2-(2,2,2-三甲基乙酰氨基)苯硼酸 | 146140-95-6

• 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-(2,2,2-三甲基乙酰氨基)苯硼酸
• 中文别名: 2-(叔丁羰氨基)苯硼酸；2-(2,2,2-三甲基乙酰氨基)苯硼酸,95%
• 英文名称: 2-pivaloylaminophenyl boronic acid
• 英文别名: o-pivaloylaminophenylboronic acid；(2-pivaloylaminobenzene)boronic acid；N-(2-boronophenyl)-2,2-dimethylpropanamide；2-(tert-Butylcarbonylamino)phenylboronic acid；[2-(2,2-dimethylpropanoylamino)phenyl]boronic acid
• CAS: 146140-95-6
• 化学式: C₁₁H₁₆BNO₃
• mdl: MFCD01114645
• 分子量: 221.064
• InChiKey: MXRAJVMTCAUABO-UHFFFAOYSA-N

物化性质

• 熔点：
  268-271℃
• 密度：
  1.13±0.1 g/cm3(Predicted)
• 溶解度：
  甲醇
• 稳定性/保质期：
  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2931900090
• 危险类别：
  IRRITANT
• 安全说明：
  S26
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H319
• 储存条件：
  保存方法：密闭存放于阴凉、通风干燥处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(tert-Butylcarbonylamino)phenylboronic acid
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H319: Causes serious eye irritation
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.
Ingredient name: 2-(tert-Butylcarbonylamino)phenylboronic acid
CAS number: 146140-95-6

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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.

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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: C11H16BNO3
Molecular weight: 221.1

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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

光谱试剂

反应信息

• 作为反应物：
  描述：

  2-(2,2,2-三甲基乙酰氨基)苯硼酸 在 四(三苯基膦)钯 、 吡啶盐酸盐 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 甲苯 为溶剂， 反应 52.5h， 生成 11-chloro-10H-indolo[3,2-b]quinoline
  参考文献：
  名称：

  苯并-δ-咔啉，隐肾上腺素及其盐的新合成：δ-咔啉，苯并-δ-咔啉和隐肾上腺素的体外细胞毒性，抗血浆和抗胰蛋白酶活性。

  摘要：

  该论文的第一部分描述了苯并-δ-咔啉，隐肾上腺素及其盐的新合成方法。该策略基于卤素原子与杂环交叉耦合之间的关联。它是完全收敛的和区域选择性的，总产率从27％到70％令人感兴趣。还提出了喹啉系列的卤素舞蹈机理。还描述了潜在的抗疟化合物的形式合成和11-异丙基隐油菜碱的第一个全合成。在第二部分中，评估了苯并-δ-咔啉和δ-咔啉对哺乳动物细胞的细胞毒活性以及对恶性疟原虫和克氏锥虫的活性，以研究其结构-活性关系。对于苯并-δ-咔啉，N-5处的甲基化会增加细胞毒性和抗寄生虫活性。C-11上的进一步烷基化通常会增加细胞毒性活性，但不会增加抗寄生虫活性，隐血藤本和11-甲基隐油菜碱在两种寄生虫中活性最高。利用吲哚喹啉发色团的荧光，通过荧光显微术将隐氯平定位在含有寄生虫DNA的结构中，这表明这些化合物通过与寄生虫DNA相互作用而发挥作用，这是针对隐伏平在黑色素瘤细胞上提出的。对于δ-咔啉，N-1处的甲基化

  DOI：

  10.1021/jm0010419
• 作为产物：
  描述：

  N-(2-溴苯基)-2,2-二甲基丙酰胺 在 正丁基锂 、 硼酸三异丙酯 作用下， 以 四氢呋喃 为溶剂， 反应 6.08h， 以98.6%的产率得到2-(2,2,2-三甲基乙酰氨基)苯硼酸
  参考文献：
  名称：

  [EN] PROCESSES AND INTERMEDIATES FOR PRODUCING AMINOBENZIMIDAZOLE UREAS
  [FR] PROCÉDÉS ET PRODUITS INTERMÉDIAIRES POUR PRODUIRE DES URÉES D'AMINOBENZIMIDAZOLE

