1-甲基-4-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-1H-吲哚 | 898289-06-0

• 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 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-甲基-4-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-1H-吲哚
• 英文名称: 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• 英文别名: 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole
• CAS: 898289-06-0
• 化学式: C₁₅H₂₀BNO₂
• 分子量: 257.14
• InChiKey: CBEYYYCGOCYJIK-UHFFFAOYSA-N

物化性质

• 熔点：
  94.5-96.5
• 沸点：
  391.3±15.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 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-Methylindol-4-boronic acid, pinacol ester
Synonyms: 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole

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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-Methylindol-4-boronic acid, pinacol ester
CAS number: 898289-06-0

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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: C15H20BNO2
Molecular weight: 257.1

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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：

  1-甲基-4-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-1H-吲哚 在 copper(I) bromide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  铜促进硼酯和二氮杂环丁酮的 C-N 偶联：一种制备芳基脲的方法

  摘要：

  描述了一种新的铜促进硼酯和二叔丁基二氮杂环丁酮之间的 C-N 偶联。在温和条件下可以很容易地获得多种芳基脲，产率高达 92%。

  DOI：

  10.1021/acs.orglett.1c03468
• 作为产物：
  描述：

  4-溴吲哚 在 palladium diacetate 、 2-(二环己基膦基)联苯 sodium hydride 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 1-甲基-4-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-1H-吲哚
  参考文献：
  名称：

  通过钯（0）催化溴化1 H-吲哚与'品那高硼烷'的硼化反应方便地合成1 H-吲哚-1-基硼酸酯

  摘要：

  从相应的溴吲哚底物2和频哪醇硼烷（pinBH）作为硼化剂，阐述了原子经济Pd 0催化的一系列频哪醇型吲哚硼酸酯3的合成。最佳催化剂体系由[Pd（OAc）2 ]与邻位取代的联苯膦配体L-3的1：2混合物组成（方案4，表）。我们的合成方案适用于在不同官能团存在下，催化剂负载量仅为Pd的1 mol％的情况下，快速进行制备级合成1-取代的吲哚基硼酸酯3a - h的方法。

  DOI：

  10.1002/hlca.200690097

文献信息

• INHIBITORS OF FIBROBLAST ACTIVATION PROTEIN
  申请人：Praxis Biotech LLC

  公开号：US20190185451A1

  公开（公告）日：2019-06-20

  Compounds and compositions for modulating fibroblast activation protein (FAP) are described. The compounds and compositions may find use as therapeutic agents for the treatment of diseases, including hyperproliferative diseases.

  描述了用于调节成纤维细胞活化蛋白（FAP）的化合物和组合物。这些化合物和组合物可能被用作治疗疾病的治疗剂，包括高增殖性疾病。
• Rhodium-Catalyzed Borylation of Aryl 2-Pyridyl Ethers through Cleavage of the Carbon–Oxygen Bond: Borylative Removal of the Directing Group
  作者：Hirotaka Kinuta、Mamoru Tobisu、Naoto Chatani

  DOI：10.1021/ja511622e

  日期：2015.2.4

  diboron reagent results in the formation of arylboronic acid derivatives via activation of the C(aryl)-O bonds. The straightforward synthesis of 1,2-disubstituted arenes was enabled through catalytic ortho C-H bond functionalization directed by the 2-pyridyloxy group followed by substitution of this group with a boryl group. Several control experiments revealed that the presence of a sp(2) nitrogen

  芳基 2-吡啶基醚与二硼试剂的铑催化反应导致通过活化 C(芳基)-O 键形成芳基硼酸衍生物。1,2-二取代芳烃的直接合成是通过由 2-吡啶氧基引导的催化邻位 CH 键官能化，然后用硼基取代该基团来实现的。几个对照实验表明，在底物的 2 位存在 sp(2) 氮原子和使用基于硼的试剂对于芳基相对惰性的 C(芳基)-O 键的活化至关重要。 2-吡啶基醚。
• [EN] SELECTIVE INHIBITORS OF CLINICALLY IMPORTANT MUTANTS OF THE EGFR TYROSINE KINASE<br/>[FR] INHIBITEURS SÉLECTIFS DE MUTANTS CLINIQUEMENT IMPORTANTS DE LA TYROSINE KINASE DE L'EGFR
  申请人：CS PHARMATECH LTD

  公开号：WO2019010295A1

  公开（公告）日：2019-01-10

  The present invention provides compounds of Formula (I) or a subgeneric structure or species thereof, or a pharmaceutically acceptable salt, ester, solvate, and/or prodrug thereof, and methods and compositions for treating or ameliorating abnormal cell proliferative disorders, such as cancer, wherein A, R2, R3, R10, E1, E2, E3, Y, and Z are as defined herein.

  本发明提供了式（I）的化合物或其亚类结构或种属，或其药学上可接受的盐、酯、溶剂化合物和/或前药，以及用于治疗或改善异常细胞增殖性疾病，如癌症的方法和组合物，其中A、R2、R3、R10、E1、E2、E3、Y和Z如本文所定义。
• Uncharged nucleoside inhibitors of β-1,4-galactosyltransferase with activity in cells
  作者：Jingqian Jiang、Varsha Kanabar、Beatriz Padilla、Francis Man、Simon C. Pitchford、Clive P. Page、Gerd K. Wagner

  DOI：10.1039/c5cc09289b

  日期：——

  5-Substituted uridine derivatives are uncharged galactosyltransferase inhibitors that reduce PSGL-1 expression in human monocytes.

  5-取代尿苷衍生物是无电荷的半乳糖转移酶抑制剂，可以降低人单核细胞中PSGL-1的表达。
• Catalytic (3 + 2) annulation of donor–acceptor aminocyclopropane monoesters and indoles
  作者：Vincent Pirenne、Emma G. L. Robert、Jerome Waser

  DOI：10.1039/d1sc01127h

  日期：——

  The efficient catalytic activation of donor–acceptor aminocyclopropanes lacking the commonly used diester acceptor is reported here in a (3 + 2) dearomative annulation with indoles. Bench-stable tosyl-protected aminocyclopropyl esters were converted into cycloadducts in 46–95% yields and up to 95 : 5 diastereomeric ratio using catalytic amounts of triethylsilyl triflimide. Tricyclic indoline frameworks

  缺少常用的二酯受体的供体-受体氨基环丙烷的有效催化活化在此处用吲哚进行的（3 + 2）脱芳香环中进行了报道。使用催化量的三乙基甲硅烷基三氟甲磺酸酯，将对位稳定的甲苯磺酰基保护的氨基环丙基酯以46-95％的收率和高达95：5的非对映体比例转化为环加合物。获得了包含四个立体生成中心（包括全碳四元中心）的三环二氢吲哚骨架。