5-碘吲哚 | 16066-91-4

• 物质功能分类: 医药中间体 - 原料药中间体
• 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-碘吲哚
• 中文别名: 5-碘代吲哚；5-碘-1H-吲哚
• 英文名称: 5-iodo-1H-indole
• 英文别名: 5-iodoindole；5-Jod-indol；5-Iod-indol
• CAS: 16066-91-4
• 化学式: C₈H₆IN
• mdl: MFCD00220065
• 分子量: 243.047
• InChiKey: TVQLYTUWUQMGMP-UHFFFAOYSA-N

物化性质

• 熔点：
  101-104 °C (lit.)
• 沸点：
  341.7±15.0 °C(Predicted)
• 密度：
  1.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  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：
  存于室温环境中，并避免光线直射。

SDS

Name:	5-Iodo-1H-indole 95+% Material Safety Data Sheet
Synonym:
CAS:	16066-91-4

Section 1 - Chemical Product MSDS Name:5-Iodo-1H-indole 95+% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16066-91-4	5-Iodo-1H-indole	95+%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause 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.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 16066-91-4: 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: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 95 - 96 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:
Specific Gravity/Density:
Molecular Formula: C8H6IN
Molecular Weight: 243

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen iodide, iodine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 16066-91-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-Iodo-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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 16066-91-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16066-91-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16066-91-4 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

制备方法与用途

简介

5-碘吲哚是一种吲哚衍生物。吲哚类化合物是自然界中存在最多的杂环化合物，在医药、农药、染料及香料等精细化学品中有广泛的应用，是一类重要的有机化工原料和产品。其中，大部分苯环上含有取代基的吲哚类化合物都具有较好的生物活性。

用途

5-碘吲哚作为一种重要的有机中间体，在合成医药、染料以及香料等方面有着重要的应用价值。

反应信息

• 作为反应物：
  描述：

  5-碘吲哚 在 caesium carbonate 、 硫脲 、 copper(II) oxide 作用下， 以 二甲基亚砜 为溶剂， 以75%的产率得到5-(1H-indol-5-ylthio)-1H-indole
  参考文献：
  名称：

  氧化铜纳米颗粒通过芳基卤化物与硫脲的级联反应催化芳基硫醚的合成

  摘要：

  通过芳族卤化物与廉价和可商购的硫脲的交叉偶联，开发出可循环的氧化铜纳米颗粒催化简单而高效的合成对称芳基硫醚的方法，该硫脲被用作有效的硫代用品。通过与各种取代的芳基卤化物的级联反应，产生所需的芳基硫醚，本发明的硫脲的交叉偶联方案具有避免臭味的硫醇的附加优点。

  DOI：

  10.1016/j.tetlet.2011.03.070
• 作为产物：
  描述：

  6-碘吲哚啉 在 salcomine 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以71%的产率得到5-碘吲哚
  参考文献：
  名称：

  Somei, Masanori; Saida, Yoshihiro; Funamoto, Tetsuo, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 8, p. 3146 - 3154

  摘要：

  DOI：

文献信息

• Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds
  申请人：Abbott Laboratories

  公开号：US20040116518A1

  公开（公告）日：2004-06-17

  The present invention relates to novel cinnamide compounds that are useful for treating inflammatory and immune diseases and cerebral vasospasm, to pharmaceutical compositions containing these compounds, and to methods of inhibiting inflammation or suppressing immune response in a mammal.

  本发明涉及新型肉桂酰胺化合物，用于治疗炎症和免疫性疾病以及脑血管痉挛，以及含有这些化合物的药物组合物，以及在哺乳动物中抑制炎症或抑制免疫反应的方法。
• The copper(<scp>ii</scp>)-catalyzed and oxidant-promoted regioselective C-2 difluoromethylation of indoles and pyrroles
  作者：Dong Zhang、Zheng Fang、Jinlin Cai、Chengkou Liu、Wei He、Jindian Duan、Ning Qin、Zhao Yang、Kai Guo

