2-溴-5-氟苯硼酸 | 959996-48-6

• 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: 2-溴-5-氟苯硼酸
• 英文名称: 2-bromo-5-fluorophenylboronic acid
• 英文别名: 2-bromo-5-fluorobenzeneboronic acid；(2-bromo-5-fluorophenyl)boronic acid
• CAS: 959996-48-6
• 化学式: C₆H₅BBrFO₂
• 分子量: 218.818
• InChiKey: NBWMJVDWOGDXIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  326.9±52.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26
• 危险类别码：
  R36
• 海关编码：
  2931900090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H302,H319
• 储存条件：
  存储条件为2-8°C，并需保存在惰性气体中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Bromo-5-fluorophenylboronic 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: 2-Bromo-5-fluorophenylboronic acid
CAS number: 959996-48-6

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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: C6H5BBrFO2
Molecular weight: 218.8

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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, hydrogen bromide.

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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：

  2-溴-5-氟苯硼酸 在 三氟化硼乙醚 、 potassium tert-butylate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.34h， 生成 1-(2-bromo-5-fluorophenoxy)-1H-benzo[d][1,2,3]triazole
  参考文献：
  名称：

  对映体特异性 sp2 -sp3 邻位酚和对位酚与仲硼酸酯和叔硼酸酯的偶联。

  摘要：

  邻位酚和对位酚与仲硼酸酯和叔硼酸酯的偶联已被探索。对于对位取代酚，二锂硫代酚盐与硼酸酯反应后，用Ph3 BiF2 或马丁硫烷处理，得到具有完全对映专一性的偶联产物。该方法应用于广谱抗菌天然产物(-)-4-(1,5-二甲基己-4-烯基)-2-甲基苯酚的合成。对于邻位取代的苯酚，需要首先在苯酚氧原子上掺入苯并三唑。随后的邻位锂化和硼化得到偶联产物，同样具有完全的立体特异性。

  DOI：

  10.1002/anie.201710777
• 作为产物：
  描述：

  2-碘-4-氟溴苯 在 异丙基氯化镁 、 硼酸三异丙酯 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-溴-5-氟苯硼酸
  参考文献：
  名称：

  Fused, Tricyclic Sulfonamide Inhibitors of Gamma Secretase

  摘要：

  该发明提供了公式I的化合物： 或其药用盐，其中R 1 ，R 2 和A、B和C环如本文所定义。公式I的化合物在治疗或预防认知障碍，如阿尔茨海默病方面是有用的。该发明还涵盖了包括公式I的化合物或盐的药物组合物，制备所需化合物的方法，以及使用公式I的化合物或盐治疗认知障碍，如阿尔茨海默病的方法。

  公开号：

  US20080021056A1

文献信息

• 一种由铜化合物诱导制备菲啶酮类化合物的 方法
  申请人：广州大学

  公开号：CN109320497B

  公开（公告）日：2020-07-31

  本发明属于有机合成、金属催化领域，公开了一种由铜化合物诱导制备菲啶酮类化合物的方法。该方法包括以下步骤：将苯甲酰胺衍生物、邻溴苯硼酸类化合物、铜盐、碱和溶剂在惰性气体保护下加入反应器中，然后加热反应，反应结束后将所得反应液纯化即得所需的菲啶酮类化合物。该方法在氮气和密闭环境中，在碱的存在下，苯甲酰胺衍生物在铜化合物的催化作用下与邻溴苯硼酸发生C‑H活化串联反应生成菲啶酮；该方法所使用的原料、铜盐等简单易得，并且反应操作简单，产率高，有利于工业化生产。
• Enantioselective Dearomative [3 + 2] Umpolung Annulation of <i>N</i>-Heteroarenes with Alkynes
  作者：Peng Yang、Qiang Wang、Bing-Hui Cui、Xiao-Dong Zhang、Hang Liu、Yue-Yuan Zhang、Jia-Liang Liu、Wen-Yu Huang、Ren-Xiao Liang、Yi-Xia Jia

