4-溴-2-甲基苯硼酸 | 221006-71-9

• 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-溴-2-甲基苯硼酸
• 中文别名: 4-溴-2-甲基苯基硼酸
• 英文名称: 4-bromo-2-methylphenylboronic acid
• 英文别名: (4-bromo-2-methylphenyl)boronic acid
• CAS: 221006-71-9
• 化学式: C₇H₈BBrO₂
• 分子量: 214.854
• InChiKey: BEQUDVVISBTSHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  331.0±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

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-2-methylphenylboronic 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-Bromo-2-methylphenylboronic acid
CAS number: 221006-71-9

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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.
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: 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：

  4-溴-2-甲基苯硼酸 在 四(三苯基膦)钯 、 二(三叔丁基膦)钯 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl 3-(4-(5-(3-cyano-4-isopropyloxyphenyl)-1,3-thiazol-2-yl)-3-methylphenyl)propanoate
  参考文献：
  名称：

  鞘氨醇-1-磷酸1（S1P1）受体的高度选择性和强效激动剂。

  摘要：

  通过系统的SAR开发了一系列新的鞘氨醇-1-磷酸（S1P）受体激动剂，旨在实现对S1P受体家族的单个成员S1P1的高选择性。优化的结构代表了高度S1P1选择性和有效的激动剂：S1P1 / S1P2，S1P1 / S1P3，S1P1 / S1P4> 10,000倍，S1P1 / S1P5> 600倍，而EC50（S1P1）<0.2 nM。体内实验与单独的S1P1受体激动作用是一致的，足以实现所需的降低淋巴细胞的作用。

  DOI：

  10.1016/j.bmcl.2006.04.064
• 作为产物：
  描述：

  2,5-二溴甲苯 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 7.0h， 生成 4-溴-2-甲基苯硼酸
  参考文献：
  名称：

  Side functionalization of diboronic acid precursors for covalent organic frameworks

  摘要：

  一系列取代的1,4-苯二硼酸（BDBA）被合成，并研究了它们的热性质。选择两种二硼酸作为共价有机骨架（COF）形成的构建块，即2,5-二甲氧基-1,4-苯二硼酸和2-硝基-1,4-苯硼酸。有趣的是，BDBA核心的取代导致了聚合温度的显著降低，从而形成了较为无序的结构。

  DOI：

  10.1039/c3ce26494g

文献信息

• Selective Synthesis of <i>ortho-</i>Substituted Diarylsulfones by Using NHC-Au Catalysts under Mild Conditions
  作者：Haibo Zhu、Yajing Shen、Daheng Wen、Zhang-Gao Le、Tao Tu

  DOI：10.1021/acs.orglett.8b03957

  日期：2019.2.15

  A single-step gold(I)-catalyzed chemoselective protocol to access ortho-substituted diarylsulfones has been established. Acenaphthoimidazolylidene gold complexes are effective catalysts for the arylsulfonylation of boronic acids by potassium metabisulfite (K2S2O5) and diaryliodonium salts to access (poly-)ortho-substituted diarylsulfones even in gram scale. Unlike the transition metal-catalyzed two-component

  已经建立了一步金（I）催化的化学选择方案以访问邻位取代的二芳基砜。ena啶咪唑基亚金络合物是焦亚硫酸氢钾（K 2 S 2 O 5）和二芳基碘鎓盐对硼酸进行芳基磺酰化的有效催化剂，即使以克为单位，也可得到（多）邻位取代的二芳基砜。与过渡金属催化的双组分偶联系统不同，二芳基碘鎓盐中的位阻芳基优先转移到体积较小的芳基上，以形成合成困难的靶标，包括具有药学重要性的靶标。
• [EN] DIHYDROPYRAZOLE GPR40 MODULATORS<br/>[FR] MODULATEURS DIHYDROPYRAZOLES DE GPR40
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2014078608A1

  公开（公告）日：2014-05-22

  The present invention provides compounds of Formula (I): or a stereoisomer, or a pharmaceutically acceptable salt thereof, wherein all of the variables are as defined herein. These compounds are GPR40 G protein-coupled receptor modulators which may be used as medicaments.

