5-吲哚硼酸频哪醇酯 | 269410-24-4

• 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: 5-吲哚硼酸频哪醇酯
• 中文别名: 1H-吲哚-5-硼酸频哪醇酯；吲哚-5-硼酸频哪酯；5-(4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基)-1H-吲哚；5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)-1H-吲哚
• 英文名称: 5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• 英文别名: 5-indoleboronic acid pinacol ester；5-indolylboronic acid pinacol ester；5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-(1H)-indole；indole-5-boronic acid pinacol ester；5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• CAS: 269410-24-4
• 化学式: C₁₄H₁₈BNO₂
• mdl: MFCD03789263
• 分子量: 243.113
• InChiKey: FATPQDPUKVVCLT-UHFFFAOYSA-N

物化性质

• 熔点：
  120-125 °C (lit.)
• 沸点：
  396.0±15.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  避免与氧化物、不相容的材料、矿物酸和卤素接触。

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36,S36/37/39
• 危险类别码：
  R22,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933990090
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  保存方法：密闭、阴凉、干燥处

SDS

Name:	5-(4 4 5 5-Tetramethyl-1 3 2-dioxaborolan- 2-yl)-1H-indole Material Safety Data Sheet
Synonym:	Indole-5-boronic acid pinacol este
CAS:	269410-24-4

Section 1 - Chemical Product MSDS Name:5-(4 4 5 5-Tetramethyl-1 3 2-dioxaborolan- 2-yl)-1H-indole Material Safety Data Sheet
Synonym:Indole-5-boronic acid pinacol este

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
269410-24-4	5-(4,4,5,5-Tetramethyl-1,3,2-dioxaboro		unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 269410-24-4: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: pale yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 114 - 116.5 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble.
Specific Gravity/Density:
Molecular Formula: C14H18BNO2
Molecular Weight: 243.11

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, halogens, mineral acids.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide, oxides of boron.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 269410-24-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan- 2-yl)-1H-indole - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 269410-24-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 269410-24-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 269410-24-4 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-吲哚硼酸频哪醇酯 在 Oxone 、 potassium phosphate 、 2-萘硼酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 5-羟基吲哚
  参考文献：
  名称：

  通过硼酸选择性相转移实现芳基有机硼系统的化学选择性氧化†

  摘要：

  我们报道了含有两个可氧化硼基团的芳基有机硼系统的直接化学选择性布朗型氧化。碱性双相反应条件能够在硼酸频哪醇 (BPin) 酯存在下选择性形成硼酸三羟基硼酸酯并进行相转移，同时避免形态平衡。光谱研究验证了有机硼物质的碱促进相选择性辨别。这种现象在多种有机硼化合物中普遍存在，也可用于反转传统的保护基策略，使 BMIDA 物质能够在通常更具反应性的 BPin 底物上进行化学选择性氧化。我们还证明了二硼酸系统的选择性氧化具有可先验预测的化学选择性。该方法的实用性通过化学选择性氧化亲核试剂偶联的开发来例证。

  DOI：

  10.1039/c6sc04014d
• 作为产物：
  描述：

  5-羟基吲哚 在 potassium acetate 、 三乙胺 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 18.0h， 生成 5-吲哚硼酸频哪醇酯
  参考文献：
  名称：

  钯催化的甲磺酸烷基酯和甲苯磺酸酯的硼化反应及其在一锅顺序铃木-宫浦联芳的合成中的应用

  摘要：

  一锅之巅！描述了芳基甲苯磺酸盐和甲磺酸盐的第一个钯催化的硼化反应。反应条件温和，并具有出色的官能团相容性（例如，R = CN，CHO，COOMe，C（O）R，NH 2或NH-吲哚；请参见方案）。Pd / MeO-CM-phos可在不对称联芳烃的制备中进行一锅法依次反应。

  DOI：

  10.1002/chem.201100361

文献信息

• [EN] BCR-ABL TYROSINE-KINASE LIGANDS CAPABLE OF DIMERIZING IN AN AQUEOUS SOLUTION, AND METHODS OF USING SAME<br/>[FR] LIGANDS DE TYROSINE-KINASE BCR-ABL CAPABLES DE SE DIMÉRISER DANS UNE SOLUTION AQUEUSE, ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：COFERON INC

  公开号：WO2015106292A1

  公开（公告）日：2015-07-16

  Described herein are monomers capable of forming a biologically useful multimer when in contact with one, two, three or more other monomers in an aqueous media. In one aspect, such monomers may be capable of binding to another monomer in an aqueous media (e.g. invivo) to form a multimer (e.g. a dimer). Contemplated monomers may include a ligand moiety, a linker element, and a connector element that joins the ligand moiety and the linker element. In an aqueous media, such contemplated monomers may join together via each linker element and may thus be capable of modulating one or more biomolecules substantially simultaneously, e.g., modulate two or more binding sites on a Bcr-Abl tyrosine kinase.

