2-甲基-5-硝基苯硼酸频哪醇酯 | 957062-84-9

• 物质功能分类: 表面活性剂 - 非离子表面活性剂 - 多元醇酯型
• 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-甲基-5-硝基苯硼酸频哪醇酯
• 中文别名: 2-甲基-5-硝基苯硼酸频那醇酯
• 英文名称: 4,4,5,5-tetramethyl-2-(2-methyl-5-nitrophenyl)-1,3,2-dioxaborolane
• CAS: 957062-84-9
• 化学式: C₁₃H₁₈BNO₄
• 分子量: 263.101
• InChiKey: LYFUUPOOXAXEEP-UHFFFAOYSA-N

物化性质

• 沸点：
  378.9±35.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Methyl-5-nitrophenylboronic acid, pinacol ester
Synonyms: 4,4,5,5-Tetramethyl-2-(2-methyl-5-nitrophenyl)-1,3,2-dioxaborolane

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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-Methyl-5-nitrophenylboronic acid, pinacol ester
CAS number: 957062-84-9

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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.
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
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C13H18BNO4
Molecular weight: 263.1

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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, nitrogen oxides.

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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

简介

2-甲基-5-硝基苯硼酸频那醇酯是一种苯硼酸酯类化合物，对氧化剂较为敏感，化学稳定性较差。该物质在受热或强光照射时容易发生变质分解。

制备

将苯胺（3 毫摩尔）与 14% HBr（6 mL）的混合物冷却至 0 °C，然后缓慢加入 NaNO2（3 毫摩尔、1.1 当量）在水（2.4 mL）中的溶液。在此过程中需注意不要使温度超过 0 °C。将反应混合物于 0 °C 下搅拌反应 30 分钟后，在室温下使用吸管快速将其加入含有 B2pin2（6 毫摩尔、2 当量）和 NaOAc（6 毫摩尔、2 当量）的甲醇（6 mL）溶液中。所得混合物于室温下搅拌 1 小时。

反应结束后，通过减压浓缩除去甲醇，然后将残余物用水（30 mL）稀释，并用二氯甲烷（3 × 30 mL）萃取水相。合并有机层并使用 Na2SO4 干燥后，蒸发得到粗产品。最后，通过硅胶柱色谱法分离纯化即可获得 2-甲基-5-硝基苯硼酸频那醇酯。

反应信息

• 作为反应物：
  描述：

  2-甲基-5-硝基苯硼酸频哪醇酯 在 N-羟基-7-氮杂苯并三氮唑 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 铁粉 、 sodium carbonate 、 potassium carbonate 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 八甲基环四硅氧烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 N-(3-(5-cyano-6-(piperazine-1-yl)pyridin-3-yl)-4-methylphenyl)-6-(trifluoromethyl)pyridazine-4-carboxamide trifluoroacetate
  参考文献：
  名称：

  [EN] COMPOUNDS AND COMPOSITIONS AS KINASE INHIBITORS
  [FR] COMPOSÉS ET COMPOSITIONS INHIBITEURS DE KINASES

  摘要：

  本发明提供了如下所述的化合物(I)和(II)，以及其盐，并且这些化合物用于治疗与Raf激酶活性相关的疾病的治疗用途。该发明还提供了包含这些化合物的药物组合物，以及包含这些化合物和治疗协同剂的组合物。

  公开号：

  WO2016038583A1
• 作为产物：
  描述：

  4-硝基甲苯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 potassium acetate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 32.0h， 生成 2-甲基-5-硝基苯硼酸频哪醇酯
  参考文献：
  名称：

  6-氨基-1-羟基-2,1-苯并氧硼杂环戊烷的实际合成：DNDI-6148 的关键中间体

  摘要：

  内脏利什曼病 (VL) 是一种与贫困相关、被忽视的寄生性疾病，在世界多个地区流行，如果不及时治疗可能致命。迫切需要一种更好、更实惠的 VL 治疗方法。 DNDI-6148 是一种有前途的候选药物，正在评估其治疗 VL 的效果；然而，目前生产 DNDI-6148 关键中间体 6-氨基-1-羟基-2,1-苯并氧杂硼杂环硼烷的工艺成本昂贵且难以扩大规模。在这里，我们描述了两种从廉价且容易获得的原材料合成 6-氨基-1-羟基-2,1-苯并氧硼杂硼烷的实用方法。从 4-甲苯腈开始，第一种方法是涉及霍夫曼重排的五步序列，总产率为 40%。第二种方法以2-甲基-5-硝基苯胺为起始原料，以苯胺硼化和连续流动氢化为关键步骤，总收率为46%。两条路线都绕过了 1-羟基-2,1-苯并氧杂硼杂硼烷的硝化，这具有挑战性且规模化成本昂贵。特别是，第二种方法由于温和的操作条件和简便的隔离过程而更加实用和可扩展。

