节炎的药物中的用途。