2-溴-5-甲氧基苯基硼酸 | 89694-44-0

• 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 - 苯酚醚
• 中文名称: 2-溴-5-甲氧基苯基硼酸
• 中文别名: 2-溴-5-甲氧基苯硼酸
• 英文名称: 2-bromo-5-methoxyphenylboronic acid
• 英文别名: 2-bromo-5-methoxybenzene boronic acid；(2-bromo-5-methoxyphenyl)boronic acid
• CAS: 89694-44-0
• 化学式: C₇H₈BBrO₃
• 分子量: 230.854
• InChiKey: BJQKEDXKQVNQPR-UHFFFAOYSA-N

物化性质

• 熔点：
  214-216
• 沸点：
  376.6±52.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.14
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 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
• 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
2-Bromo-5-methoxyphenylboronic 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.
2-Bromo-5-methoxyphenylboronic acid
Ingredient name:
CAS number: 89694-44-0

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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, refrigerated.

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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: C7H8BBrO3
Molecular weight: 230.9

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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

制备方法与用途

概述

2-溴-5-甲氧基苯基硼酸可用作医药合成中间体和有机中间体。它适用于实验室研发过程和化工医药研发过程中，可通过3-甲氧基苯基硼酸、三苯膦硫化物以及N-溴琥珀酰亚胺制备。

制备

在氩气气氛下，将300毫升茄形烧瓶中加入3-甲氧基苯基硼酸（9.12克，60.0毫摩尔）、三苯膦硫化物（932毫克，6.00毫摩尔）和二氯甲烷（200毫升），搅拌以形成均匀溶液。随后向其中加入N-溴琥珀酰亚胺（13.0克，72.0毫摩尔）。将混合物在室温下搅拌2天。

向反应混合物中加入饱和硫代硫酸钠水溶液终止反应，然后用二氯甲烷（100毫升×3）萃取。合并的有机层使用饱和盐水洗涤，并经硫酸钠干燥。过滤后，减压浓缩以获得粗产物。最后，通过硅胶柱色谱法（290克，正己烷/丙酮＝1/1）纯化得到2-溴-5-甲氧基苯基硼酸（8.45克，36.6毫摩尔），产率为61.0%。

反应信息

• 作为反应物：
  描述：

  2-溴-5-甲氧基苯基硼酸 在 正丁基锂 、 三氟化硼乙醚 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 19.84h， 生成
  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：

  m-Methoxy-benzolboronsaeureanhydrid 在 溴 、 溶剂黄146 、 sodium bromide 作用下， 生成 2-溴-5-甲氧基苯基硼酸
  参考文献：
  名称：

  Electrophilic Displacement Reactions. XIV. Two Novel Reactions Involving Areneboronic Acids and Halogens^1-3

  摘要：

  DOI：

  10.1021/jo01050a032

文献信息

• [EN] ATROPISOMERISM FOR ENHANCED KINASE INHIBITOR SELECTIVITY<br/>[FR] ATROPISOMÉRISME POUR UNE SÉLECTIVITÉ AMÉLIORÉE DES INHIBITEURS DE KINASE
  申请人：SAN DIEGO STATE UNIV RESEARCH FOUNDATION

  公开号：WO2018237134A1

  公开（公告）日：2018-12-27

  The invention provides a series of conformationally stable and selective kinase inhibitors, and methods of using the kinase inhibitors. The effect of atropisomerism on kinase selectivity was assessed, finding improved selectivity compared to rapidly interconverting parent compounds. The compounds herein are atropisomers having increased kinase selectivity, and are for use in treating conditions that benefit from selective kinase inhibition.

