3-氰基-5-(三氟甲基)苯基硼酸 | 1212021-62-9

• 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-氰基-5-(三氟甲基)苯基硼酸
• 英文名称: (3-cyano-5-(trifluoromethyl)phenyl)boronic acid
• 英文别名: [3-cyano-5-(trifluoromethyl)phenyl]boronic acid
• CAS: 1212021-62-9
• 化学式: C₈H₅BF₃NO₂
• 分子量: 214.939
• InChiKey: CTJAWCWPRYNDDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  335.4±52.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.26
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.2
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312+P330,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Cyano-5-(trifluoromethyl)phenylboronic acid
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
Avoid breathing dust/fume/gas/mist/vapours/spray
P261:
P280: Wear protective gloves/protective clothing/eye protection/face protection
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.
Ingredient name: 3-Cyano-5-(trifluoromethyl)phenylboronic acid
CAS number: 1212021-62-9

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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.
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
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H5BF3NO2
Molecular weight: 214.9

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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, nitrogen oxides, 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-氰基-5-(三氟甲基)苯基硼酸 、 methyl 4-bromo-1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-3-methyl-1H-pyrazole-5-carboxylate 在 四(三苯基膦)钯 、 sodium carbonate 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 甲醇 为溶剂， 生成 4-(3-cyano-5-(trifluoromethyl)phenyl)-1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-3-methyl-1H-pyrazole-5-carboxylic acid
  参考文献：
  名称：

  1-噻唑-2-基-N-3-甲基-1H-吡唑-5-羧酸衍生物作为抗肿瘤药

  摘要：

  发现一类取代的1-噻唑-2-基-N-3-甲基-1H-吡咯-5-羧酸衍生物对多种肿瘤细胞系具有有效的抗增殖活性。此类化合物（14）在广泛的血液学和实体瘤癌细胞系中进行了分析，证明其在G0 / G1间期具有细胞周期停滞，并且对不同类型的精选癌细胞具有强大的抗增殖活性没有观察到对正常人细胞的影响。一个例子是对人B细胞淋巴瘤细胞系（BJAB）的选择性抑制。化合物14是口服生物利用的，并且在小鼠中耐受性良好。讨论了这一系列化合物的合成和结构活性关系（SAR）。

  DOI：

  10.1016/j.bmcl.2017.08.003

文献信息

• HTS followed by NMR based counterscreening. Discovery and optimization of pyrimidones as reversible and competitive inhibitors of xanthine oxidase
  作者：Johan Evenäs、Fredrik Edfeldt、Matti Lepistö、Naila Svitacheva、Anna Synnergren、Britta Lundquist、Mia Gränse、Anna Rönnholm、Mikael Varga、John Wright、Min Wei、Sherrie Yue、Junfeng Wang、Chong Li、Xuan Li、Gang Chen、Yong Liao、Gang Lv、Ann Tjörnebo、Frank Narjes

  DOI：10.1016/j.bmcl.2014.01.050

  日期：2014.3

  based inhibitors of xanthine oxidase is described. After a high-throughput screening campaign, an NMR based counterscreen was used to distinguish actives, which interact with XO in a reversible manner, from assay artefacts. This approach identified pyrimidone 1 as a reversible and competitive inhibitor with good lead-like properties. A hit to lead campaign gave compound 41, a nanomolar inhibitor of hXO

  描述了新型，非嘌呤的黄嘌呤氧化酶抑制剂的鉴定。经过高通量筛选活动后，基于NMR的反筛选用于区分活性物，这些活性物以可逆方式与XO相互作用，与分析伪像分离。该方法将嘧啶酮1鉴定为可逆的竞争性抑制剂，具有良好的铅样性质。导致先头运动获得化合物41，一种hXO的纳摩尔抑制剂，口服给药后在高尿酸血症大鼠模型中具有功效。
• Discovery of Orally Bioavailable FmlH Lectin Antagonists as Treatment for Urinary Tract Infections
  作者：Amarendar Reddy Maddirala、Kevin Tamadonfar、Jerome S. Pinkner、Denise Sanick、Scott J. Hultgren、James W. Janetka

  DOI：10.1021/acs.jmedchem.3c02128

  日期：2024.3.14
• WO2023/61263
  申请人：——

  公开号：——

  公开（公告）日：——
• 1-Thiazol-2-yl-N-3-methyl-1H-pyrozole-5-carboxylic acid derivatives as antitumor agents
  作者：Alan B. Cooper、Stephane Ciblat、Gerald Shipps、Jedd Levine、Matthew Kostura、Vibha Oza、Lea Constantineau-Forget、Martin Dery、Chantal Grand-Maitre、Nicolas Bruneau-Latour、Edith Bellavance、Michael Patane、Arshad Siddiqui、Michael Luther

  DOI：10.1016/j.bmcl.2017.08.003

  日期：2017.9

  A class of substituted 1-thiazol-2-yl-N-3-methyl-1H-pyrozole-5-carboxylic acid derivatives was found to have potent anti-proliferative activity against a broad range of tumor cell lines. A compound from this class (14) was profiled across a broad panel of hematologic and solid tumor cancer cell lines demonstrating cell cycle arrest at the G0/G1 interphase and has potent anti-proliferative activity

  发现一类取代的1-噻唑-2-基-N-3-甲基-1H-吡咯-5-羧酸衍生物对多种肿瘤细胞系具有有效的抗增殖活性。此类化合物（14）在广泛的血液学和实体瘤癌细胞系中进行了分析，证明其在G0 / G1间期具有细胞周期停滞，并且对不同类型的精选癌细胞具有强大的抗增殖活性没有观察到对正常人细胞的影响。一个例子是对人B细胞淋巴瘤细胞系（BJAB）的选择性抑制。化合物14是口服生物利用的，并且在小鼠中耐受性良好。讨论了这一系列化合物的合成和结构活性关系（SAR）。