2-硼-4-溴-1H-吲哚-1-羧酸-1-(1,1-二甲基乙基)酯 | 957034-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 2-硼-4-溴-1H-吲哚-1-羧酸-1-(1,1-二甲基乙基)酯
• 英文名称: 4-bromo-1-(tert-butoxycarbonyl)-1H-indol-2-ylboronic acid
• 英文别名: (4-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid；[4-bromo-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boronic acid
• CAS: 957034-29-6
• 化学式: C₁₃H₁₅BBrNO₄
• 分子量: 339.981
• InChiKey: WWSBCMYHAIKIPV-UHFFFAOYSA-N

物化性质

• 沸点：
  488.3±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  71.7
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312+P330,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 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: 1-BOC-4-bromo-indole-2-boronic acid
Synonyms: 4-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-ylboronic acid; 1-Boc-4-bromo-2-indoleboronic acid

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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: 1-BOC-4-bromo-indole-2-boronic acid
CAS number: 957034-29-6

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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.
Store in closed vessels, under −20◦C.
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: C13H15BBrNO4
Molecular weight: 340.0

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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, 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：

  2-硼-4-溴-1H-吲哚-1-羧酸-1-(1,1-二甲基乙基)酯 、 3-氟溴苄 在 trans-bromo(N-succinimidyl)-bis(triphenylphosphine)palladium(II) 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以60%的产率得到4-bromo-2-(3-fluoro-benzyl)-indole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Palladium-catalyzed benzylation of N-Boc indole boronic acids

  摘要：

  The direct benzylation of indole 2-boronic acid can be efficiently achieved using trans-PdBr-(N-Succ)(PPh(3))(2), alleviating the need for strong bases or toxic organotin reagents. Under these reaction conditions substituted indole-2-boronic acids and substituted benzyl bromides are cross-coupled to afford aryl(indolo)methanes in good yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.124
• 作为产物：
  描述：

  4-溴吲哚-1-羧酸叔丁酯 在 硼酸三异丙酯 、 lithium diisopropyl amide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-硼-4-溴-1H-吲哚-1-羧酸-1-(1,1-二甲基乙基)酯
  参考文献：
  名称：

  三恶唑啉/ Cu（II）催化的吲哚不对称分子内弗里德-克来夫茨烷基化反应

  摘要：

  描述了三恶唑啉/铜（II）催化的吲哚分子内Friedel-Crafts烷基化反应。这种成环法可轻松获得ee高达90％且产率高达99％的多环吲哚衍生物。

  DOI：

  10.1016/j.tet.2009.06.071

文献信息

• Identification of potent ITK inhibitors through focused compound library design including structural information
  作者：Matthias Herdemann、Isabelle Heit、Frank-Uwe Bosch、Gianluca Quintini、Claudia Scheipers、Alexander Weber

  DOI：10.1016/j.bmcl.2010.09.119

  日期：2010.12

  A series of novel compound libraries inhibiting interleukin-2 inducible T cell kinase (ITK) were designed, synthesized and evaluated. In the first design cycle two library scaffolds were identified showing low micromolar inhibition of ITK. Further iterative design cycles including crystal structure information of ITK and structurally related kinases led to the identification of indolylindazole and indolylpyrazolopyridine compounds with low nanomolar ITK inhibition. (C) 2010 Elsevier Ltd. All rights reserved.
• Trisoxazoline/Cu(II)-catalyzed asymmetric intramolecular Friedel–Crafts alkylation reaction of indoles
  作者：Jiao-Long Zhou、Meng-Chun Ye、Xiu-Li Sun、Yong Tang

  DOI：10.1016/j.tet.2009.06.071

  日期：2009.8

  Intramolecular Friedel–Crafts alkylation reaction of indoles catalyzed by trisoxazoline/copper(II) is described. This annulation provides an easy access to polycyclic indole derivatives with up to 90% ee in up to 99% yield.

  描述了三恶唑啉/铜（II）催化的吲哚分子内Friedel-Crafts烷基化反应。这种成环法可轻松获得ee高达90％且产率高达99％的多环吲哚衍生物。
• Palladium-catalyzed benzylation of N-Boc indole boronic acids
  作者：Aaron M. Kearney、Adrienne Landry-Bayle、Laurent Gomez

  DOI：10.1016/j.tetlet.2010.02.124

  日期：2010.4

  The direct benzylation of indole 2-boronic acid can be efficiently achieved using trans-PdBr-(N-Succ)(PPh(3))(2), alleviating the need for strong bases or toxic organotin reagents. Under these reaction conditions substituted indole-2-boronic acids and substituted benzyl bromides are cross-coupled to afford aryl(indolo)methanes in good yield. (C) 2010 Elsevier Ltd. All rights reserved.