1-[(4-氯苯基)磺酰基]-1H-吡咯 | 16851-83-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-[(4-氯苯基)磺酰基]-1H-吡咯
• 英文名称: 1-((4-chlorophenyl)sulfonyl)-1H-pyrrole
• 英文别名: 1-[(4-chlorophenyl)sulfonyl]-1H-pyrrole；1-(4-chlorophenyl)sulfonylpyrrole
• CAS: 16851-83-5
• 化学式: C₁₀H₈ClNO₂S
• mdl: MFCD00067753
• 分子量: 241.698
• InChiKey: ACNNPPGRQRFTSO-UHFFFAOYSA-N

物化性质

• 熔点：
  116-117 °C
• 沸点：
  393.6±44.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090

SDS

Name:	1-[(4-Chlorophenyl)sulfonyl]-1h-pyrrole 97% Material Safety Data Sheet
Synonym:
CAS:	16851-83-5

Section 1 - Chemical Product MSDS Name:1-[(4-Chlorophenyl)sulfonyl]-1h-pyrrole 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16851-83-5	1-[(4-Chlorophenyl)sulfonyl]-1H-pyrrol	97%	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# 16851-83-5: 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 - grey
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 116 - 118 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: C10H8ClNO2S
Molecular Weight: 242

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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:
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# 16851-83-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-[(4-Chlorophenyl)sulfonyl]-1H-pyrrole - 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: 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# 16851-83-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16851-83-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16851-83-5 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-[(4-氯苯基)磺酰基]-1H-吡咯 在 sodium tetrahydroborate 、 三氯化铝 作用下， 以 四氢呋喃 为溶剂， 生成 [1-(4-Chloro-benzenesulfonyl)-1H-pyrrol-3-yl]-(2,4-dichloro-phenyl)-methanol
  参考文献：
  名称：

  1-Arylsulfonyl-3-(α-hydroxybenzyl)-1H-pyrroles, a novel class of anti-HIV-1 reverse transcriptase inhibitors

  摘要：

  Various 1-arylsulfonyl-3-(alpha-hydroxybenzyl)-1H-pyrroles were prepared by Friedel-Crafts reaction of 1-aryisulfonyl-1H-pyrroles with aroylchlorides in the presence of aluminum trichloride, followed by reduction of the ketones to the required carbinols. Title compounds were identified as a novel class of nonnucleoside HIV-1 reverse transcriptase inhibitors characterized by the presence of a diarylcarbinol moiety, a chemical feature that strictly correlates with the anti-HTV-1 activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00340-5
• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 4-氯苯磺酰胺 在 对甲苯磺酸一水合物 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以88%的产率得到1-[(4-氯苯基)磺酰基]-1H-吡咯
  参考文献：
  名称：

  通过磺酰基吡咯进行初级磺酰胺官能化：从不同的角度观察 N-Ts 键

  摘要：

  磺胺类药物在药物分子中很普遍，然而，通过 S-N 键裂解功能化磺胺类药物的方法很少。基于对 N-Ts 脱保护的重新评估，我们开发了磺酰吡咯作为磺酰胺功能化的关键。磺酰基吡咯参与可以通过化学、电化学或光化学途径进行的各种转化。

  DOI：

  10.1002/chem.202102748

文献信息

• A Facile Synthesis of N-Substituted Pyrroles
  作者：Y. Fang、D. Leysen、H. C. J. Ottenheijm

  DOI：10.1080/00397919508015431

  日期：1995.6

  Abstract Phosphorous pentoxide is the catalyst of choice for the facile conversion of primary amines, aromatic amines, sulfonamides and primary amides into the corresponding N-substituted pyrroles from 2,5-dimethoxytetrahydrofuran.

  摘要 五氧化二磷是将伯胺、芳香胺、磺酰胺和伯酰胺从 2,5-二甲氧基四氢呋喃轻松转化为相应的 N-取代吡咯的首选催化剂。
• Iron-Catalyzed Inexpensive and Practical Synthesis of N-Substituted Pyrroles in Water
  作者：Najmedin Azizi、Alireza Khajeh-Amiri、Hossein Ghafuri、Mohammad Bolourtchian、Mohammad Saidi

  DOI：10.1055/s-0029-1217799

  日期：2009.9

  An operationally simple, practical, and economical protocol for iron(III) chloride catalyzed Paal-Knorr pyrrole synthesis in water in good to excellent yields has been developed. Several N-substituted pyrroles are readily prepared from the reaction of 2,5-dimethoxytetrahydrofuran and aryl/alkyl, sulfonyl and acyl amines under very mild reaction conditions

