4-溴-1-(三异丙基硅基)-1H-吲哚 | 412048-44-3

• 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: 4-溴-1-(三异丙基硅基)-1H-吲哚
• 中文别名: 4-溴-1-三异丙基甲硅烷基-1H-吲哚
• 英文名称: 4-Bromo-1-(tri-isopropylsilyl)-1H-indole
• 英文别名: 4-bromo-N-triisopropylsilylindole；4-bromo-1-TIPS-indole；N-TIPS-4-bromoindole；4-bromo-triisopropylsilanyl-1H-indole；4-bromo-1-triisopropylsilanyl-1H-indole；4-bromo-1-(triisopropylsilyl)-1H-indole；(4-bromoindol-1-yl)-tri(propan-2-yl)silane
• CAS: 412048-44-3
• 化学式: C₁₇H₂₆BrNSi
• 分子量: 352.39
• InChiKey: ZXHMUQVMGJYGAV-UHFFFAOYSA-N

物化性质

• 熔点：
  62 °C
• 沸点：
  339.8±24.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

SDS

Name:	4-Bromo-1-(triisopropylsilyl)-1H-indole Material Safety Data Sheet
Synonym:	None known
CAS:	412048-44-3

Section 1 - Chemical Product MSDS Name:4-Bromo-1-(triisopropylsilyl)-1H-indole Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
412048-44-3	4-Bromo-1-(triisopropylsilyl)-1h-indol	97+%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
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# 412048-44-3: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Off white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C17H26BrNSi
Molecular Weight: 352.39

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents, acid chlorides, reducing agents, strong acids.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide, hydrogen bromide, bromine.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 412048-44-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Bromo-1-(triisopropylsilyl)-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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 23 Do not inhale gas/fumes/vapour/spray.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 412048-44-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 412048-44-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 412048-44-3 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：

  4-溴-1-(三异丙基硅基)-1H-吲哚 在 正丁基锂 、 重水 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以21 %的产率得到(4-2H)-1H-indole
  参考文献：
  名称：

  使用进化光酶对芳烃进行区域选择性自由基烷基化

  摘要：

  取代芳烃普遍存在于具有药用功能的分子中，这使得它们的合成成为设计合成路线时的关键考虑因素。区域选择性 C-H 官能化反应对于制备烷基化芳烃很有吸引力；然而，现有方法的选择性有限，并且主要受基底的电子特性控制。在这里，我们展示了一种生物催化剂控制的方法，用于富电子和缺电子杂芳烃的区域选择性烷基化。从非选择性“烯”还原酶 (ERED) (GluER-T36A) 开始，我们进化出一种选择性烷基化吲哚 C4 位的变体，这是使用现有技术难以捉摸的位置。整个进化系列的机制研究表明，蛋白质活性位点的变化改变了负责自由基形成的电荷转移（CT）复合物的电子特征。这导致了 CT 复合体中具有显着程度的基态 CT 的变体。对 C2 选择性 ERED 的机制研究表明，GluER-T36A 的进化有助于抑制竞争机制途径。针对 C8 选择性喹啉烷基化进行了额外的蛋白质工程活动。这项研究强调了使用酶进行区域选择性自由基

  DOI：

  10.1021/jacs.3c03607
• 作为产物：
  描述：

  4-溴吲哚 、 三异丙基氯硅烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 4-溴-1-(三异丙基硅基)-1H-吲哚
  参考文献：
  名称：

  新型二氢喹啉-4（1H）-酮衍生物作为新型微管蛋白聚合抑制剂的设计、合成和生物学评价

  摘要：

  设计、合成了一系列靶向秋水仙碱结合位点的新型二氢喹啉-4（1H）-酮衍生物，并评价作为抗癌剂。最有效的化合物 6t 对四种癌细胞系显示出显着的抗增殖活性，IC50 值在 0.003-0.024 μM 之间，微管蛋白聚合抑制活性 （IC50 = 3.06 μM）。进一步的机制研究显示，化合物 6t 可诱导 K562 细胞凋亡并在 G2/M 期停滞。同时，6t 在体外显著抑制 MDA-MB-231 细胞的迁移和侵袭，并破坏人脐静脉内皮细胞 （HUVECs） 的血管生成。此外，化合物 6t 抑制 H22 同种异体移植肿瘤模型中的肿瘤生长，肿瘤生长抑制 （TGI） 率为 63.3 % （静脉注射，20 mg/kg 每天），无明显毒性。总的来说，这些结果表明化合物 6t 是一种新型微管蛋白聚合抑制剂，在体外和体内具有强大的抗癌特性。

  DOI：

  10.1016/j.ejmech.2023.115881

文献信息

• 4-piperazinylindole derivatives with 5-HT6 receptor affinity
  申请人：——

  公开号：US20030045527A1

  公开（公告）日：2003-03-06

  This invention relates to compounds which have generally 5-HT6 receptor affinity and which are represented by Formula I: 1 wherein R 3 is SO 2 —Ar, Ar is aryl or heteroaryl; and R 1 , R 2 , R 4 and R 5 are as defined herein; or individual isomers, racemic or non-racemic mixtures of isomers, or pharmaceutically acceptable salts or solvates thereof. The invention further relates to pharmaceutical compositions containing such compounds, methods for their use as therapeutic agents, and methods of preparation thereof.

