3-(N-甲基甲酰氨)苯基硼酸 | 832695-88-2

• 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-(N-甲基甲酰氨)苯基硼酸
• 中文别名: 3-(N-甲基氨基羰基)苯硼酸；(3-(甲基氨基甲酰)苯基)硼酸；3-(N-甲基胺甲酰基)苯硼酸；3-甲基氨基甲酰苯硼酸；3-(N-甲基氨酰基)苯硼酸
• 英文名称: 3-(methylcarbamoyl)phenylboronic acid
• 英文别名: 3-(N-methylaminocarbonyl)phenylboronic acid；[3-(methylcarbamoyl)phenyl]boronic acid
• CAS: 832695-88-2
• 化学式: C₈H₁₀BNO₃
• mdl: MFCD04038918
• 分子量: 178.983
• InChiKey: FYFFPNFUVMBPRZ-UHFFFAOYSA-N

物化性质

• 熔点：
  114-124°C
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.54
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
3-(N-Methylaminocarbonyl)phenylboronic acid
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H315: Causes skin irritation
H317: May cause an allergic skin reaction
H318: Causes serious eye damage
May cause respiratory irritation
H335:
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
3-(N-Methylaminocarbonyl)phenylboronic acid
Ingredient name:
CAS number: 832695-88-2

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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: C8H10BNO3
Molecular weight: 179.0

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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

用途

3-(N-甲基甲酰氨基)苯基硼酸是苯基硼酸频哪醇酯类衍生物，广泛应用于医药化工领域。

制备

将3.0g (8.85mmol)七水合磷酸钾、1.50g (5.90mmol) 联硼酸频哪醇酯B2(pin)₂、12mg (0.015mmol) Xphos-Pd-G2和4mg (0.008mmol) Xphos依次加入反应瓶中，加入6mL乙醇搅拌均匀。再加入0.36mL (2.95mmol) 3-(N-甲基甲酰氨基)氯苯，在室温下反应1小时。反应液中加入5mL乙酸乙酯稀释，经硅藻土过滤后用乙酸乙酯洗涤，合并滤液，减压浓缩得到粗产物。通过硅胶柱层析分离，以石油醚-乙酸乙酯洗脱，最终获得3-(N-甲基甲酰氨基)苯基硼酸频哪醇酯。

水解

将制备的3-(N-甲基甲酰氨基)苯基硼酸频哪醇酯加入反应瓶中，滴加稀盐酸水解。溶液初始产生沉淀，随着反应进行沉淀逐渐消失，调节体系pH值至1。然后向溶液中滴加25％质量分数的氢氧化钠溶液，直至pH值达到13，搅拌1小时后分液。有机相用15mL质量分数为10%的NaOH溶液萃取两次，将水相合并，并用15mL四氢呋喃（THF）分别萃取碱液两次。将得到的碱液用稀盐酸调pH值至开始产生浑浊并逐渐形成絮状物，再调节pH值至5.0。使用70mL THF萃取水相，有机相旋干、提纯后获得3-(N-甲基甲酰氨基)苯基硼酸。

反应信息

• 作为反应物：
  描述：

  3-(N-甲基甲酰氨)苯基硼酸 在 N-氯代丁二酰亚胺 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以96%的产率得到3-氯-N-甲基苯甲酰胺
  参考文献：
  名称：

  10.1021/0l9029337

  摘要：

  DOI：

  10.1021/0l9029337
• 作为试剂：
  描述：

  N-甲基-3-溴苯甲酰胺 、 正丁基锂 、 硼酸三甲酯 、 盐酸 、 、 (4-bromophenyl)(1-trityl-1H-imidazol-4-yl)methanone 、 disodium;carbonate 在 四(三苯基膦)钯 乙酸乙酯 、 Brine 、 crude product 、 3-(N-甲基甲酰氨)苯基硼酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.83h， 以the title compound (6.89 g) was obtained as colorless powder crystals的产率得到4'-[1-hydroxy-(1H-imidazol-4-yl)ethyl]-N-methyl[1,1'-biphenyl]-3-carboxamide
  参考文献：
  名称：

  1-substituted phenyl-1-(1h-imidazol-4-yl) alcohols, process for producing the same and use thereof

  摘要：

  提供一种具有类固醇C17,20-裂解酶抑制活性并用作前列腺增生和乳腺癌等肿瘤的预防或治疗剂的组合物。该化合物的公式如下：其中R是氢原子或保护基，R1是较低的烷基或环烃基，R2是芳香族烃基（可选有取代基）或芳香族杂环基（可选有取代基），R3是可选有取代基的碳氢基团、羟基团、硫醇基团、氨基团、酰基或卤素原子，n是0到4的整数，其盐具有类固醇C17,20-裂解酶抑制活性，并且可用作前列腺增生和乳腺癌等肿瘤的预防或治疗剂。

  公开号：

  US06518257B1

文献信息

• Substrate Activity Screening:  A Fragment-Based Method for the Rapid Identification of Nonpeptidic Protease Inhibitors
  作者：Warren J. L. Wood、Andrew W. Patterson、Hiroyuki Tsuruoka、Rishi K. Jain、Jonathan A. Ellman

