3-苯氨羰基苯硼酸 | 397843-71-9

• 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-苯氨羰基苯硼酸
• 中文别名: 3-苯基氨甲酰基苯硼酸
• 英文名称: (3-(phenylcarbamoyl)phenyl)boronic acid
• 英文别名: 3-phenylaminocarbonylphenylboronic acid；3-(phenylcarbamoyl)phenylboronic acid；[3-(phenylcarbamoyl)phenyl]boronic acid
• CAS: 397843-71-9
• 化学式: C₁₃H₁₂BNO₃
• mdl: MFCD04115711
• 分子量: 241.054
• InChiKey: ZFEJFNWZHUMGRH-UHFFFAOYSA-N

物化性质

• 熔点：
  250-260°C
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 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：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  | 2-8°C |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
3-Phenylaminocarbonylphenylboronic 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-Phenylaminocarbonylphenylboronic acid
Ingredient name:
CAS number: 397843-71-9

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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: C13H12BNO3
Molecular weight: 241.1

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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

反应信息

• 作为反应物：
  描述：

  3-苯氨羰基苯硼酸 在 N-碘代丁二酰亚胺 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(4-amino-7-iodothiophene[3,2-c]pyridin-3-yl)-N-phenylbenzamide
  参考文献：
  名称：

  发现噻吩并[3,2 - c ]吡啶-4-胺作为新型布鲁顿酪氨酸激酶（BTK）抑制剂

  摘要：

  设计，合成和表征了一系列以噻吩并[3,2 - c ]吡啶-4-胺骨架为核心骨架的新型BTK抑制剂。在本文中，二十一种化合物在体外显示出对BTK酶的不同抑制活性，而化合物14g对BTK酶显示出最有效的抑制活性，IC 50值为12.8 nM。而且，化合物14g显示出相对良好的激酶选择性，并且随后在体内评估了其PK特性。这项工作确定了thieno [3,2 - c ] pyridin-4-amine衍生物是新型的BTK抑制剂，并验证了thieno [3,2 - c ] pyridin-4-amine支架在药物设计中的价值。

  DOI：

  10.1016/j.bmc.2015.05.043
• 作为产物：
  描述：

  3-羧基苯硼酸 、 苯胺 在 N,N-diethanolaminomethyl polystyrene 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 21.02h， 以81%的产率得到3-苯氨羰基苯硼酸
  参考文献：
  名称：

  通用固相方法用于硼酸的固定化，衍生化和树脂到树脂的转移反应。

  摘要：

  含硼酸的分子广泛用于生物学，医学和合成领域。然而，这些化合物往往难以通过溶液相方法处理。在此，该问题通过用于官能化硼酸的衍生化的第一种通用固相方法的开发来解决。该方法基于使用二乙醇胺树脂锚，该锚通过避免在酯化过程中彻底去除水的需要而促进了硼酸的固定。通过在室温下在无水溶剂中简单搅拌，可以在数分钟内将多种硼酸固定在N，N-二乙醇氨基甲基聚苯乙烯（DEAM-PS，1）上。通过（1）DEAM-PS负载的对甲苯基硼酸的（1）NMR分析显示了形成具有假定的NB配位的双环二乙醇胺硼酸酯的证据。通过紫外光谱研究了DEAM-PS树脂对相同型号硼酸的水解裂解。水解和附着显示在快速达到的平衡下发生，并且需要大量过量的水（> 32当量）以实现从DEAM-PS实际定量释放硼酸。尽管它们对水和醇具有相对的敏感性，但可以用甲酰基，溴甲基，羧基或氨基官能化的DEAM-PS结合的芳基硼酸以良好或极高的收率转化成各种胺，酰

  DOI：

  10.1021/jo0106501

文献信息

• Triazolopyridines
  申请人：Bayer Schering Pharma AG

  公开号：EP2343297A1

  公开（公告）日：2011-07-13

  The present invention relates to triazolopyridine compounds of general formula (I) which are Monopolar Spindle 1 kinase (Mps-1 or TTK) inhibitors: in which R1, R2, R3, R4, and R5 are as given in the description and in the claims, to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of proliferative diseases, as well as to intermediate compounds useful in the preparation of said compounds.