  这项发明涉及一类通常具有5-HT6受体亲和力的化合物，其由以下式I表示： 其中R3为SO2—Ar，Ar为芳基或杂环芳基；R1、R2、R4和R5如本文所定义；或其各个异构体、外消旋或非外消旋异构体混合物，或其药用可接受盐或溶剂化合物。该发明还涉及含有这类化合物的药物组合物，以及它们作为治疗剂的使用方法和其制备方法。
• New indazole and indolone derivatives and their use pharmaceuticals
  申请人：Allerton Norfor Charlotte Moira

  公开号：US20050267096A1

  公开（公告）日：2005-12-01

  The present invention provides for compounds of formula (I), which are a class of dopamine agonists, more particularly a class of agonists that are selective for D3 over D2. These compounds are useful for the treatment and/or prevention of sexual dysfunction, for example female sexual dysfunction (FSD), in particular female sexual arousal disorder (FSAD), hypoactive sexual desire disorder (HSDD; lack of interest in sex), female orgasmic disorder (FOD; inability to achieve orgasm); and male sexual dysfunction, in particular male erectile dysfunction (MED). Male sexual dysfunction as referred to herein is meant to include ejaculatory disorders such as premature ejaculation, anorgasmia (inability to achieve orgasm) or desire disorders such as hypoactive sexual desire disorder (HSDD; lack of interest in sex). These compounds are also useful in treating neuropsychiatric disorders and neurodegenerative disorders.

  本发明提供了一类多巴胺激动剂的化合物，具体来说是一类选择性作用于D3而非D2的激动剂。这些化合物可用于治疗和/或预防性功能障碍，例如女性性功能障碍（FSD），特别是女性性唤醒障碍（FSAD），性欲不振障碍（HSDD；对性欲缺乏兴趣），女性性高潮障碍（FOD；无法达到高潮）；以及男性性功能障碍，特别是男性勃起功能障碍（MED）。本文提到的男性性功能障碍包括射精障碍，如早泄，无法达到高潮的无性感（无法达到高潮）或性欲障碍，如性欲不振（HSDD；对性欲缺乏兴趣）。这些化合物还可用于治疗神经精神障碍和神经退行性疾病。
• Novel compounds, their use and preparation
  申请人：——

  公开号：US20020165251A1

  公开（公告）日：2002-11-07

  The invention provides 2, 3-, 4- or 5-substituted-N1-(arylsulfonyl)indole and (heteroaryl)indole compounds of the general formula (I): 1 in which Ar, R 2 , R 3 , R 4 and R 5 are as defined in the specification. The compounds bind to the 5-HT 6 receptor and are useful for the treatment and prophylaxis of disorders mediated by the 5-HT 6 receptor, such as obesity and CNS disorders.

  这项发明提供了一般式(I)中的2,3-,4-或5-取代-N1-(芳基磺酰基)吲哚和(杂环基)吲哚化合物： 其中Ar，R2，R3，R4和R5如规范中定义。这些化合物与5-HT6受体结合，并可用于治疗和预防由5-HT6受体介导的疾病，如肥胖和中枢神经系统疾病。
• Synthesis of Polyarylated Methanes through Cross-Coupling of Tricarbonylchromium-Activated Benzyllithiums
  作者：Genette I. McGrew、Jesada Temaismithi、Patrick J. Carroll、Patrick J. Walsh

  DOI：10.1002/anie.201000957

  日期：——

  Coordinated to the tricarbonylchromium fragment, a typically unstable benzylic organolithium can participate directly in cross‐coupling reactions with aryl bromides to form polyarylated methane derivatives (see scheme). Cr(CO)3 assistance leads to reactivity with a variety of coordinated substrates and—given multiple benzylic sites—can effect up to six coupling events per arene.

  支持基团：与三羰基铬片段配位，典型不稳定的苄基有机锂可以直接参与与芳基溴的交叉偶联反应，形成多芳基化甲烷衍生物（参见方案）。Cr(CO) 3的协助导致与各种配位底物的反应性，并且在给定多个苄基位点的情况下，可以影响每个芳烃多达六个偶联事件。
• Practical Catalytic Asymmetric Synthesis of Diaryl-, Aryl Heteroaryl-, and Diheteroarylmethanols
  作者：Luca Salvi、Jeung Gon Kim、Patrick J. Walsh

  DOI：10.1021/ja9046747

  日期：2009.9.2

  successfully added to aldehydes and heteroaryl aldehydes with enantioselectivities between 81-99%. These are the first examples of catalytic and highly enantioselective syntheses of diheteroarylmethanols. In a similar fashion, ferrocenyl bromide was used to generate FcZnEt and the ferrocenyl group added to benzaldehyde and heteroaromatic aldehydes to form ferrocene-based ligand precursors in 86-95%

  对映体富集的二芳基、芳基杂芳基和二杂芳基甲醇表现出重要的生物和医学特性。介绍了从容易获得的芳基溴开始，一锅催化不对称合成这些化合物。因此，溴化锂与市售芳基溴化物和n-BuLi进行交换，然后与ZnCl(2)进行盐复分解以生成ArZnCl。添加第二当量的正丁基锂以形成混合有机锌 ArZnBu。在对映体富集的氨基醇基催化剂存在下，ArZnBu 与醛加成，基本上得到外消旋的二芳基甲醇。低对映选择性归因于 LiCl 促进的背景反应。为了抑制这种背景反应，在添加醛之前引入螯合二胺 TEEDA（四乙基乙二胺）。在这些条件下，获得了对映体富集的二芳基甲醇，其 ee 大于 90%。烯醛的芳基化生成具有 81-90% ee 的烯丙醇。然而，当应用于杂芳基溴时，该过程并不成功，这归因于杂芳基锂在盐复分解条件下的分解。为了避免这个问题，用EtZnCl进行复分解，这使得盐复分解可以在低温下进行。所得的 EtZn(Ar(杂))