1-(3-溴苯基)-1H-吡咯 | 107302-22-7

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-(3-溴苯基)-1H-吡咯
• 中文别名: 1-(3-溴苯)-1H-吡咯；1-(3-溴苯基)-1H吡咯
• 英文名称: 1-(3-bromophenyl)-1H-pyrrole
• 英文别名: 1-(3-bromophenyl)pyrrole
• CAS: 107302-22-7
• 化学式: C₁₀H₈BrN
• mdl: MFCD02665243
• 分子量: 222.084
• InChiKey: LEUXOIBRUWVBGM-UHFFFAOYSA-N

物化性质

• 熔点：
  63 °C
• 沸点：
  294.9±23.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险等级：
  IRRITANT
• 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
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Name:	1-(3-Bromophenyl)-1h-pyrrole 95+% Material Safety Data Sheet
Synonym:
CAS:	107302-22-7

Section 1 - Chemical Product MSDS Name:1-(3-Bromophenyl)-1h-pyrrole 95+% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
107302-22-7	1-(3-Bromophenyl)-1H-pyrrole	95+%	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# 107302-22-7: 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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 63 - 64 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: C10H8BrN
Molecular Weight: 222.08

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 107302-22-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(3-Bromophenyl)-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# 107302-22-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 107302-22-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 107302-22-7 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-(3-溴苯基)-1H-吡咯 在 4-二甲氨基吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 水 、 potassium acetate 、 potassium carbonate 、 N,N'-羰基二咪唑 、 sodium hydroxide 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 N-(9H-purin-6-yl)-3'-(1H-pyrrol-1-yl)-[1,1'-biphenyl]-4-carboxamide
  参考文献：
  名称：

  使用基于片段的方法鉴定胞质5'-核苷酸酶II的非竞争性抑制剂

  摘要：

  我们使用了基于片段药物设计（FBDD）和计算机方法的组合方法来设计潜在的细胞溶质5'-核苷酸酶II（cN-II）抑制剂，该抑制剂被公认为血液学癌症的重要治疗靶标。小化合物的两个亚组（包括腺嘌呤和联芳基部分）被确定为cN-II结合剂，并考虑了通过分子对接引导的片段增长策略。五种化合物在体外强烈抑制5'-核苷酸酶活性，最有力的抑制剂被定性为非竞争性抑制剂。癌细胞系中的生物学评估显示了与所选抗癌药物的协同作用。使用X射线晶体学的结构研究导致了对两种衍生物的新结合位点的鉴定，以及表明重要结构域交换的新晶体形式的鉴定。总之，本文开发的策略允许鉴定新的抗cN-II的原始非竞争性抑制剂，这些抑制剂以与已知的抗肿瘤剂协同作用的方式起作用。

  DOI：

  10.1021/acs.jmedchem.5b01616
• 作为产物：
  描述：

  在 劳森试剂 作用下， 以 甲苯 为溶剂， 生成 1-(3-溴苯基)-1H-吡咯
  参考文献：
  名称：

  作为乙酰胆碱酯酶保留丁酰胆碱酯酶抑制剂的吡咯衍生物的发现

  摘要：

  受（杂）芳基环在胆碱酯酶抑制剂中的关键作用和吡咯环在新药发现中的启发，我们合成了 19 种吡咯衍生物并研究了它们的胆碱酯酶抑制活性。因此，具有 1,3-二芳基吡咯骨架的化合物 3o、3p 和 3s 对 BChE 的选择性高于 AChE，具有最佳 IC50值为 1.71 ± 0.087 µM，与多奈哌齐相当。进一步预测了这些结构的药物潜力，并证明化合物3o和3p很好地满足Lipinsky的五个规则。结合抑制动力学研究和分子对接结果，我们得出结论，化合物 3p 以混合竞争模式抑制 BChE。该研究证明了1,3-二芳基吡咯骨架作为一种选择性BChE抑制剂的潜力。

  DOI：

  10.3389/fphar.2022.1043397

文献信息

• [DE] 2-HETEROARYLCARBONSÄUREAMIDE<br/>[EN] 2-HETEROARYL CARBOXAMIDES<br/>[FR] 2-HETEROARYLCARBOXAMIDES
  申请人：BAYER HEALTHCARE AG

  公开号：WO2003104227A1

  公开（公告）日：2003-12-18

  Die Erfindung betrifft neue 2-Heteroarylcarbonsäureamide und ihre Verwendung zur Herstellung von Arzneimitteln zur Behandlung und/oder Prophylaxe von Krankheiten und zur Verbesserung der Wahrnehmung, Konzentrationsleistung, Lernleistung und/oder Gedächtnisleistung. (I): in welcher R1 1-Aza-bicyclo [2.2.2]oct-3-yl, welches gegebenenfalls über das Sticktoffätom mit einem Rest ausgewählt aus der Gruppe C1-C4-Alkyl, Benzyl und Oxy substituiert ist, A Sauerstoff oder Schwefel, der Ring B Benzo oder Pyrido, die jeweils gegebenenfalls durch Reste aus der Reihe Halogen, Cyano, Formyl, Trifluormethyl, Trifluormethoxy, Nitro, Amino, C1-C6-Alkyl und C1-C6-Alkoxy substituiert sind, E C≡C, Aryl und Heteroaryl, wobei Aryl und Heteroaryl durch Reste aus der Reihe Halogen, Cyano, Trifluormethyl, Trifluormethyl, Trifluormethoxy, Nitro, Amino, C1-C6-Alkoxy und C1-C6-Alkyl substituiert sein Können, bedeuten, sowie die Solvate, Salze oder Solvate der Salze dieser Verbindungen.