  DOI：10.1021/jacs.1c11092

  日期：2022.1.26

  Enantioselective [3 + 2] annulation of N-heteroarenes with alkynes has been developed via a cobalt-catalyzed dearomative umpolung strategy in the presence of chiral ligand and reducing reagent. A variety of electron-deficient N-heteroarenes, including quinolines, isoquinolines, quinoxaline, and pyridines, and internal or terminal alkynes are employed in this reaction, showing a broad substrate scope

  在手性配体和还原剂存在下，通过钴催化的脱芳环化策略开发了N-杂芳烃与炔烃的对映选择性[3 + 2] 环化。该反应使用了多种缺电子的N-杂芳烃，包括喹啉、异喹啉、喹喔啉和吡啶，以及内部或末端炔烃，显示出广泛的底物范围和良好的官能度耐受性。还开发了用炔烃环化富电子吲哚。该协议提供了对具有出色对映选择性的各种N-螺杂环分子的直接访问（76 个示例，高达 99% ee）。
• Synthesis of fused 1,2-naphthoquinones with cytotoxic activity using a one-pot three-step reaction
  作者：Anton A. Nechaev、Pratap R. Jagtap、Ema Bažíková、Johana Neumannová、Ivana Císařová、Eliška Matoušová

  DOI：10.1039/d1ob00205h

  日期：——

  A method for the synthesis of fused 1,2-naphthoquinones, as analogues of biologically active natural terpene quinones, is described. The intermediate polycyclic naphthalenes were prepared by a one-pot palladium-catalysed process from simple alkynes, one of which was made from an optically pure biomass-derived levoglucosenone. The prepared methoxy-substituted naphthalenes were subsequently transformed

  描述了一种合成稠合 1,2-萘醌的方法，作为具有生物活性的天然萜醌的类似物。中间体多环萘是通过一锅钯催化工艺从简单的炔烃制备的，其中一种是由光学纯的生物质衍生的左旋葡糖烯酮制成的。制备的甲氧基取代的萘随后通过三价碘介导的氧化一步转化为 1,2-萘醌。发现萘醌产品具有细胞毒性。
• [EN] TRICYCLIC HETEROCYCLES USEFUL AS TEAD BINDERS<br/>[FR] HÉTÉROCYCLES TRICYCLIQUES UTILES EN TANT QUE LIANTS TEAD
  申请人：MERCK PATENT GMBH

  公开号：WO2021224291A1

  公开（公告）日：2021-11-11

  The present invention relates to tricyclic heterocycles. These heterocyclic compounds are useful as TEAD binders and/or inhibitors of YAP-TEAD and TAZ-TEAD protein-protein interaction or binding and for the prevention and/or treatment of several medical conditions including hyperproliferative disorders and diseases, in particular cancer.

  本发明涉及三环杂环化合物。这些杂环化合物可用作TEAD结合物，和/或YAP-TEAD和TAZ-TEAD蛋白质间的相互作用或结合的抑制剂，用于预防和/或治疗包括过度增殖性疾病和疾病在内的多种医疗条件，特别是癌症。
• Palladium-Catalyzed Double <i>N</i>-Arylation to Access Unsymmetric <i>N</i>,<i>N</i>′-Bicarbazole Scaffolds
  作者：Huan Zhang、Yi Ding、Mei-Ru Zhang、Chuan-Jun Lu、Jia Feng、Ren-Rong Liu

  DOI：10.1021/acs.joc.3c00637

  日期：2023.7.21

  Herein, the palladium-catalyzed double C–N coupling of 9H-carbazol-9-amines and 2,2′-dibromo-1,1′-biphenyl is reported. This protocol offers access to N,N′-bicarbazole scaffolds, which have frequently been used as linkers in the construction of functional covalent organic frameworks (COFs). A variety of substituted N,N′-bicarbazoles were synthesized in moderate to high yields based on this chemistry

  在此，报道了 9 H-咔唑-9-胺和 2,2'-二溴-1,1'-联苯的钯催化双 C-N 偶联。该协议提供了对N , N'-联咔唑支架的访问，这些支架经常被用作构建功能性共价有机框架 (COF) 的连接体。基于该化学反应，以中等到高产率合成了多种取代的N , N'-联咔唑，并且通过四溴化物4和四炔化物5等COF单体的合成展示了该方法的潜在应用。