  本发明涉及一般式(I)的三唑吡啶化合物，其为单极纺锤体1激酶（Mps-1或TTK）抑制剂：其中R1、R2、R3、R4和R5如描述和索赔中所示，以及制备所述化合物的方法，包括所述化合物的药物组合物和组合物，用于制造用于治疗或预防增殖性疾病的药物组合物的用途，以及用于制备所述化合物的中间化合物。
• [EN] TRIAZOLOPYRIDINES<br/>[FR] TRIAZOLOPYRIDINES
  申请人：BAYER SCHERING PHARMA AG

  公开号：WO2011063908A1

  公开（公告）日：2011-06-03

  The present invention relates to triazolopyridine compounds of general formula (I) which are Monopolar Spindle 1 kinase (Mps-1 or TTK) inhibitors: Formula (I), in which R1, R2, R3, R4, and R5 are as given in the description and in the claims, to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis proliferative of diseases, as well as to intermediate compounds useful in the preparation of said compounds.

  本发明涉及通式（I）的三唑吡啶化合物，这些化合物是单极纺锤体1激酶（Mps-1或TTK）抑制剂： 公式（I），其中R1、R2、R3、R4和R5如描述和索赔中所示，以及制备所述化合物的方法，包括包含所述化合物的药物组合物和药物组合物，用于制造用于治疗或预防增殖性疾病的药物组合物的用途，以及用于制备所述化合物的中间化合物。
• Framework-Copper-Catalyzed C−N Cross-Coupling of Arylboronic Acids with Imidazole: Convenient and Ligand-Free Synthesis of N-Arylimidazoles
  作者：Nainamalai Devarajan、Palaniswamy Suresh

  DOI：10.1002/cctc.201600480

  日期：2016.9.21

  A convenient and environmentally benign synthesis of N‐arylimidazoles has been demonstrated by a straightforward reaction catalyzed by the unsaturated coordination sites of Cu in the copper terephthalate metal–organic framework (Cu(tpa)‐MOF). A series of N‐arylimidazoles has been synthesized in excellent yields by the C−N cross‐coupling reaction of arylboronic acids and imidazoles catalyzed by the

  N-芳基咪唑的一种便捷且对环境无害的合成已通过对苯二甲酸铜金属-有机骨架（Cu（tpa）-MOF）中Cu的不饱和配位点催化的简单反应得到证明。通过使用乙醇作为良性溶剂，Cu（tpa）-MOF催化的芳基硼酸和咪唑的C-N交叉偶联反应，已以高收率合成了一系列N-芳基咪唑。本发明的不含配体的催化体系在温和条件下可平稳运行，避免使用化学计量比的Cu试剂，可耐受许多官能团，具有广泛的底物范围，并且可与其他氮杂环一起使用。异质性测试的结果证明了催化剂的稳定性和非均质性，并且该催化剂可以重复使用几次而不会损失活性。
• 噻吩并[3,2-c]吡啶类化合物、其制备方法及 应用
  申请人：南京勇山生物科技有限公司

  公开号：CN104945411B

  公开（公告）日：2018-07-31

  本发明涉及一类噻吩并[3,2‑c]吡啶类化合物及其应用，其具有式（I）结构。本发明的结构如式（I）所示的化合物对布鲁顿激酶活性具有很好的抑制作用，本发明还涉及此类化合物在预防和/或治疗因BTK（Bruton酪氨酸激酶）活性抑制而改善的疾病中的应用。
• Convenient amidation of carboxyl group of carboxyphenylboronic acids
  作者：Julia Nowak-Jary

  DOI：10.1515/chempap-2015-0245

  日期：2016.1.9

  standard and necessary procedures in amide bond formation. In contrast to the usual methods, various new compounds, amides of APTES ((3-aminopropyl)triethoxysilane, 3-triethoxysilylpropylamine) and carboxyphenylboronic acids, as well as the amides of aniline and carboxyphenylboronic acids, were obtained in good yields by a one-step synthesis under mild conditions without using any coupling reagents or

  在酰胺键形成过程中，标准的和必要的方法是使用催化剂活化羧基使其朝亲核进攻和通过合适的保护基团保护其他官能团。与通常的方法相比，APTES的各种新化合物，APTES的酰胺（（3-氨基丙基）三乙氧基硅烷，3-三乙氧基甲硅烷基丙胺）和羧苯基硼酸，以及苯胺和羧苯基硼酸的酰胺可以通过以下方法得到高收率：在温和条件下进行步骤合成，无需使用任何偶联剂或其他催化剂。