1-叔丁氧羰基-5-氯吲哚 | 129822-48-6

• 物质功能分类: 医药中间体 - 吲哚类化合物
• 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-叔丁氧羰基-5-氯吲哚
• 中文别名: 1-BOC-5-氯吲哚；1-(叔丁氧基羰基)-5-氯吲哚
• 英文名称: tert-butyl 5-chloro-1H-indole-1-carboxylate
• 英文别名: 1-(tert-butoxycarbonyl)-5-chloroindole；tert-butyl 5-chloroindole-1-carboxylate
• CAS: 129822-48-6
• 化学式: C₁₃H₁₄ClNO₂
• 分子量: 251.713
• InChiKey: GBBULIKZPZSTLA-UHFFFAOYSA-N

物化性质

• 熔点：
  45-50 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  S36/37
• 危险类别码：
  R25
• 海关编码：
  2933990090
• WGK Germany：
  3
• 危险标志：
  GHS06
• 危险品运输编号：
  UN 2811 6.1/PG 3
• 危险性描述：
  H301,H317,H413
• 危险性防范说明：
  P280,P301 + P310
• 包装等级：
  III
• 危险类别：
  6.1
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-BOC-5-Chloroindole
Synonyms: tert-Butyl 5-chloro-1H-indole-1-carboxylate

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H301: Toxic if swallowed
H317: May cause an allergic skin reaction
H413: May cause long lasting harmful effects to aquatic life
P280: Wear protective gloves/protective clothing/eye protection/face protection
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician

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Section 3. Composition/information on ingredients.
Ingredient name: 1-BOC-5-Chloroindole
CAS number: 129822-48-6

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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
This product should be handled only by, or under the close supervision of, those properly qualified
Handling:
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: C13H14ClNO2
Molecular weight: 251.7

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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 chloride.

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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
UN Number: UN2811 Class: 6.1 Packing group: III
Proper shipping name: TOXIC SOLIDS, ORGANIC, N.O.S. (1-BOC-5-Chloroindole)

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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-叔丁氧羰基-5-氯吲哚 在 2,2,2-三氟乙醇 作用下， 反应 1.0h， 以98%的产率得到5-氯吲哚
  参考文献：
  名称：

  Deprotection of N-BOC compounds

  摘要：

  具有叔丁氧羰基保护的含氮有机化合物可以通过在氟代醇溶液中加热来有效去保护。

  公开号：

  EP2070899A1
• 作为产物：
  描述：

  (4-chloro-2-methyl-phenyl)-carbamic acid tert-butyl ester 在 盐酸 、 仲丁基锂 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 1-叔丁氧羰基-5-氯吲哚
  参考文献：
  名称：

  Preparation of Indoles and Oxindoles fromN-(tert-Butoxycarbonyl)-2-alkylanilines

  摘要：

  使用双锂化的N-(叔丁氧羰基)苯胺1与二甲基甲酰胺或二氧化碳反应，可得到中间体3和5，它们分别容易转化为N-(叔丁氧羰基)吲哚4和氧化吲哚（吲哚-2(3H)-酮，7）。双锂化的1与N-甲氧基-N-甲基酰胺缩合得到酮9，这些酮在三氟乙酸处理下环化，根据反应时间的不同，形成2-取代的1-(叔丁氧羰基)吲哚10或2-取代的吲哚11。这一通用方法已被应用于高效合成1,2-烷基桥联吲哚12、1,3,4,5-四氢苯[c,d]吲哚（16）、2a,3,4,5-四氢苯[c,d]吲哚-2(1H)-酮（18）以及1-(叔丁氧羰基)-1H-吡咯并[2,3-b]吡啶（21）。

  DOI：

  10.1055/s-1991-26597

文献信息

• Reductive Electrophotocatalysis: Merging Electricity and Light To Achieve Extreme Reduction Potentials
  作者：Hyunwoo Kim、Hyungjun Kim、Tristan H. Lambert、Song Lin

  DOI：10.1021/jacs.9b10678

  日期：2020.2.5

  strategy that harnesses the power of light and electricity to generate an excited radical anion with a reducing potential of -3.2 V vs SCE, which can be used to activate substrates with very high reduction potentials (Ered ≈ -1.9 to -2.9 V). The resultant aryl radicals can be engaged in various synthetically useful transformations to furnish arylboronate, arylstannane, and biaryl products.

  我们描述了一种新的电光催化策略，该策略利用光和电的力量产生还原电位为 -3.2 V vs SCE 的激发自由基阴离子，可用于激活具有非常高还原电位（Ered ≈ -1.9 至 - 2.9 伏）。所得芳基可参与各种合成有用的转化，以提供芳基硼酸酯、芳基锡烷和联芳基产物。
• Suzuki–Miyaura Cross-Coupling of Potassium Dioxolanylethyltrifluoroborate and Aryl/Heteroaryl Chlorides
  作者：Nicolas Fleury-Brégeot、Daniel Oehlrich、Frederik Rombouts、Gary A. Molander

  DOI：10.1021/ol400320q

  日期：2013.4.5

  A robust and efficient protocol for the introduction of the dioxolanylethyl moiety onto various aryl and heteroaryl halides has been developed, providing cross-coupling yields up to 93%. Copper-catalyzed borylation of 2-(2-bromoethyl)-1,3-dioxolane with bis(pinacolato)diboron followed by treatment with potassium bifluoride provides the key organotrifluoroborate reagent.

