2-溴-5-三氟甲基苯硼酸 | 957034-38-7

• 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: 2-溴-5-三氟甲基苯硼酸
• 中文别名: (2-溴-5-(三氟甲基)苯基)硼酸
• 英文名称: (2-bromo-5-(trifluoromethyl)phenyl)boronic acid
• 英文别名: [2-bromo-5-(trifluoromethyl)phenyl]boronic acid
• CAS: 957034-38-7
• 化学式: C₇H₅BBrF₃O₂
• 分子量: 268.826
• InChiKey: MMCSHRKBEOIKBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  5

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

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Bromo-5-trifluoromethylphenylboronic acid
Synonyms: 2-Bromo-5-(trifluoromethyl)phenylboronic acid

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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-trifluoromethylphenylboronic acid
CAS number: 957034-38-7

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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: C7H5BBrF3O2
Molecular weight: 268.8

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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-5-三氟甲基苯硼酸 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.0h， 生成 11-(trifluoromethyl)-3,4-dihydrodibenzo[f,h]quinolin-2(1H)-one
  参考文献：
  名称：

  Trans-4a,12b/3,4-Dihydrodibenzo[f,h]quinolin-2(1H)-Ones 和 Dibenzo[f,h]quinolin-2(1H)-Ones 通过 6-Biphenylpyridine-2( 1H)-个

  摘要：

  的合成反式-4一个，12 b二氢二苯[ ˚F，ħ ]喹啉-2（1 H ^） -酮（2） ，二苯并[ ˚F，ħ ]喹啉-2（1 H ^） -酮（3）和3 ,4-dihydrodibenzo[ f , h ]quinolin-2(1 H )-ones ( 4) 通过光致环化 6-([1,1'-biphenyl]-2-yl)pyridine-2(1 H ) -ones ( 1)在 313 nm 紫外光照射下进行了描述。化合物2当辐照时间为 3 小时时，产率为 82-95%。通过在碘存在下照射1 12 小时获得产物3。将2在 DMF 中的溶液在 130 °C 下加热24 小时，通过双 1,3-H 位移得到化合物4。演示的协议显示了化合物1的光诱导环化的多样性。

  DOI：

  10.1002/adsc.202100509
• 作为产物：
  描述：

  对溴三氟甲苯 在 盐酸 、 异丙基溴化镁 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 2.83h， 生成 2-溴-5-三氟甲基苯硼酸
  参考文献：
  名称：

  通过TMS组的钯催化的CH活化获得甲硅烷基吡唑衍生物

  摘要：

  提出了一种简单有效的方法，用于在药物化学中具有潜在用途的新型甲硅烷基杂环。一组溴苯基三甲基甲硅烷基吡唑中间体可通过直接的有机金属途径转化为两类区域异构的碘代芳基底物。使用芳基锌或芳基锂化学方法，TMS基团保留在吡唑环上或易位至芳基部分。依靠单步环化作用，这两个家族可以有效地转化为苯甲硅基吡唑，这要归功于Pd催化的未活化C（sp 3）-H键α到硅原子的活化。与吡唑环完全相容的实验条件表明，该反应是通过协同的金属化-去质子化（CMD）机制发展的。

  DOI：

  10.1002/chem.201601533

文献信息

• Oxidant-Free Au(I)-Catalyzed Halide Exchange and C_sp2–O Bond Forming Reactions
  作者：Jordi Serra、Christopher J. Whiteoak、Ferran Acuña-Parés、Marc Font、Josep M. Luis、Julio Lloret-Fillol、Xavi Ribas

  DOI：10.1021/jacs.5b08756

  日期：2015.10.21

  character, Au(I)/Au(III) redox properties or a combination of both. As a result of the high oxidation potential of the Au(I)/Au(III) couple, redox catalysis involving Au typically requires the use of a strong external oxidant. This study demonstrates unusual external oxidant-free Au(I)-catalyzed halide exchange (including fluorination) and Csp2-O bond formation reactions utilizing a model aryl halide macrocyclic

  Au 已被证明通过利用其 π 路易斯酸特性、Au(I)/Au(III) 氧化还原特性或两者的组合来介导许多有机转化。由于 Au(I)/Au(III) 对的高氧化电位，涉及 Au 的氧化还原催化通常需要使用强外部氧化剂。该研究展示了不寻常的无外部氧化剂 Au(I) 催化的卤化物交换（包括氟化）和使用模型芳基卤化物大环底物的 Csp2-O 键形成反应。此外，卤化物交换和 Csp2-O 偶联反应性也可以外推到带有单个螯合基团的底物，从而进一步了解反应机制。这项工作提供了无外部氧化剂的 Au(I) 催化碳-杂原子交叉偶联反应的第一个例子。
• Cyclic Diaryl λ ³ ‐Bromanes as Original Aryne Precursors
  作者：Matteo Lanzi、Quentin Dherbassy、Joanna Wencel‐Delord

