3-氟-4-(三氟甲基)苯硼酸 | 864759-68-2

• 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-氟-4-(三氟甲基)苯硼酸
• 英文名称: (3-fluoro-4-(trifluoromethyl)phenyl)boronic acid
• 英文别名: [3-fluoro-4-(trifluoromethyl)phenyl]boronic acid
• CAS: 864759-68-2
• 化学式: C₇H₅BF₄O₂
• mdl: MFCD08706261
• 分子量: 207.92
• InChiKey: OPDBJTGUPJBGII-UHFFFAOYSA-N

物化性质

• 沸点：
  269.8±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Fluoro-4-trifluoromethylphenylboronic acid
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-Fluoro-4-trifluoromethylphenylboronic acid
CAS number: 864759-68-2

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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: C7H5BF4O2
Molecular weight: 207.9

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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：

  3-氟-4-(三氟甲基)苯硼酸 在 甲醇 、 四(三苯基膦)钯 、 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 5-[3-Fluoro-4-(trifluoromethyl)phenyl]-4-methyl-1,2-oxazole-3-carboxylic acid
  参考文献：
  名称：

  Discovery of potent, soluble and orally active TRPV1 antagonists. Structure–activity relationships of a series of isoxazoles

  摘要：

  Systematic optimisation of a poorly soluble lead series of isoxazole-3-carboxamides was conducted. Substitution of the 4-position with specific polar functionality afforded the requisite balance of potency, solubility and physicochemical properties. Compound 21a was found to be efficacious in the rat Capsaicin Hargreaves assay following oral administration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.051
• 作为产物：
  描述：

  4-溴-2-氟三氟甲苯 、 硼酸三异丙酯 、 水 在 magnesium 、 1,2-二溴乙烷 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.6h， 以4.5 g的产率得到3-氟-4-(三氟甲基)苯硼酸
  参考文献：
  名称：

  一种联苯化合物及含有该化合物的液晶组合物及其应用

  摘要：

  本发明涉及一种联苯化合物及含有该化合物的液晶组合物及其应用。具体地，本发明公开了结构如式I所示的联苯化合物，定义详见说明书。本发明还公开了一种液晶组合物；所述液晶组合物至少包含式I化合物中的一种或多种化合物。所述液晶组合物具有改善的物理参数，例如较高的介电常数各向异性、较高的光学各向异性，较低的旋转黏度等，可实现快速响应、降低能耗和提高图像质量等优点，适用于IPS模式的液晶显示器。

  公开号：

  CN112723988A

文献信息

• [EN] PYRIDO[4,3-B]PYRAZINE-2-CARBOXAMIDES AS NEUROGENIC AGENTS FOR THE TREATMENT OF NEURODEGENERATIVE DISORDERS<br/>[FR] PYRIDO[4,3-B]PYRAZINE-2-CARBOXAMIDES UTILISÉES EN TANT QU'AGENTS NEUROGÈNES DANS LE TRAITEMENT DES TROUBLES NEURODÉGÉNÉRATIFS
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015071178A1

  公开（公告）日：2015-05-21

  The present invention relates to compounds of general formula (I), wherein R1 is hydrogen; R2 is hydrogen, lower alkyl, benzyl, lower alkyl substituted by hydroxy or is cycloalkyl optionally substituted by cyano; or R1 and R2 form together with the N-atom to which they are attached a heterocycloalkyl group, optionally containing an additional N, O or S ring atom, and which is optionally substituted by hydroxy; R3 is halogen, phenyl optionally substituted by one or more halogen, cyano, lower alkyl substituted by halogen, lower alkoxy substituted by halogen or by lower alkyl substituted by hydroxy, or is heteroaryl, optionally substituted by lower alkyl or halogen, or is 3,6-dihydro-pyran-4-yl, or is piperidin-1-yl optionally substituted by one or more halogen; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture or to it corresponding enantiomer and/or optical isomer thereof. The compounds of formula I may be used in the treatment of schizophrenia, obsessive-compulsive personality disorder, depression, bipolar disorders, anxiety disorders, normal aging, epilepsy, retinal degeneration, traumatic brain injury, spinal cord injury, post-traumatic stress disorder, panic disorder, Parkinson's disease, dementia, Alzheimer's disease, cognitive impairment, chemotherapy-induced cognitive dysfunction, Down syndrome, autism spectrum disorders, hearing loss, tinnitus, spinocerebellar ataxia, amyotrophic lateral sclerosis, multiple sclerosis, Huntington's disease, stroke, radiation therapy, chronic stress, abuse of neuro-active drugs, selected from alcohol, opiates, methamphetamine, phencyclidine and cocaine.

  本发明涉及一般式(I)的化合物，其中R1为氢；R2为氢、较低的烷基、苄基、被羟基取代的较低烷基或是环烷基，可选择地被氰基取代；或者R1和R2与它们连接的N原子一起形成一个杂环烷基基团，可选择地含有额外的N、O或S环原子，并且可选择地被羟基取代；R3为卤素、苯基，可选择地被一个或多个卤素、氰基、被卤素取代的较低烷基、被卤素取代的较低烷氧基或被羟基取代的较低烷基取代，或者是杂芳基，可选择地被较低烷基或卤素取代，或者是3,6-二氢-吡喃-4-基，或者是哌啶-1-基，可选择地被一个或多个卤素取代；或者是药学上可接受的酸加合物，或者是外消旋混合物，或者是其对应的对映体和/或光学异构体。式(I)的化合物可用于治疗精神分裂症、强迫性人格障碍、抑郁症、躁郁症、焦虑症、正常衰老、癫痫、视网膜退化、创伤性脑损伤、脊髓损伤、创伤后应激障碍、恐慌障碍、帕金森病、痴呆症、阿尔茨海默病、认知障碍、化疗引起的认知功能障碍、唐氏综合征、自闭症谱系障碍、听力丧失、耳鸣、脊髓小脑共济失调、肌萎缩侧索硬化、多发性硬化症、亨廷顿病、中风、放射治疗、慢性压力、神经活性药物滥用，从酒精、阿片类药物、甲基苯丙胺、芬太尼和可卡因中选择。
• [EN] C-MANNOSIDE COMPOUNDS USEFUL FOR THE TREATMENT OF URINARY TRACT INFECTIONS<br/>[FR] COMPOSÉS DE C-MANNOSIDE UTILES POUR LE TRAITEMENT D'INFECTIONS DES VOIES URINAIRES
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2020012336A1

