3-溴-5-甲基苯基硼酸 | 849062-36-8

• 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: 3-溴-5-甲基苯基硼酸
• 中文别名: 3-溴-5-甲基苯硼酸
• 英文名称: (3-bromo-5-methylphenyl)boronic acid
• 英文别名: 3-Bromo-5-methylphenylboronic acid
• CAS: 849062-36-8
• 化学式: C₇H₈BBrO₂
• 分子量: 214.854
• InChiKey: KKEPYOBFWSGWLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  278-283 °C(lit.)
• 沸点：
  351.8±52.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.44
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2931900090
• 安全说明：
  S22,S24/25
• 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
3-Bromo-5-methylphenylboronic acid
Product Name:
Synonyms:

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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.
3-Bromo-5-methylphenylboronic acid
Ingredient name:
CAS number: 849062-36-8

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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: C7H8BBrO2
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, 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：

  3-溴-5-甲基苯基硼酸 在 双氧水 、 potassium carbonate 、 potassium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 3.33h， 生成 1-溴-3-甲氧基-5-甲苯
  参考文献：
  名称：

  一种3-甲基-5-甲氧基苯磺酰氯的制备工艺

  摘要：

  本发明公开了一种3‑甲基5‑甲氧基苯磺酰氯的制备工艺。包含以下步骤：以3,5‑二溴甲苯为起始原料，经硼酸化反应得3‑甲基‑5‑溴苯硼酸，3‑甲基‑5‑溴苯硼酸经氧化反应得3‑甲基‑5‑溴苯酚，3‑甲基‑5‑溴苯酚经取代反应得3‑甲基‑5‑甲氧基溴苯，3‑甲基‑5‑甲氧基溴苯经磺酸化得3‑甲基5‑甲氧基苯磺酸，3‑甲基5‑甲氧基苯磺酸经取代反应得目标化合物3‑甲基‑5‑甲氧基苯磺酰氯。此路线原料易得、后处理简便易行，收率较高，具有较好的应用价值。

  公开号：

  CN107501132A
• 作为产物：
  描述：

  硼酸三异丙酯 、 3,5-二溴甲苯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以90.7%的产率得到3-溴-5-甲基苯基硼酸
  参考文献：
  名称：

  一种3-甲基-5-甲氧基苯磺酰氯的制备工艺

  摘要：

  本发明公开了一种3‑甲基5‑甲氧基苯磺酰氯的制备工艺。包含以下步骤：以3,5‑二溴甲苯为起始原料，经硼酸化反应得3‑甲基‑5‑溴苯硼酸，3‑甲基‑5‑溴苯硼酸经氧化反应得3‑甲基‑5‑溴苯酚，3‑甲基‑5‑溴苯酚经取代反应得3‑甲基‑5‑甲氧基溴苯，3‑甲基‑5‑甲氧基溴苯经磺酸化得3‑甲基5‑甲氧基苯磺酸，3‑甲基5‑甲氧基苯磺酸经取代反应得目标化合物3‑甲基‑5‑甲氧基苯磺酰氯。此路线原料易得、后处理简便易行，收率较高，具有较好的应用价值。

  公开号：

  CN107501132A

文献信息

• [EN] SMALL MOLECULE INHIBITORS OF NF-kB INDUCING KINASE<br/>[FR] INHIBITEURS À PETITE MOLÉCULE DE KINASE INDUISANT NF-KB
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2020239999A1

  公开（公告）日：2020-12-03

  The present invention relates to compounds that inhibit NIK and pharmaceutical compositions comprising such compounds and methods of using the same. These compounds and pharmaceutical compositions are envisaged to be useful for preventing or treating diseases such as cancer (such as B-cell malignancies including leukemias, lymphomas and myeloma), inflammatory disorders, autoimmune disorders, immunodermatologic disorders such as palmoplantar pustulosis and hidradenitis suppurativa, and metabolic disorders such as obesity and diabetes.