  已经开发出一种将二氧戊环基乙基部分引入各种芳基和杂芳基卤化物的稳健而有效的方案，提供高达 93% 的交叉偶联产率。铜催化的 2-(2-溴乙基)-1,3-二氧戊环与双(频哪醇)二硼硼化，然后用氟化氢钾处理，提供了关键的有机三氟硼酸盐试剂。
• Photoinduced Miyaura Borylation by a Rare-Earth-Metal Photoreductant: The Hexachlorocerate(III) Anion
  作者：Yusen Qiao、Qiaomu Yang、Eric J. Schelter

  DOI：10.1002/anie.201804022

  日期：2018.8.20

  photoreductant, a Miyaura borylation, has been achieved. This simple, scalable, and novel borylation method that makes use of the hexachlorocerate(III) anion ([CeIIICl6]3−, derived from CeCl3) has a broad substrate scope and functional‐group tolerance and can be conducted at room temperature. Combined with Suzuki–Miyaura cross‐coupling, the method is applicable to the synthesis of various biaryl products, including

  稀土金属光还原剂Miyaura硼酸盐化反应实现了第一个光诱导的碳（sp 2）-杂原子键形成反应。这种简单，可扩展且新颖的硼酸化方法利用六氯cerate（III）阴离子（[Ce III Cl 6 ] 3−，源自CeCl 3），具有广泛的底物范围和官能团耐受性，可以在室温下进行温度。结合Suzuki-Miyaura交叉偶联，该方法适用于各种联芳基产物的合成，包括通过使用芳基氯化物底物。
• Nickel-Catalyzed Dearomative Arylboration of Indoles: Regioselective Synthesis of C2- and C3-Borylated Indolines
  作者：Grace L. Trammel、Rositha Kuniyil、Phillip F. Crook、Peng Liu、M. Kevin Brown

  DOI：10.1021/jacs.1c05902

  日期：2021.10.13

  the C2- or C3-positions. Synthetically useful C2- and C3-borylated indolines can be accessed through a simple change in N-protecting group in high regio- and diastereoselectivities (up to >40:1 rr and >40:1 dr) from readily available starting materials. Additionally, the origin of regioselectivity was explored experimentally and computationally to uncover the remarkable interplay between carbonyl orientation

  吲哚脱芳构化是获取二氢吲哚的重要策略：二氢吲哚是存在于多种天然产物和生物活性分子中的基序。本文提出了一种过渡金属催化吲哚区域选择性脱芳香芳基硼化反应生成多种二氢吲哚的方法。该方法通过在 C2-或 C3-位置上缺乏激活或导向基团的底物上的迁移插入途径实现简单吲哚的分子间脱芳构化。合成有用的 C2- 和 C3- 硼酸化二氢吲哚可以通过简单改变N-保护基团以高区域选择性和非对映选择性（高达 >40:1 rr 和 >40:1 dr）从容易获得的起始材料获得。此外，通过实验和计算探索了区域选择性的起源，以揭示吲哚上N保护基团的羰基取向、C2-C3 π 键的电子和空间之间的显着相互作用。该方法首次实现了 (−)-azamedicarpin 的对映选择性合成。
• Insights into the Catalytic Activity of [Pd(NHC)(cin)Cl] (NHC=IPr, IPr^Cl , IPr^Br ) Complexes in the Suzuki-Miyaura Reaction
  作者：Frédéric Izquierdo、Caroline Zinser、Yury Minenkov、David B. Cordes、Alexandra M. Z. Slawin、Luigi Cavallo、Fady Nahra、Catherine S. J. Cazin、Steven P. Nolan

  DOI：10.1002/cctc.201701279

  日期：2018.2.7

  palladium N‐heterocyclic carbene complexes and their activity in the Suzuki–Miyaura reaction were investigated. Two [Pd(NHC)(cin)Cl] complexes bearing IPrCl and IPrBr ligands (IPr=1,3‐bis(2,6‐diisopropyl‐phenyl)imidazol‐2‐ylidene; cin=cinnamyl) were synthesized. After determining the electronic and steric properties of these ligands, their properties were compared to those of [Pd(IPr) (cin)Cl]. The three

  研究了C 4,5卤代化对钯N-杂环卡宾配合物及其在Suzuki-Miyaura反应中的活性的影响。两种带有IPr Cl和IPr Br的[Pd（NHC）（cin）Cl]配合物合成了配体（IPr = 1,3-双（2,6-二异丙基-苯基）咪唑-2-亚基; cin =肉桂基）。在确定这些配体的电子和空间特性后，将它们的特性与[Pd（IPr）（cin）Cl]进行比较。通过使用DFT计算研究了三种钯配合物，以描绘它们在导致推定的12电子活性催化剂的活化步骤中的行为。通过实验，研究了它们在低催化剂负载下在Suzuki-Miyaura反应中的催化活性，该反应涉及广泛的偶联伙伴（30个条目）。