  DOI：

  10.1021/acs.oprd.4c00031

文献信息

• [EN] COMPOUNDS AND COMPOSITIONS AS RAF KINASE INHIBITORS<br/>[FR] COMPOSÉS ET COMPOSITIONS COMME INHIBITEURS DE PROTÉINES KINASES
  申请人：NOVARTIS AG

  公开号：WO2016038582A1

  公开（公告）日：2016-03-17

  The present invention provides compounds of Formula (I) and (II) as described herein, and salts thereof, and therapeutic uses of these compounds for treatment of disorders associated with Raf kinase activity. The invention further provides pharmaceutical compositions comprising these compounds, and compositions comprising these compounds and a therapeutic co-agent.

  本发明提供了如下所述的化合物(I)和(II)，以及其盐，并且提供了这些化合物用于治疗与Raf激酶活性相关的疾病的治疗用途。该发明还提供了包含这些化合物的药物组合物，以及包含这些化合物和治疗协同剂的组合物。
• CML THERAPEUTIC AGENTS WITH REDUCED DRUG-RESISTANCE AND SIDE-EFFECT COMPRISING 1,6-DISUBSTITUTED INDOLE COMPOUNDS
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY

  公开号：US20180050036A1

  公开（公告）日：2018-02-22

  The present invention relates to a therapeutic agent for chronic myelogenous leukemia with reduced drug-resistance and side-effects containing a 1,6-disubstituted indole compound.

  本发明涉及一种治疗慢性髓细胞白血病的治疗剂，含有一种减少药物抗性和副作用的1,6-二取代吲哚化合物。
• 4-SUBSTITUTED-(3-SUBSTITUTED-1H-PYRAZOLE-5-AMINO)-PYRIMIDINE DERIVATIVES HAVING ACTIVITY OF INHIBITING PROTEIN KINASE AND USE THEREOF
  申请人：ZHEJIANG HISUN PHARMACEUTICAL CO., LTD.

  公开号：US20140378488A1

  公开（公告）日：2014-12-25

  Provided are derivatives substituted by urea associated with 4-substituted-(3-substituted-1H-pyrazole-5-amino)-pyrimidine-2-amino of formula (I), wherein these compounds may selectively regulate or inhibit an information transmission process controlled by natural or variant tyrosine kinase. Also provided are preparation methods and uses of the compounds.

  提供了与4-取代-(3-取代-1H-吡唑-5-氨基)-嘧啶-2-氨基的脲取代物相关的衍生物，其化学式为(I)，这些化合物可以选择性地调节或抑制由天然或变种酪氨酸激酶控制的信息传递过程。还提供了这些化合物的制备方法和用途。
• Synthesis of Amino- and Hydroxymethyl Benzoxaboroles: Prominent Scaffolds for Further Functionalization
  作者：Rodrigo S. Fuscaldo、Pedro H. V. Vontobel、Eduam O. Boeira、Angélica V. Moro、Jessie S. da Costa

  DOI：10.1002/ejoc.201900013

  日期：2019.3.14

  The development of a short, simple, and efficient synthesis of amino‐ and hydroxymethyl‐substituted benzoxaboroles is described. The key step was the early stage incorporation of the boron by the borylation of an aniline. The formed boronates were then elaborated to the final products in two additional steps, in good yields.

  本文描述了一种短，简单而有效的合成氨基和羟甲基取代的苯并氧杂硼酸的方法的开发。关键步骤是通过苯胺的硼化使硼早期掺入。然后将形成的硼酸盐分两步精加工成最终产品，收率很高。
• NOVEL 1,6-DISUBSTITUTED INDOLE COMPOUNDS AS PROTEIN KINASE INHIBITORS
  申请人：Sim Tae Bo

  公开号：US20120271048A1

  公开（公告）日：2012-10-25

  Disclosed are a 1,6-substituted indole compound having a protein kinase inhibition activity, a pharmaceutically acceptable salt, and a pharmaceutical composition for prevention and treatment of cancers caused by abnormal cell growth comprising the compound as an effective ingredient. Since the novel indole compound exhibits superior inhibition activity against various protein kinases involved in growth factor signal transduction, it is useful as an agent for preventing or treating cancers caused by abnormal cell growth.

  公开了一种具有蛋白激酶抑制活性的1,6-取代吲哚化合物，其包括一种药用可接受的盐和一种药物组合物，用于预防和治疗由异常细胞生长引起的癌症，其中该化合物作为有效成分。由于这种新型吲哚化合物表现出对参与生长因子信号转导的各种蛋白激酶具有优越的抑制活性，因此它可用作预防或治疗由异常细胞生长引起的癌症的药物。