  一种操作简便、实用且经济的实验方案已被开发，用于在水相中以铁(III)氯化物为催化剂进行Paal-Knorr吡咯合成，产率良好至优异。在非常温和的反应条件下，多个N-取代吡咯可以方便地通过2,5-二甲氧基四氢呋喃与芳基/烷基、磺酰基和酰基胺的反应来制备。
• Synthesis of N-Sulfonyl- and N-Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction
  作者：Weiqiang Chen、Yin-Lin Zhang、Hui-Jing Li、Xiang Nan、Ying Liu、Yan-Chao Wu

  DOI：10.1055/s-0039-1690002

  日期：2019.10

  N-acylpyrroles were synthesized via olefin ring-closing metathesis of diallylamines and in situ oxidative aromatization in the presence of the ruthenium Grubbs catalyst and a suitable copper catalyst. In the presence of Cu(OTf)2 and CuBr2, the reaction afforded N-sulfonyl- and N-acylpyrroles, respectively, in one pot. Under an oxygen atmosphere, the reaction went smoothly without the need of hydroperoxide

  抽象的 N-磺酰基-和N-酰基吡咯是通过二烯丙基胺的烯烃闭环易位和在钌Grubbs催化剂和合适的铜催化剂的存在下原位氧化芳构化而合成的。在Cu（OTf）2和CuBr 2的存在下，反应在一锅中分别得到N-磺酰基-和N-酰基吡咯。在氧气气氛下，不需要氢过氧化物氧化剂即可使反应顺利进行。该方案具有许多优点，例如使用无害氧化剂和易于获得的起始原料，在一个锅中操作，并显示出广泛的底物范围。 N-磺酰基-和N-酰基吡咯是通过二烯丙基胺的烯烃闭环易位和在钌Grubbs催化剂和合适的铜催化剂的存在下原位氧化芳构化而合成的。在Cu（OTf）2和CuBr 2的存在下，反应在一锅中分别得到N-磺酰基-和N-酰基吡咯。在氧气气氛下，不需要氢过氧化物氧化剂即可使反应顺利进行。该方案具有许多优点，例如使用无害氧化剂和易于获得的起始原料，在一个锅中操作，并显示出广泛的底物范围。
• Triflic acid controlled successive annelation of aromatic sulfonamides: an efficient one-pot synthesis of N-sulfonyl pyrroles, indoles and carbazoles
  作者：Mohammed Abid、Liliana Teixeira、Béla Török

  DOI：10.1016/j.tetlet.2007.04.021

  日期：2007.6

  A novel one-pot synthesis of N-substituted heterocycles via successive cyclization/annelation starting from primary sulfonamides is described. This process leads directly to N-sulfonyl pyrroles, indoles and carbazoles. The selection of appropriate reactant/triflic acid ratio successfully controls the formation of the desired product.

  描述了一种从伯磺酰胺开始通过连续环化/退火来合成 N-取代杂环的新型一锅法。该过程直接生成N-磺酰基吡咯、吲哚和咔唑。选择适当的反应物/三氟甲磺酸比率成功地控制了所需产物的形成。
• AN EFFICIENT AND RAPID SYNTHESIS OF N-SUBSTITUTED PYRROLES BY MICROWAVE ASSISTED SOLID ACID CATALYSIS
  作者：Mohammed Abid、Shainaz M. Landge、Béla Török

  DOI：10.1080/00304940609356444

  日期：2006.10

  total synthesis of these compounds .' Accordingly, extended efforts have been made toward the synthesis of wide range of pyrrole derivatives. Most of these methods involve various cyclocondensations reactions resulting in 254or polysubstituted pyrroles.2 However, the environmentally benign synthesis of N-monosubstituted pyrroles is still a challenge. The commonly used traditional P205 catalysis has disadvantages

  F'yrroles 代表一类重要的杂环化合物，在许多具有生物活性的天然产物中作为结构基序出现，并在这些化合物的全合成中充当构件。因此，已经为合成广泛的吡咯衍生物做出了更大的努力。这些方法中的大多数涉及各种环缩合反应，产生 254 或多取代吡咯。2 然而，N-单取代吡咯的环境友好合成仍然是一个挑战。常用的传统P205催化反应时间长、收率低、处理困难等缺点？我们的目标是开发一种新的现代方法，既能提供高产量，又能满足最近的环境标准和安全问题。在过去的几十年中，大量出版物表明，固体酸催化 4 和微波辐射已成为有机合成中的重要工具。K-10 蒙脱石是有机合成中最著名和应用最广泛的固体酸之一。由于其强酸性、显着的表面积和高稳定性，它是酸和双功能催化的首选催化剂：继续我们在固体酸催化合成有机化合物方面的努力，henein 我们报告了一种新型的、单锅、通用和使用蒙脱石 K10 和微波辐射快速合成 N 取代的吡咯。对于初步研究，我们选择了苯胺与