5-羧基-2-氟苯硼酸 | 874219-59-7

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯硼酸系列
• 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-羧基-2-氟苯硼酸
• 中文别名: 5-羧基-2-氟苯基硼酸；2-氟-5-羧基苯硼酸
• 英文名称: 3-borono-4-fluorobenzoic acid
• 英文别名: 5-Carboxy-2-fluorophenylboronic acid
• CAS: 874219-59-7
• 化学式: C₇H₆BFO₄
• mdl: MFCD08436065
• 分子量: 183.932
• InChiKey: YLZPFWJYAFZZHF-UHFFFAOYSA-N

物化性质

• 熔点：
  224-226
• 沸点：
  432.9±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT, KEEP COLD
• 危险品标志：
  Xi
• 海关编码：
  2931900090
• 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
5-Carboxy-2-fluorophenylboronic acid
Product Name:
Synonyms: 3-Borono-4-fluorobenzoic acid

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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-Carboxy-2-fluorophenylboronic acid
Ingredient name:
CAS number: 874219-59-7

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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: C7H6BFO4
Molecular weight: 183.9

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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：

  5-羧基-2-氟苯硼酸 在 四(三苯基膦)钯 、 palladium diacetate 、 caesium carbonate 、 sodium hydroxide 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 32.0h， 生成 4-Fluoro-3-[2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(3,3,3-trifluoropropyl)furo[2,3-b]pyridin-5-yl]benzoic acid
  参考文献：
  名称：

  CYANO CONTAINING AZABENZOFURAN COMPOUNDS FOR THE TREATMENT OF HEPATITIS C

  摘要：

  公式I的化合物，包括它们的盐，以及使用这些化合物的组合物和方法已经列出。这些化合物对丙型肝炎病毒（HCV）具有活性，并可能对感染HCV的人有治疗作用。

  公开号：

  US20150266886A1
• 作为产物：
  描述：

  3-溴-4-氟苯甲酸 、 正丁基锂 、 硼酸三异丙酯 、 在 乙酸乙酯 、 盐酸 、 Brine 、 magnesium sulfate 作用下， 以 四氢呋喃 、 盐酸 为溶剂， 反应 21.25h， 生成 5-羧基-2-氟苯硼酸
  参考文献：
  名称：

  Hetero-bridge substituted 8-arylquinoline pde4 inhibitors

  摘要：

  8-芳基喹啉，其中8-位置的芳基基团含有一个或两个原子桥连接到苯基，5或6成员杂环芳基或融合的双环杂环芳基基团，并且至少一个桥接原子不是碳，是PDE4抑制剂。

  公开号：

  US07144896B2

文献信息

• [EN] COMPOUNDS FOR THE TREATMENT OF HEPATITIS C<br/>[FR] COMPOSÉS POUR LE TRAITEMENT DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2010030592A1

  公开（公告）日：2010-03-18

  The disclosure provides compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds have activity against hepatitis C virus (HCV) and may be useful in treating those infected with HCV.

  本公开提供了公式I的化合物，包括它们的盐，以及使用这些化合物的组合物和方法。这些化合物对丙型肝炎病毒（HCV）具有活性，可能对治疗HCV感染者有益。
• BICYCLIC HETEROCYCLES AS FGFR INHIBITORS
  申请人：Incyte Corporation

  公开号：US20210214366A1

  公开（公告）日：2021-07-15

  The present disclosure relates to bicyclic heterocycles, and pharmaceutical compositions of the same, that are inhibitors of the FGFR enzyme and are useful in the treatment of FGFR-associated diseases such as cancer.

  本公开涉及双环杂环化合物及其药物组合物，这些化合物是FGFR酶的抑制剂，可用于治疗FGFR相关疾病，如癌症。
• [EN] COMPOUNDS FOR THE TREATMENT OF HEPATITIS C<br/>[FR] COMPOSÉS UTILISABLES POUR LE TRAITEMENT DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011112191A1

  公开（公告）日：2011-09-15

  The disclosure provides compounds of formula (I), including their salts, as well as compositions and methods of using the compounds. The compounds have activity against hepatitis C virus (HCV) and may be useful in treating those infected with HCV.

  本公开提供了公式(I)的化合物，包括它们的盐，以及使用这些化合物的组合物和方法。这些化合物对丙型肝炎病毒(HCV)具有活性，可能对治疗HCV感染者有益。
• Fast and Tight Boronate Formation for Click Bioorthogonal Conjugation
  作者：Burcin Akgun、Dennis G. Hall

  DOI：10.1002/anie.201510321

  日期：2016.3.14

  A new click bioorthogonal reaction system was devised to enable the fast ligation (kON≈340 m−1 s−1) of conjugatable derivatives of a rigid cyclic diol (nopoldiol) and a carefully optimized boronic acid partner, 2‐methyl‐5‐carboxymethylphenylboronic acid. Using NMR and fluorescence spectroscopy studies, the corresponding boronates were found to form reversibly within minutes at low micromolar concentration

  新的点击生物正交反应系统设计成使快速连接（ķ ON ≈340 米-1 小号-1）一个刚性的环状二醇（nopoldiol）和仔细优化硼酸伙伴的缀合衍生物，2-甲基-5-羧甲基苯基硼酸。使用NMR和荧光光谱研究，发现对应于硼酸酯在水中低微摩尔浓度分钟内可逆地形成，从而提供亚微摩尔的平衡常数（ķ当量≈10 5 -10 6 米-1）。用模型蛋白硫氧还蛋白和白蛋白证明了在生理条件下的有效蛋白结合，并通过质谱和凝胶电泳进行了表征。
• Structure-Based Optimization of Small-Molecule Inhibitors for the β-Catenin/B-Cell Lymphoma 9 Protein–Protein Interaction
  作者：Min Zhang、Zhen Wang、Yongqiang Zhang、Wenxing Guo、Haitao Ji

  DOI：10.1021/acs.jmedchem.8b00068

  日期：2018.4.12

  cell-based activities of β-catenin/B-cell lymphoma 9 (BCL9) inhibitors based on the 4′-fluoro-N-phenyl-[1,1′-biphenyl]-3-carboxamide scaffold, which was designed to mimic the side chains of the hydrophobic α-helical hot spots at positions i, i + 3, and i + 7. Compound 29 was found to disrupt the β-catenin/BCL9 protein–protein interaction (PPI) with a Ki of 0.47 μM and >1900-fold selectivity for β-catenin/BCL9

  进行了基于结构的优化，以改善基于4'-氟-N-苯基-[1,1'-联苯基] -3-羧酰胺支架，旨在模拟位置i，i + 3和i + 7的疏水性α螺旋热点的侧链。发现化合物29破坏了β-catenin/ BCL9蛋白–与K i的蛋白质相互作用（PPI）β-catenin/ BCL9的选择性为0.47μM，对β-catenin/ E-cadherin PPI的选择性> 1900倍。拟议的新型抑制剂结合模式与定点诱变和结构-活性关系研究的结果一致。基于细胞的研究表明，有29种干扰β-catenin/ BCL9相互作用而不会影响β-catenin/ E-cadherin相互作用，选择性抑制Wnt /β-catenin信号转激活，下调Wnt目标基因的表达，并抑制Wnt的活力/β-catenin依赖性癌细胞的剂量依赖性。生化和基于细胞的测定结果的比较为将来抑制剂的优化提供了指导。