1-(苯基磺酰)-1H-吲哚-3-羰酰氯 | 99532-51-1

• 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-(苯基磺酰)-1H-吲哚-3-羰酰氯
• 英文名称: 1-phenylsulfonylindol-3-ylcarboxylic acid chloride
• 英文别名: 1-(phenylsulfonyl)-1H-indole-3-carbonyl chloride；3-(chlorocarbonyl)-1-(phenylsulfonyl)-1H-indole；3-chlorocarbonyl-1-phenylsulfonylindole；3-chlorocarbonyl-1-(phenylsulfonyl)-indole；1-(benzenesulfonyl)indole-3-carbonyl chloride
• CAS: 99532-51-1
• 化学式: C₁₅H₁₀ClNO₃S
• 分子量: 319.768
• InChiKey: RDVIVYUKRJAERC-UHFFFAOYSA-N

物化性质

• 熔点：
  144 °C
• 沸点：
  515.6±42.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• 海关编码：
  2933990090

SDS

Name:	1-(Phenylsulfonyl)-1H-indole-3-carbonyl chloride 97% Material Safety Data Sheet
Synonym:
CAS:	99532-51-1

Section 1 - Chemical Product MSDS Name:1-(Phenylsulfonyl)-1H-indole-3-carbonyl chloride 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
99532-51-1	1-(Phenylsulfonyl)-1H-indole-3-carbony	97	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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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 immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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 foam, dry chemical, or carbon dioxide.

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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:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area. Store under an inert atmosphere.

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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# 99532-51-1: 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: beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 138 - 143 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: C15H10ClNO3S
Molecular Weight: 319.77

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, exposure to moist air or water.
Incompatibilities with Other Materials:
Strong oxidizing agents, bases.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 99532-51-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(Phenylsulfonyl)-1H-indole-3-carbonyl chloride - 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: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3261
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
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.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 99532-51-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 99532-51-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 99532-51-1 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：

  1-(苯基磺酰)-1H-吲哚-3-羰酰氯 在 potassium carbonate 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 9.0h， 生成 3-氰基吲哚
  参考文献：
  名称：

  A convenient synthesis of 3-acylindoles via Friedel Crafts acylation of 1-(phenylsulfonyl)indole. A new route to pyridocarbazole-5,11-quinones and ellipticine

  摘要：

  DOI：

  10.1021/jo00350a001
• 作为产物：
  描述：

  1-(苯磺酰基)-1H-吲哚-3-羧酸 在 氯化亚砜 作用下， 反应 3.0h， 生成 1-(苯基磺酰)-1H-吲哚-3-羰酰氯
  参考文献：
  名称：

  First Synthesis of Marine Alkaloid(±)-Bengacarboline

  摘要：

  Bengacarboline 1 是一种海洋生物碱，是拓扑异构酶 II 的强效抑制剂，由吲哚-3-羧酸和色胺经九个步骤合成。

  DOI：

  10.1055/s-2003-40836

文献信息

• Straightforward Novel One-Pot Enaminone and Pyrimidine Syntheses by Coupling-Addition-Cyclocondensation Sequences
  作者：Thomas J. Müller、Alexei S. Karpov

  DOI：10.1055/s-2003-42480

  日期：——

  The coupling of acid chlorides 1 with terminal alkynes 2 using only one equivalent (!) of triethylamine under Sonogashira conditions followed by subsequent addition of primary or secondary amines 4 to the intermediate alkynones 3 represents a straightforward one-pot three component access to enaminones 5 under mild conditions and in excellent yields. Furthermore, 2,4-di- and 2,4,6-trisubstituted pyrimidines

  在 Sonogashira 条件下，酰氯 1 与末端炔烃 2 的偶联仅使用一当量 (！) 三乙胺，随后将伯胺或仲胺 4 添加到中间体炔酮 3 中，代表了一种直接的一锅三组分获得烯胺酮 5条件温和，产量高。此外，2,4-二和2,4,6-三取代的嘧啶7可以根据高度灵活的偶联-加成-环缩合序列以中等至良好的产率合成。
• A diversity oriented four-component approach to tetrahydro-β-carbolines initiated by Sonogashira coupling
  作者：Alexei S. Karpov、Frank Rominger、Thomas J. J. Müller

  DOI：10.1039/b511861a

  日期：——

  A consecutive four-component synthesis of highly-substituted tetrahydro-β-carbolines 6 can be achieved by a coupling-aminatio-aza-annulation-Pictet–Spengler (CAAPS) sequence creating five new σ-bonds and four new stereocenters in a one-pot fashion. The structures were unambiguously supported by X-ray structure analyses.

  通过耦合-氨化-氮环化-Pictet–Spengler (CAAPS) 序列，可以在一个反应体系中连续合成高度取代的四氢-β-咯啉 6，形成五个新的σ键和四个新的立体中心。这些结构得到了X射线结构分析的明确支持。
• 2-thioindoles (selenoindoles) and related disulfides (selenides) which
  申请人：Warner-Lambert

  公开号：US05464861A1

  公开（公告）日：1995-11-07

  2-Thioindoles (2-selenoindoles) and analogous 2-indolinethione (2-indolineselenone) and polysulfide (selenide) compounds, salts thereof, methods of production, intermediates in their production, pharmaceutical compositions containing said compounds, and methods for inhibiting protein kinase dependent disease in a mammal or treating aberrant cell growth in a mammal, using said compositions, are disclosed.

  本文揭示了2-硫代吲哚（2-硒代吲哚）及类似的2-吲哚硫酮（2-吲哚硒酮）和聚硫化物（硒化物）化合物，以及其盐、生产方法、生产中间体、含有该类化合物的药物组合物，以及使用这些组合物来抑制蛋白激酶依赖性疾病或治疗哺乳动物中的异常细胞生长的方法。
• First Synthesis of Marine Alkaloid(±)-Bengacarboline
  作者：Yves Langlois、Annie Pouilhès、Angèle Chiaroni

  DOI：10.1055/s-2003-40836

  日期：——

  Bengacarboline 1, a marine alkaloid, potent inhibitor of topoisomerase II, has been synthesized in nine steps from indol-3-carboxylic acid and tryptamine.

  Bengacarboline 1 是一种海洋生物碱，是拓扑异构酶 II 的强效抑制剂，由吲哚-3-羧酸和色胺经九个步骤合成。
• Synthetic Studies of Cephalandole Alkaloids and the Revised Structure of Cephalandole A
  作者：Jeffrey J. Mason、Jan Bergman、Tomasz Janosik

  DOI：10.1021/np800334j

  日期：2008.8.1

  originally proposed 2-(1 H-indol-3-yl)-4 H-3,1-benzoxazin-4-one structure of the alkaloid cephalandole A (1) led to a structural revision, and the isolated natural product has now been identified as the previously known compound 3-(1 H-indol-3-yl)-2 H-1,4-benzoxazin-2-one (7). The structural assignment was corroborated by detailed NMR studies. A short synthesis of the related natural compound cephalandole

  最初提出的2-（1 H-吲哚-3-基）-4 H-3,1-苯并恶嗪-4-酮结构的生物碱头孢烯酮A（1）的合成导致结构修订，并且分离出的天然现已将产物鉴定为先前已知的化合物3-（1 H-吲哚-3-基）-2 H-1,4-苯并恶嗪-2-酮（7）。详细的NMR研究证实了结构归属。还进行了相关天然化合物头孢烯B（2）的简短合成，证实了其结构。另外，提出了一些化学转化，包括例如相关的合成分子2-（1 H-吲哚-3-基）-3 H-喹唑啉-4-酮（9）。