  DOI：10.1021/ja0547230

  日期：2005.11.1

  A new fragment-based method for the rapid development of novel and distinct classes of nonpeptidic protease inhibitors, Substrate Activity Screening (SAS), is described. This method consists of three steps: (1) a library of N-acyl aminocoumarins with diverse, low molecular weight N-acyl groups is screened to identify protease substrates using a simple fluorescence-based assay, (2) the identified N-acyl

  描述了一种新的基于片段的方法，用于快速开发新型和不同类别的非肽蛋白酶抑制剂，即底物活性筛选 (SAS)。该方法由三个步骤组成：(1) 筛选具有多种低分子量 N-酰基的 N-酰基氨基香豆素库，以使用简单的基于荧光的测定来鉴定蛋白酶底物，(2) 已鉴定的 N-酰基氨基香豆素底物通过快速类似物合成和评估进行优化，并且 (3) 优化的底物通过用已知机制的药效团直接替换氨基香豆素而转化为抑制剂。SAS 方法已成功应用于与自身免疫性疾病有关的半胱氨酸蛋白酶组织蛋白酶 S。在筛选 N-酰基氨基香豆素文库时鉴定出多种不同类别的非肽底物。两种非肽底物类别针对底物进行了优化，每个类别的切割效率提高了 8000 倍以上。然后将选择的非肽底物直接转化为对组织蛋白酶 S 具有纳摩尔亲和力的低分子量新型醛抑制剂。本研究证明了这种基于底物的快速鉴定和优化弱片段方法的独特特征和优点，并提供了框架用于开发针对许多不同蛋白酶的完全非肽抑制剂。
• CYCLOALKANE-1,3-DIAMINE DERIVATIVE
  申请人：Daiichi Sankyo Company, Limited

  公开号：US20210269454A1

  公开（公告）日：2021-09-02

  The present invention provides a compound or a pharmaceutically acceptable salt thereof having an inhibitory action on the interaction between menin and an MLL protein. The compound represented by the formula (1) or a pharmaceutically acceptable salt thereof. wherein, in the formula (1), the dotted circle, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , Ring Q 1 , W, m and n are each as defined in the description.

  本发明提供了一种具有对menin和MLL蛋白相互作用抑制作用的化合物或其药学上可接受的盐。该化合物由式（1）表示，或其药学上可接受的盐。 在式（1）中，虚线圈，R1，R2，R3，R4，R5，R6，R7，R8，环Q1，W，m和n的定义如描述中所述。
• Heterobicyclic pyrazole compounds and methods of use
  申请人：Blake F. James

  公开号：US20070238726A1

  公开（公告）日：2007-10-11

  Compounds of Formulas Ia and Ib, and stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting receptor tyrosine kinases and for treating disorders mediated thereby. Methods of using compounds of Formula Ia and Ib, and stereoisomers, geometric isomers, tautomers, solvates and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

  化合物Ia和Ib的结构，以及其立体异构体、几何异构体、互变异构体、溶剂合物、代谢物和药学上可接受的盐，可用于抑制受体酪氨酸激酶并治疗由此介导的疾病。公开了使用化合物Ia和Ib的结构，以及其立体异构体、几何异构体、互变异构体、溶剂合物和药学上可接受的盐的方法，用于体外、体内和体内诊断、预防或治疗哺乳动物细胞中的这类疾病，或相关的病理条件。
• [EN] COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS ET LEURS UTILISATIONS
  申请人：FOGHORN THERAPEUTICS INC

  公开号：WO2019152437A1

  公开（公告）日：2019-08-08

  The present disclosure features compounds useful for the treatment of BAF complex-related disorders.

  本公开涉及用于治疗BAF复合物相关疾病的化合物。
• Discovery of a series of 1H-pyrrolo[2,3-b]pyridine compounds as potent TNIK inhibitors
  作者：Bowen Yang、Qian Wu、Xiajuan Huan、Yingqing Wang、Yin Sun、Yueyue Yang、Tongchao Liu、Xin Wang、Lin Chen、Bing Xiong、Dongmei Zhao、Zehong Miao、Danqi Chen

  DOI：10.1016/j.bmcl.2020.127749

  日期：2021.2

  In an in-house screening, 1H-pyrrolo[2,3-b]pyridine scaffold was found to have high inhibition on TNIK. Several series of compounds were designed and synthesized, among which some compounds had potent TNIK inhibition with IC50 values lower than 1 nM. Some compounds showed concentration-dependent characteristics of IL-2 inhibition. These results provided new applications of TNIK inhibitors and new prospects

  在内部筛选中，发现1 H-吡咯并[2,3- b ]吡啶支架对TNIK具有高度抑制作用。设计并合成了一系列化合物，其中一些化合物具有强的TNIK抑制作用，IC 50值低于1 nM。一些化合物表现出浓度依赖性的IL-2抑制特性。这些结果提供了TNIK抑制剂的新应用以及TNIK作为药物靶标的新前景。