  摘要：

  公开号：

  WO2009061875A3

文献信息

• Regioexhaustive Functionalization of the Carbocyclic Core of Isoquinoline: Concise Synthesis of Oxoaporphine Core and Ellipticine
  作者：Tibor Soós、Dániel Horváth、Frigyes Domonyi、Roberta Palkó、Andrea Lomoschitz

  DOI：10.1055/s-0037-1609153

  日期：2018.6

  functionalization of the carbocyclic core of the isoquinoline. This regioexhaustive approach employs electrophilic halogenation as a toolbox methodology and delivers highly decorated intermediates that can be further elaborated toward medicinally relevant building blocks or natural products. A general and versatile strategy has been developed for the functionalization of the carbocyclic core of the isoquinoline. This

  摘要 已经开发了用于异喹啉碳环核心功能化的通用且通用的策略。这种区域穷举性方法采用亲电子卤化作为工具箱方法，并提供了装饰精美的中间体，可以将其进一步加工成与医学相关的构件或天然产物。 已经开发了用于异喹啉碳环核心功能化的通用且通用的策略。这种区域穷举性方法采用亲电子卤化作为工具箱方法，并提供了装饰精美的中间体，可以将其进一步加工成与医学相关的构件或天然产物。
• A new convergent synthesis of alpha - substituted - beta - carbolines
  作者：P. Rocca、F. Marsais、A. Godard、G. Queguiner

  DOI：10.1016/s0040-4020(01)90161-9

  日期：1993.4

  New convergent synthesis of natural α-substituted-β-carbolines through metalations, cross-couplings and intramolecular substitution via (2-aminobenzene)-boronic acid, arylstannanes and ortho-fluoroiodopyridines.

  通过（2-氨基苯）-硼酸，芳基锡烷和邻氟碘吡啶的金属化，交叉偶联和分子内取代，新的聚合合成天然α-取代-β-咔啉。
• A new synthesis of α-substituted δ-carbolines
  作者：Erwan Arzel、Patrick Rocca、Francis Marsais、Alain Godard、Guy Quéguiner

  DOI：10.1002/jhet.5570340418

  日期：1997.7

  The paper describes a new general synthesis of α-substituted δ-carbolines based on key steps such as metalation, cross-coupling and cyclization.

  本文基于金属化，交叉偶联和环化等关键步骤，描述了一种新的α-取代的δ-咔啉的一般合成方法。
• Gyrase inhibitors and uses thereof
  申请人：——

  公开号：US20040235886A1

  公开（公告）日：2004-11-25

  The present invention relates to compounds which inhibit bacterial gyrase and/or Topo IV and pharmaceutically acceptable compositions comprising said compounds. These compounds, and compositions thereof, are useful in treating bacterial infection. Accordingly, the present invention also relates to methods for treating bacterial infections in mammals.

  本发明涉及抑制细菌旋转酶和/或Topo IV的化合物以及包含该类化合物的药学上可接受的组合物。这些化合物及其组合物在治疗细菌感染方面具有用途。因此，本发明还涉及治疗哺乳动物细菌感染的方法。
• Synthesis of novel fused azecine ring systems through application of the tert-amino effect
  作者：Petra Dunkel、György Túrós、Attila Bényei、Krisztina Ludányi、Péter Mátyus

  DOI：10.1016/j.tet.2010.02.014

  日期：2010.3

  Novel fused azecine ring systems were synthesized via the microwave-assisted thermal isomerization of terphenyl or biphenyl-pyridazine compounds possessing a vinyl and a tert-amino group, through application of a new extension of the tert-amino effect. Substrates for the ring closure were prepared from ortho-dihalobenzene or pyridazinone by consecutive Suzuki couplings with ortho-sec-amino- and formylphenylboronic

  新的稠合环azecine系统是经由具有的乙烯基和三联苯或联苯哒嗪化合物的微波辅助的热异构化合成叔-氨基，通过的一个新的扩展的应用叔氨基的效果。从制备用于环合衬底邻-dihalobenzene或哒嗪酮通过连续Suzuki偶联与邻-仲丁基氨基甲酰基苯基和酸，然后所获得的醛的Knoevenagel缩合。