  这项发明提供了一系列构象稳定且选择性激酶抑制剂，以及使用这些激酶抑制剂的方法。评估了扭曲异构体对激酶选择性的影响，发现与快速相互转化的母体化合物相比，选择性得到了改善。本文中的化合物是具有增强激酶选择性的扭曲异构体，用于治疗受益于选择性激酶抑制的疾病。
• Mild Silver(I)-Mediated Regioselective Iodination and Bromination of Arylboronic Acids
  作者：Raed M. Al-Zoubi、Dennis G. Hall

  DOI：10.1021/ol100537x

  日期：2010.6.4

  A convenient and regioselective silver(I)-mediated electrophilic iodination and bromination reaction of arylboronic acids has been developed. The boronic acid does not require protection prior to the reaction, which can be performed on a multigram scale with moderate to excellent yields. A mild, simple, and effective method is disclosed to provide ortho-haloarylboronic acids that can be used as useful

  已经开发了方便且区域选择性的银（I）介导的芳基硼酸的亲电子碘化和溴化反应。硼酸在反应之前不需要保护，该保护可以在数克规模上以中等至极好的收率进行。公开了一种温和，简单且有效的方法，以提供邻-卤代芳基硼酸，其可用作选择性顺序Suzuki-Miyaura交叉偶联反应中的有用中间体，从而以高收率提供邻-三芳基衍生物。
• One Substrate, Two Modes of C–H Functionalization: A Metal-Controlled Site-Selectivity Switch in C–H Arylation Reactions
  作者：Virendra Kumar Tiwari、Neha Kamal、Manmohan Kapur

  DOI：10.1021/acs.orglett.6b03558

  日期：2017.1.6

  site-selectivity switch has been achieved in the ruthenium-catalyzed C–H arylation reaction of N-acetyl-1,2-dihydroisoquinolines. This metal-mediated switch is antipodal to the previous report on the palladium-mediated C-4 C–H arylation on the same substrate. Mechanistic details reveal interesting aspects of the reaction pathway, and kinetic studies bring out the difference in the modes of C–H activation

  在钌催化的N-乙酰基1,2,2-二氢异喹啉的C–H芳基化反应中，已经实现了独特的位点选择性转换。这种金属介导的开关与先前报道的在同一基质上钯介导的C-4 C–H芳基化反应相反。机理细节揭示了反应途径的有趣方面，动力学研究揭示了两种催化体系采用的C–H活化方式的差异。
• Synthesis of Sugar-Based Enones and Their Transformation into 3,5-Disubstituted Furans and 2-Acyl-Substituted 1,2,3-Trideoxy Sugars in the Presence of Lewis Acids
  作者：Nazar Hussain、Monika Bhardwaj、Ajaz Ahmed、Debaraj Mukherjee

  DOI：10.1021/acs.orglett.9b00680

  日期：2019.5.3

  carbonylative cross-coupling reactions of 2-iodoglycals have been developed for the synthesis of sugar-based arylones and ynones using formic acid as the carbonyl source. Whereas acetyl-protected arylones lead to the formation of highly substituted furan derivatives in the presence of Lewis acid, benzyl-protected arylones furnished the 3-deoxy sugar derivative. In the presence of nucleophiles, an attack

  已经开发了Pd催化的2-碘代糖的羰基交叉偶联反应，用于使用甲酸作为羰基源来合成糖基丙二酮和炔酮。尽管在路易斯酸的存在下，乙酰基保护的芳基酮导致形成高度取代的呋喃衍生物，而苄基保护的芳基酮提供了3-脱氧糖衍生物。在存在亲核试剂的情况下，取决于亲核试剂的性质，对C-1或C-3碳进行区域和立体选择性的攻击。
• Benzotriazine inhibitors of kinases
  申请人：Noronha Glenn

  公开号：US20050245524A1

  公开（公告）日：2005-11-03

  The invention provides benzotriazine compounds having formula (I). The benzotriazine compounds of the invention are capable of inhibiting kinases, such members of the Src kinase family, and various other specific receptor and non-receptor kinases.

  该发明提供了具有化学式（I）的苯并三唑化合物。该发明的苯并三唑化合物能够抑制激酶，如Src激酶家族成员，以及其他特定的受体和非受体激酶。