4-氟-2-醛基苯硼酸 | 825644-26-6

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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-氟-2-醛基苯硼酸
• 中文别名: 4-氟-2-甲酰基苯硼酸
• 英文名称: (4-fluoro-2-formylphenyl)boronic acid
• CAS: 825644-26-6
• 化学式: C₇H₆BFO₃
• mdl: MFCD10697426
• 分子量: 167.932
• InChiKey: QWUBOCQWTPCPNE-UHFFFAOYSA-N

物化性质

• 熔点：
  123-125 °C
• 沸点：
  341.9±52.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于乙腈（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  12
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2～8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Fluoro-2-formylphenylboronic 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: 4-Fluoro-2-formylphenylboronic acid
CAS number: 825644-26-6

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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, refrigerated.
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: C7H6BFO3
Molecular weight: 167.9

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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

制备方法与用途

4-氟-2-醛基苯硼酸可以作为有机合成中间体和医药中间体，主要用于实验室研发和医药化工的合成过程。

反应信息

• 作为反应物：
  描述：

  4-氟-2-醛基苯硼酸 在 aluminum oxide 、 C₂₂H₂₂Cl₃N₃O₄ 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 79.0h， 生成 (S)-2-(5-fluoro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acrylic acid
  参考文献：
  名称：

  3-(α-丙烯酸)苯并氧杂硼杂环化合物的设计和对映选择性合成以对抗碳青霉烯酶耐药性

  摘要：

  手性 3-取代苯并氧硼杂环被设计为碳青霉烯酶抑制剂，并通过不对称 Morita-Baylis-Hillman 反应有效合成。一些苯并氧杂硼杂环戊烯是临床相关碳青霉烯酶的有效抑制剂，并恢复含有这些酶的细菌中美罗培南的活性。晶体学分析验证了所提出的与碳青霉烯酶结合的机制，即以与其抗生素底物相关的方式。结果说明了基于结构的设计方法与不对称催化相结合如何有效地产生有效的β-内酰胺酶抑制剂，并为开发对抗碳青霉烯酶的药物提供了起点。

  DOI：

  10.1039/d1cc03026d
• 作为产物：
  描述：

  2-(2-bromo-5-fluorophenyl)-1,3-dioxolane 在 正丁基锂 、 硼酸三异丙酯 、 盐酸 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以77%的产率得到4-氟-2-醛基苯硼酸
  参考文献：
  名称：

  [EN] DUAL NK1/NK3 ANTAGONISTS FOR TREATING SCHIZOPHRENIA
  [FR] ANTAGONISTES DOUBLES DES RECEPTEURS NK1/NK3 POUR TRAITER LA SCHIZOPHRENIE

  摘要：

  使用一般式化合物，其中取代基如权利要求1中所述，或其药用活性酸盐，用于制备治疗精神分裂症的药物。

  公开号：

  WO2005002577A1

文献信息

• [EN] 1-HYDROXY-1,3-DIHYDROBENZO[c][1,2]OXABOROLES AND THEIR USE AS HERBICIDES<br/>[FR] 1-HYDROXY-1,3-DIHYDROBENZO[C][1,2]OXABOROLES ET UTILISATION DE CES DERNIERS EN TANT QU'HERBICIDES
  申请人：DOW AGROSCIENCES LLC

  公开号：WO2018156554A1

  公开（公告）日：2018-08-30

  Provided herein are 1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaboroles and their derivatives, and compositions and methods of use thereof as herbicides.

  本文提供了1-羟基-1,3-二氢苯并[c][1,2]氧硼烷及其衍生物，以及它们作为除草剂的组合物和使用方法。
• Pd(II)-Catalyzed Asymmetric Annulation toward the Synthesis of 2,3-Disubstituted Chiral Indenols
  作者：Chang-Xue Gu、Wen-Wen Chen、Ming-Hua Xu

  DOI：10.1021/acs.joc.9b02958

  日期：2020.3.6

  An enantioselective asymmetric annulation of 2-formylboronic acids with internal alkynes has been realized using a chiral phosphinooxazoline/palladium(II) catalyst. The reaction tolerates a variety of alkynes including the relatively inert diaryl substituted internal ones. A wide range of optically active 2,3-disubstituted indenols was afforded in high yields with good to excellent enantioselectivities

  使用手性膦基恶唑啉/钯（II）催化剂已经实现了2-甲酰基硼酸与内部炔的对映选择性不对称环化。该反应可耐受多种炔烃，包括相对惰性的二芳基取代的内部炔烃。以高收率和良好至优异的对映选择性（高达99％收率和99％ee）提供了多种旋光性2,3-二取代的茚基。
• [EN] BORON CONTAINING COMPOUNDS AND THEIR USES<br/>[FR] COMPOSÉS CONTENANT DU BORE ET LEURS UTILISATIONS
  申请人：BORAGEN INC

  公开号：WO2020264581A1

  公开（公告）日：2020-12-30

  The present disclosure contemplates a boron-containing compound, a composition containing a pesticidal effective amount of that compound dissolved or dispersed in a carrier medium, and a method of reducing, ameliorating, or controlling an infestation by a pest, particularly a fungus, by administering a contemplated composition to a plant or animal in need.

  本公开涉及一种含硼化合物，其中包含该化合物的杀虫有效量溶解或分散在载体介质中的组合物，以及通过向需要的植物或动物施用所述组合物来减少、改善或控制害虫，特别是真菌侵害的方法。
• [EN] HETEROAROMATIC MACROCYCLIC ETHER CHEMOTHERAPEUTIC AGENTS<br/>[FR] AGENTS CHIMIOTHÉRAPEUTIQUES À BASE D'ÉTHER MACROCYCLIQUE HÉTÉROAROMATIQUE
  申请人：NUVALENT INC

  公开号：WO2021226269A1

  公开（公告）日：2021-11-11

  Disclosed are heterocyclic heteroaromatic macrocyclic ether compounds, pharmaceutically acceptable salts of the compounds and pharmaceutical compositions thereof. Also disclosed are methods of treating or preventing cancer using the heterocyclic heteroaromatic macrocyclic ether compounds, pharmaceutically acceptable salts of the compounds, and pharmaceutical compositions thereof.

  揭示了杂环杂芳大环醚化合物，这些化合物的药用盐以及它们的药物组合物。还揭示了使用这些杂环杂芳大环醚化合物、这些化合物的药用盐以及它们的药物组合物来治疗或预防癌症的方法。
• 合成萘环衍生物和苯并杂环类化合物的方法
  申请人：陕西师范大学

  公开号：CN104478723B

  公开（公告）日：2016-08-24

  本发明公开了一种合成萘环衍生物和苯并杂环类化合物的方法，该方法是将邻位具有α,β‑不饱和酯的芳基醛和酮类化合物在叔胺、叔膦类有机小分子催化剂的催化下发生类似Mortia‑Baylis‑Hillman的反应，进而失去一分子水生成萘环衍生物或苯并杂环类化合物。本发明操作步骤简单，所用催化剂廉价易得，对环境无害，以较好的收率合成了一系列萘环衍生物和苯并杂环类化合物。