  本发明涉及抑制NIK的化合物，以及包含这些化合物的药物组合物和使用方法。这些化合物和药物组合物预期能用于预防或治疗癌症（如包括白血病、淋巴瘤和多发性骨髓瘤的B细胞恶性肿瘤）、炎症性疾病、自身免疫疾病、免疫皮肤病学疾病（如掌跖脓疱病和化脓性汗腺炎）以及代谢紊乱疾病（如肥胖和糖尿病）。
• [EN] TRIAZOLES FOR THE TREATMENT OF DEMYELINATING DISEASES<br/>[FR] TRIAZOLES POUR LE TRAITEMENT DE MALADIES LIÉES À LA DÉMYÉLINISATION
  申请人：VERTEX PHARMA

  公开号：WO2016197009A1

  公开（公告）日：2016-12-08

  The invention relates to triazole compounds of formula I and I' or pharmaceutically acceptable salts thereof, useful as modulators of demyelinating diseases: The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention, methods of using the compositions and kits thereof in the treatment of various demyelinating and neurodegenerative diseases, including multiple sclerosis.

  该发明涉及式I和I'的三唑化合物或其药学上可接受的盐，用作脱髓鞘疾病的调节剂：该发明还提供了包括该发明化合物的药学上可接受的组合物，以及在治疗各种脱髓鞘和神经退行性疾病，包括多发性硬化症中使用这些组合物的方法和工具包。
• A practical and general ipso iodination of arylboronic acids using N-iodomorpholinium iodide (NIMI) as a novel iodinating agent: mild and regioselective synthesis of aryliodides
  作者：R. H. Tale、G. K. Toradmal、V. B. Gopula

  DOI：10.1039/c5ra18820b

  日期：——

  A mild and efficient protocol for the ipso-iodination of aryl boronic acids using N-iodomorpholinium iodide (NIMI) generated in situ from morpholine and molecular iodine as a novel iodinating agent has been developed. The addition of a catalytic amount of copper iodide found to promote rate enhancement of the iodination reaction and dramatic increase in the yield depending upon the nature of the boronic

  为A温和高效的协议本位的芳基硼酸使用-iodination Ñ -iodomorpholinium碘（NIMI）产生原位从吗啉和分子碘作为一种新型的碘化剂已经研制成功。观察到添加催化量的碘化铜可以促进碘化反应的速率提高，并且取决于硼酸的性质，可以显着提高产率。机理研究表明，取决于基材的性质，经典的ipso取代或铜催化的碘脱硼化途径总体上主导了目前的碘化反应。诸如温和的反应条件，操作简便，高至优异的收率，优异的官能团相容性和较低的催化剂载量等特征使该方法潜在地可用于有机合成中。
• Enantioselective Synthesis of Chiral Cyclopent-2-enones by Nickel-Catalyzed Desymmetrization of Malonate Esters
  作者：Somnath Narayan Karad、Heena Panchal、Christopher Clarke、William Lewis、Hon Wai Lam

  DOI：10.1002/anie.201805578

  日期：2018.7.16

  enantioselective synthesis of highly functionalized chiral cyclopent-2-enones by the reaction of alkynyl malonate esters with arylboronic acids is described. These desymmetrizing arylative cyclizations are catalyzed by a chiral phosphinooxazoline/nickel complex, and cyclization is enabled by the reversible E/Z isomerization of alkenylnickel species. The general methodology is also applicable to the synthesis of

  描述了通过丙二酸炔基酯与芳基硼酸的反应的高官能化手性环戊-2-烯酮的对映选择性合成。通过手性膦基恶唑啉/镍络合物催化这些脱对称芳基环化反应，并且通过烯基镍物质的可逆E / Z异构化作用实现环化反应。通用方法也适用于1,6-二氢吡啶3-3（2H）-one的合成。
• <i>Ipso</i> Nitration of Aryl Boronic Acids Using Fuming Nitric Acid
  作者：James I. Murray、Maria V. Silva Elipe、Kyle D. Baucom、Derek B. Brown、Kyle Quasdorf、Seb Caille

  DOI：10.1021/acs.joc.1c00886

  日期：2022.2.18

  The ipso nitration of aryl boronic acid derivatives has been developed using fuming nitric acid as the nitrating agent. This facile procedure provides efficient and chemoselective access to a variety of aromatic nitro compounds. While several activating agents and nitro sources have been reported in the literature for this synthetically useful transformation, this report demonstrates that these processes

  使用发烟硝酸作为硝化剂，已经开发了芳基硼酸衍生物的原位硝化。这种简便的程序提供了对各种芳族硝基化合物的有效和化学选择性访问。虽然文献中已经报道了几种活化剂和硝基源可用于这种综合有用的转化，但本报告表明这些过程可能会产生一种常见的活性试剂无水 HNO 3。动力学和机理研究表明，HNO 3中的反应级数大于2，表明• NO 2自由基是活性物质。