  DOI：10.1002/anie.202103625

  日期：2021.6.25

  cyclic diaryl λ3-bromanes. These unique compounds feature reactivity that is appealing and complementary to that of λ3-iodanes, generating arynes under mild reaction conditions and in the presence of a weak base. Accordingly, formal meta-selective transition-metal-free C–O and C–N couplings may be achieved. Mechanistic studies unambiguously support the aryne generation mechanism.

  尽管高价碘得到广泛应用，但相应的 λ 3 -溴烷却鲜有研究。在此，我们报告了一种获得环状二芳基 λ 3 -溴烷的通用、安全且高产的策略。这些独特的化合物具有与 λ 3 -碘烷互补的反应性，可在温和的反应条件和弱碱存在下生成芳炔。因此，正规的元-选择性过渡金属-自由C-O和C-N偶联可以实现。机理研究明确支持芳炔生成机制。
• One-Pot Three-Component Synthesis of Phenanthrenes via Palladium-Catalyzed Catellani and <i>Retro</i>-Diels–Alder Reactions
  作者：Tianxin Hao、Wei Gao、Sitian Yuan、Yi Liu、Yiqing Li、Yang Fu、Qiuping Ding

  DOI：10.1021/acs.joc.2c02880

  日期：2023.8.4

  efficient one-pot three-component palladium-catalyzed domino reaction of aryl iodide, 2-bromophenylboronic acid, and norbornadiene to produce phenanthrenes has been developed. Norbornadiene serves both as the activator of ortho-C–H bond and the source of ethylene via a retro-Diels–Alder reaction. The method features inexpensive and readily available substrates, a broad range of functional groups, and

  开发了一种高效的一锅三组分钯催化的芳基碘、2-溴苯基硼酸和降冰片二烯多米诺反应来生产菲。降冰片二烯既可作为邻位-C–H 键的活化剂，又可作为逆狄尔斯 - 阿尔德反应的乙烯来源。该方法具有廉价且容易获得的底物、广泛的官能团和良好的产率的特点。
• Synthesis of Oxadihydrophenanthroquinolizidinones by Photoinduced Rearrangement of 3‐Biphenyl‐1‐hydroxypropyl‐pyridin‐2(1H)‐ones
  作者：Jingzhi Sui、Ding Wang、Tao Wang、Kexin Ren、Zunting Zhang

  DOI：10.1002/adsc.202400041

  日期：2024.7.16

  synthesis of hexahydro‐11H,15H‐dibenzo[f,h] [1,3]oxazino[3,2‐b]isoquinolin‐15‐ones was achieved via photoinduced rearrangement of 3‐biphenyl‐1‐hydroxypropyl‐pyridin‐2(1H)‐ones with a 313 nm UV light. Trans‐(8b,15a)‐9a‐β‐hexahydro‐11H,15H‐dibenzo[f,h][1,3]oxazino[3,2‐b]isoquinolin‐15‐ones and trans‐(8b,15a)‐9a‐α‐hexahydro‐11H,15H‐dibenzo[f,h][1,3] oxazino[3,2‐b]isoquinolin‐15‐ones were obtained in 76‐92%

  通过3-联苯-1-羟丙基-吡啶-2的光诱导重排合成六氢-11H,15H-二苯并[f,h][1,3]恶嗪基[3,2-b]异喹啉-15-酮(1H)-具有 313 nm 紫外光的分子。 反式-(8b,15a)-9a-β-六氢-11H,15H-二苯并[f,h][1,3]恶嗪基[3,2-b ]异喹啉-15-酮和反式-(8b,15a)-9a-α-六氢-11H,15H-二苯并[f,h][1,3]恶嗪基[3,2-b]异喹啉-15-酮通过一锅反应获得 76-92% 的产率。或者，在 HCl 水溶液 (1 M) 存在下照射 3-联苯-1-羟丙基-吡啶-2(1H)-酮，导致形成顺式-(8b,15a)-9a-β-六氢- 11H,15H-二苯并[f,h][1,3]恶嗪基[3,2-b]异喹啉-15-酮和顺-(8b,15a) ‐ 9a-α-六氢-11H,15H-二苯并[f,h][1,3]恶嗪基[3,2-b]异喹啉-15