  DOI：10.1039/d0cc03345f

  日期：——

  highly selective C-2 difluoromethylation of indole derivatives was developed by using sodium difluoromethylsulfinate (HCF2SO2Na) as the source of difluoromethyl groups and a Cu(II) complex as the catalyst. Various substrates were well tolerated in this transformation and the desired products were obtained in moderate to good yields. Moreover, the late-stage C-2 difluoromethylation of bioactive molecules

  通过使用二氟甲基亚磺酸钠（HCF 2 SO 2 Na）作为二氟甲基的来源和Cu（II）络合物作为催化剂，开发了一种新颖且高效的吲哚衍生物高选择性C-2二氟甲基化方法。在这种转化中，各种底物都具有良好的耐受性，并且以中等至良好的产率获得了所需的产物。此外，以高收率实现了含有吲哚环的生物活性分子的后期C-2二氟甲基化。通常，该反应具有出色的官能团相容性，广泛的底物范围和出色的C-2选择性。
• Cu-mediated C2-dehydrogenative homocoupling of indoles via C–H activation assisted by a removable N-pyrimidyl group
  作者：Jun Le、Yadong Gao、Yousong Ding、Chao Jiang

  DOI：10.1016/j.tetlet.2016.03.027

  日期：2016.4

  Cu-mediated regioselective, dehydrogenative homocoupling of indoles was developed using AgNO3 as the additive. The easily installed and removed N-pyrimidyl group exerted complete C2 regiocontrol via C–H activation. A series of indole substrates underwent cross-dehydrogenative-homocoupling. This work developed an effective approach for the synthesis of 2,2′-biindole core of a number of chemicals fundamentally

  使用AgNO 3作为添加剂，开发了铜介导的吲哚区域选择性，脱氢均偶联。易于安装和除去的N-嘧啶基通过CH活化可完全控制C2区域。一系列吲哚底物经历了交叉脱氢-均偶联。这项工作开发了一种有效的方法，用于合成对材料和药物化学至关重要的许多化学物质的2,2'-联吲哚核。
• 一种合成2,2’-二聚吲哚类化合物的方法
  申请人：南京理工大学

  公开号：CN105622585B

  公开（公告）日：2018-04-03

  本发明公开了一种合成2,2’‑二聚吲哚类化合物的方法。首先以吲哚类化合物为原料，在氢化钠碱性条件下，通过吲哚或取代吲哚与2‑氯嘧啶反应生成1‑(嘧啶基‑2‑基)‑1H‑吲哚类化合物，向吲哚类化合物中引入嘧啶导向基团，之后1‑(嘧啶基‑2‑基)‑1H‑吲哚类化合物在醋酸铜、硝酸银和甲苯溶剂的参与下进行自身二聚反应，最终合成2,2’‑二聚吲哚类化合物。本发明运用直接碳氢活化的反应方法，减少了反应步骤，提高了反应经济性，在温和的条件下，高效合成了目标产物2,2’‑二聚吲哚类化合物，2,2’‑二聚吲哚类化合物脱保护反应后可离去嘧啶基团，生成2,2’‑二聚吲哚，此结构单元具有广泛的生物活性和广阔的应用前景。
• Generation of Organozinc Reagents from Arylsulfonium Salts Using a Nickel Catalyst and Zinc Dust
  作者：Kodai Yamada、Tomoyuki Yanagi、Hideki Yorimitsu

  DOI：10.1021/acs.orglett.0c03782

  日期：2020.12.18

  powder under nickel catalysis via the selective cleavage of the sp2-hybridized carbon–sulfur bond to produce salt-free arylzinc triflates under mild conditions. This zincation displays superb chemoselectivity and thus represents a protocol that is complementary or orthogonal to existing methods. The generated arylzinc reagents show both high reactivity and chemoselectivity in palladium-catalyzed and copper-mediated

  现成的芳基二甲基tri三氟甲磺酸盐在镍催化下通过选择性裂解sp 2-杂化碳-硫键与锌粉反应，在温和条件下生成无盐的芳基锌三氟甲磺酸盐。这种镀锌显示出极好的化学选择性，因此代表了与现有方法互补或正交的方案。生成的芳基锌试剂在钯催化和铜介导的交叉偶联反应中均显示出高反应活性和化学选择性。