  公开（公告）日：2020-01-16

  Disclosed herein are new C-mannoside compounds and compositions and their application as pharmaceuticals for the treatment of human disease. Methods of inhibition of FimH activity in a human subject are also provided for the treatment diseases such as urinary tract infection.

  本文披露了新的C-甘露糖苷化合物和组合物，以及它们作为治疗人类疾病的药物的应用。还提供了一种在人类主体中抑制FimH活性的方法，用于治疗尿路感染等疾病。
• Synthesis and biological evaluation of 4 arylcoumarin analogues as tubulin-targeting antitumor agents
  作者：Peggoty Mutai、Gilles Breuzard、Alessandra Pagano、Diane Allegro、Vincent Peyrot、Kelly Chibale

  DOI：10.1016/j.bmc.2017.01.035

  日期：2017.3

  The synthesis of twenty-six 4-arylcoumarin analogues of combretastatin A-4 (CA-4) led to the identification of two new compounds (25 and 26) with strong cytotoxic activity. Both compounds had a high cytotoxic effect on a CA-4-resistant colon adenocarcinoma cell line (HT29D4). The compounds affected cell cycle progression characterized by a mitotic block. The activity of these compounds against microtubules

  康布雷他汀A-4（CA-4）的26种4-芳基香豆素类似物的合成导致鉴定出两种具有强细胞毒活性的新化合物（25和26）。两种化合物均对耐CA-4的结肠腺癌细胞系（HT29D4）具有很高的细胞毒性作用。该化合物影响以有丝分裂阻滞为特征的细胞周期进程。检查了这些化合物在体外和细胞中对微管的活性，发现这两种化合物在体外均能有效抑制通过亚化学计量模式（如CA-4）形成微管。通过免疫荧光，观察到两种化合物均诱导强烈的微管网络破坏。我们的结果为开发针对CA-4耐药癌细胞的新型有效抗微管蛋白分子提供了有力的实验基础。
• 1,2-Diarylcyclopentenes as Selective Cyclooxygenase-2 Inhibitors and Orally Active Anti-inflammatory Agents
  作者：James J. Li、Gary D. Anderson、Earl G. Burton、J. Nita Cogburn、Joe T. Collins、Danny J. Garland、Susan A. Gregory、Horng-Chih Huang、Peter C. Isakson

  DOI：10.1021/jm00022a023

  日期：1995.10

  to be remarkably potent and selective cyclooxygenase-2 (COX-2) inhibitors. The methyl sulfone analogs 7 showed excellent COX-2 activity, with IC50s ranging from 0.003 (7f,n) to 0.87 (7o) microM. In addition, most analogs of 7 showed no activity (IC50 > 100 microM) against the COX-1 enzyme. Replacement of the methyl sulfone moiety with a sulfonamide group gave a slightly more potent (typically 2-5-fold)

  一系列的1,2-二芳基环戊烯甲基砜和磺酰胺已被证明是非常有效的选择性环氧化酶-2（COX-2）抑制剂。甲基砜类似物7具有出色的COX-2活性，IC50范围为0.003（7f，n）至0.87（7o）microM。此外，大多数7的类似物对COX-1酶均无活性（IC50> 100 microM）。用磺酰胺基团取代甲基砜部分产生的效力稍强（通常为2-5倍），但选择性较低的COX-2抑制剂，这主要是由于COX-1活性增加（20-> 100倍）。然而，在许多情况下，通过简单地在苯基的3-位引入取代基，可以提高对磺酰胺8的体外COX-1 / COX-2选择性。此外，体外选择性随取代基的大小和数量而增加，如8k（8000）> 8j（1900）> 8i（500）> 8h（100）的选择性趋势所示。更重要的是，在已建立佐剂诱发的关节炎的大鼠模型中，磺酰胺COX-2抑制剂显示出大大增强的口服活性，在1 mg时的抑制值为79
• [EN] ETHYLENE DIAMINE MODULATORS OF FATTY ACID AMIDE HYDROLASE<br/>[FR] MODULATEURS D'ÉTHYLÈNE DIAMINE D'UNE AMIDE HYDROLASE D'ACIDE GRAS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2011022348A1

  公开（公告）日：2011-02-24

  Certain ethylene diamine compounds of Formula (I) are described, which are useful as FAAH inhibitors. Such compounds may be used in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by fatty acid amide hydrolase (FAAH) activity, such as anxiety, pain, inflammation, sleep disorders, eating disorders, energy metabolism disorders, and movement disorders (e.g., multiple sclerosis). Methods of synthesizing such compounds are also disclosed.

  描述了Formula (I)中的某些乙烯二胺化合物，这些化合物可作为FAAH抑制剂。这种化合物可用于制备药物组合物，并用于治疗由脂肪酸酰胺水解酶(FAAH)活性介导的疾病状态、紊乱和情况，如焦虑、疼痛、炎症、睡眠障碍、进食障碍、能量代谢紊乱和运动障碍(例如多发性硬化)。还公开了合成这种化合物的方法。