  本文描述了一种单体，当与水性介质中的另一个、两个、三个或更多其他单体接触时，能够形成生物学上有用的多聚体。在一个方面，这种单体可能能够在水性介质（例如体内）中与另一个单体结合以形成多聚体（例如二聚体）。考虑到的单体可能包括配体基团、连接元素和连接配体基团与连接元素的连接元素。在水性介质中，这些考虑到的单体可以通过每个连接元素结合在一起，因此可以同时调节一个或多个生物分子，例如，调节Bcr-Abl酪氨酸激酶上的两个或更多结合位点。
• Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles
  作者：Justin S. Marcum、Courtney C. Roberts、Rajith S. Manan、Tia N. Cervarich、Simon J. Meek

  DOI：10.1021/jacs.7b08575

  日期：2017.11.8

  Catalytic enantioselective addition of N-heteroarenes to terminal and internal 1,3-dienes is reported. Reactions are promoted by 5 mol % of Rh catalyst supported by a new chiral pincer carbodicarbene ligand that delivers allylic substituted arenes in up to 95% yield and up to 98:2 er. Mechanistic and X-ray evidence is presented that supports that the reaction proceeds via a Rh(III)-η3-allyl.

  据报道N-杂芳烃向末端和内部1，3-二烯的催化对映选择性加成。5 mol％的Rh催化剂促进了反应，该催化剂由新型手性钳碳二碳烯配体支撑，该配体可提供高达95％的收率和高达98：2 er的烯丙基取代的芳烃。机械和透视证据呈现支持经由铑（III）-η反应进行3 -烯丙基。
• [EN] AZOLE COMPOUNDS AS PIM INHIBITORS<br/>[FR] COMPOSÉS D'AZOLE UTILISÉS EN TANT QU'INHIBITEURS DES PIM
  申请人：AMGEN INC

  公开号：WO2012129338A1

  公开（公告）日：2012-09-27

  The invention relates to bicyclic compounds of formulas I and Ia, and salts thereof. In some embodiments, the invention relates to inhibitors or modulators of Pim-1 and/or Pim-2, and/or Pim-3 protein kinase activity or enzyme function. In still further embodiments, the invention relates to pharmaceutical compositions comprising compounds disclosed herein, and their use in the prevention and treatment of Pim kinase related conditions and diseases, preferably cancer.

  该发明涉及公式I和Ia的双环化合物及其盐。在某些实施例中，该发明涉及Pim-1和/或Pim-2和/或Pim-3蛋白激酶活性或酶功能的抑制剂或调节剂。在更进一步的实施例中，该发明涉及包含本文所披露的化合物的药物组合物，以及它们在预防和治疗Pim激酶相关疾病和病症，尤其是癌症中的用途。
• HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
  申请人：McCall John M.

  公开号：US20120277224A1

  公开（公告）日：2012-11-01

  Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

  本文披露了新的杂环化合物和组合物，以及它们作为药物治疗疾病的应用。还提供了抑制PAS激酶（PASK）在人类或动物主体中活性的方法，用于治疗疾病，如糖尿病。
• Novel heteroleptic Ru(<scp>ii</scp>) complexes: synthesis, characterization and application in dye-sensitized solar cells
  作者：Gabriele Marotta、Ch. Pavan Kumar、Maria Grazia Lobello、Francesca Cavazzini、Paolo Salvatori、Koyyada Ganesh、Mohammad Khaja Nazeeruddin、Malapaka Chandrasekharam、Filippo De Angelis

  DOI：10.1039/c4dt03633f

  日期：——

  Six new heteroleptic Ru(II) complexes (MC118, MC120–123 and MC126), of general formula Ru(L1)(L2)(NCS)2, where L1 and L2 are respectively dicarboxylated and π-conjugated functionalized (dissymmetric) bipyridine ligands, were designed, synthesized and applied as sensitizers in dye-sensitized solar cells. These complexes were characterized both experimentally and theoretically, showing promising optical

  六个新杂的Ru（II）络合物（MC118，MC120-123和MC126），通式的钌（L1）（L2）（NCS）2，其中L1和L2分别二羧基化和π共轭官能（不对称）联吡啶配位体被设计，合成并用作染料敏化太阳能电池中的敏化剂。这些配合物在实验和理论上都进行了表征，与典型的N719染料相比，显示出令人鼓舞的光学特性，具有更高的消光系数。当与液体Ⅰ工作装置，组合使用- / I 3 - 氧化还原电解质，研究过的敏化剂的功率转换效率在6.0％至8.0％之间，与在相似的制造和评估条件下测试的参比N719染料相当。