  本发明提供了化合物的公式(I)：或其立体异构体，或其药学上可接受的盐，其中所有变量均如本文所定义。这些化合物是GPR40 G蛋白偶联受体调节剂，可用作药物。
• 2,6,7,8 SUBSTITUTED PURINES AS HDM2 INHIBITORS
  申请人：MERCK SHARP & DOHME CORP.

  公开号：US20150353553A1

  公开（公告）日：2015-12-10

  The present invention provides 2,6,7,8 Substituted Purines as described herein or a pharmaceutically acceptable salt thereof. The representative compounds are useful as inhibitors of the HDM2 protein. Also disclosed are pharmaceutical compositions comprising the above compounds and potential methods of treating cancer using the same.

  本发明提供了如本文所述的2,6,7,8取代嘌呤或其药学上可接受的盐。这些代表性化合物可用作HDM2蛋白的抑制剂。本发明还公开了包含上述化合物的药物组合物以及使用它们治疗癌症的潜在方法。
• 10.1021/acs.orglett.4c01043
  作者：Jiang, Hui、Torigoe, Takeru、Kuninobu, Yoichiro

  DOI：10.1021/acs.orglett.4c01043

  日期：——

  involves the introduction of boronyl groups. However, an alternative route that involves the functionalization of boronic acids has not received much attention. This study describes the catalytic C(sp3)–H alkylation of ortho-tolylboronic acids utilizing the interaction between a free boronyl group [−B(OH)2] and a decatungstate photocatalyst [W10O32]4–. The boronyl groups of the alkylated products could be

  硼酸合成主要涉及硼基的引入。然而，涉及硼酸官能化的替代途径尚未受到太多关注。本研究描述了利用游离硼基 [−B(OH) 2 ] 和十钨酸盐光催化剂 [W 10 O 32 ] 4–之间的相互作用对邻甲苯基硼酸进行催化 C(sp 3 )–H 烷基化。烷基化产物的硼基基团可以在不分离烷基化产物的情况下被转化。
• 10.1016/j.ejmech.2024.116473
  作者：Li, Huiqiong、Ke, Ran、Zhou, Yang、Chang, Shaohua、Wang, Jie、Su, Chen、Wu, Pinglian、Yang, Bowen、Wang, Zhen、Ding, Ke、Ma, Dawei

  DOI：10.1016/j.ejmech.2024.116473

  日期：——

  Fibroblast growth factor receptor 2 (FGFR2) represents an appealing therapeutic target for multiple cancers, yet no selective FGFR2 inhibitors have been approved for clinical use to date. Here, we report the discovery of a series of new selective, irreversible FGFR2 inhibitors. The representative compound potently inhibited FGFR2 kinase activity with an IC of 5.2 nM, and was >61-, >34-, and >293-fold

  成纤维细胞生长因子受体 2 (FGFR2) 是多种癌症的一个有吸引力的治疗靶点，但迄今为止还没有选择性 FGFR2 抑制剂被批准用于临床。在这里，我们报告了一系列新型选择性、不可逆 FGFR2 抑制剂的发现。代表性化合物可有效抑制 FGFR2 激酶活性，IC 值为 5.2 nM，并且对 FGFR1、FGFR3 和 FGFR4 的选择性分别为 >61、>34 和 >293 倍。在一组 416 种激酶中也表现出高选择性。基于细胞的研究表明，它能有效抑制 BaF3-FGFR2 细胞的增殖，IC 值为 1.4 nM，并且对 BaF3-FGFR1 和亲代 BaF3 细胞分别表现出 >70 倍和 >714 倍的选择性。更重要的是，有效抑制FGFR2信号通路，选择性抑制FGFR2驱动的癌细胞增殖，并诱导FGFR2驱动的癌细胞凋亡。综上所述，这项研究为进一步开发 FGFR2 靶向治疗药物提供了一种有效且高选择性的