  这项发明涉及新的2-杂环芳基羧酰胺及其用于制备用于治疗和/或预防疾病以及改善感知、注意力、学习和/或记忆能力的药物的用途。其中，R1为1-Aza-bicyclo[2.2.2]oct-3-yl，可能通过氮原子与来自C1-C4-烷基、苄基和氧的基团中的一种取代，A为氧或硫，环B为苯并或吡啶，并且可以通过来自卤素、氰基、甲酰基、三氟甲基、三氟甲氧基、硝基、氨基、C1-C6-烷基和C1-C6-烷氧基的基团取代，E为C≡C、芳基和杂环芳基，其中芳基和杂环芳基可以通过来自卤素、氰基、三氟甲基、三氟甲基、三氟甲氧基、硝基、氨基、C1-C6-烷氧基和C1-C6-烷基的基团取代，以及这些化合物的溶剂化合物、盐或盐的溶剂化合物。
• l-(+)-Tartaric acid and choline chloride based deep eutectic solvent: An efficient and reusable medium for synthesis of N-substituted pyrroles via Clauson-Kaas reaction
  作者：Ping Wang、Fei-Ping Ma、Zhan-Hui Zhang

  DOI：10.1016/j.molliq.2014.07.015

  日期：2014.10

  l-(+)-Tartaric acid–choline chloride based deep eutectic solvent has been found to be an effective promoted medium for Clauson-Kaas reaction of aromatic amines and 2,5-dimethoxytetrahydrofuran. Structurally diverse N-substituted pyrroles were obtained in high to excellent yields under mild conditions. The deep eutectic solvent is inexpensive, non-toxic, reusable and biodegradable.

  已经发现，基于1 -（+）-酒石酸-氯化胆碱的低共熔溶剂是促进芳香胺和2,5-二甲氧基四氢呋喃的Clauson-Kaas反应的有效促进介质。在温和条件下以高产率至优异产率获得结构多样的N-取代的吡咯。该深共晶溶剂便宜，无毒，可重复使用且可生物降解。
• Friedel-Crafts trifluoromethylthiolation of electron-rich (hetero)arenes with trifluoromethylthio-saccharin in 2,2,2-trifluoroethanol (TFE)
  作者：Shiyao Lu、Wenbo Chen、Qilong Shen

  DOI：10.1016/j.cclet.2019.07.060

  日期：2019.12

  Abstract A promoter-free Friedel-Crafts trifluoromethylthiolation of electron-rich arenes and heteroarenes with N-trifluoromethylthiosaccharin 5 using 2,2,2-trifluoroethanol (TFE) as the solvent was described. The reactions were conducted at 40 °C and a variety of common functional groups were compatible.

  摘要描述了以2,2,2-三氟乙醇（TFE）为溶剂，用N-三氟甲基硫代糖精5对富电子芳烃和杂芳烃进行无助剂的Friedel-Crafts三氟甲基硫醇化反应。反应在40°C下进行，并且各种常见的官能团均相容。
• Efficient copper-catalyzed N-arylations of nitrogen-containing heterocycles and aliphatic amines in water
  作者：Xufeng Li、Daoshan Yang、Yuyang Jiang、Hua Fu

  DOI：10.1039/c002172e

  日期：——

  A simple and efficient copper-catalyzed method has been developed for N-arylations of nitrogen-containing heterocycles and aliphatic amines in water. The protocol uses (1E,2E)-oxalaldehyde dioxime (OADO) as the ligand, and water as the solvent, and shows good tolerance towards various functional groups.

  一种简单高效的铜催化方法已被开发用于氮含杂环和脂肪胺在水中的N-芳基化反应。该协议使用(1E,2E)-草醛二肟（OADO）作为配体，水作为溶剂，并对多种官能团表现出良好的耐受性。
• Solvent and ligand effects on selective mono- and dilithiation of 1-(chlorophenyl)pyrroles and 1-(methoxyphenyl)pyrroles †
  作者：Katalin Fogassy、Krisztina Kovács、György M. Keserű、László Tőke、Ferenc Faigl

  DOI：10.1039/b100008j

  日期：——

  methods for site-selective lithiation of 1-(chlorophenyl)pyrroles and 1-(methoxyphenyl)pyrroles are described. Mono- or dilithiations are governed by change of both the temperature and the solvent from tetrahydrofuran to diethyl ether. Regioselectivities could be influenced by the quality of the metallating agent. Thus, 1-(4-chlorophenyl)pyrrole was dilithiated with activated butyllithium at 0 °C to

  描述了用于1-（氯苯基）吡咯和1-（甲氧基苯基）吡咯的位点选择性锂化的新方法。单晶或双晶由温度和温度的变化控制。溶剂 从 四氢呋喃 到 乙醚。区域选择性可能受金属化剂质量的影响。因此，1-（4-氯苯基）吡咯 将其在0℃下用活化的丁基锂二锂化，以提供吡咯并苯并氮杂卓合成中的有价值的中间体。

表征谱图