1-(3-硝基苯基)-1H-吡咯 | 4310-42-3

• 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-硝基苯基)-1H-吡咯
• 中文别名: 1-(3-硝基苯基)吡咯
• 英文名称: 1-(3-nitrophenyl)-1H-pyrrole
• 英文别名: 1-(3-nitrophenyl)pyrrole
• CAS: 4310-42-3
• 化学式: C₁₀H₈N₂O₂
• mdl: MFCD02665276
• 分子量: 188.186
• InChiKey: GTWSUEQDVMZTRP-UHFFFAOYSA-N

物化性质

• 熔点：
  72 °C
• 沸点：
  319.8±25.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 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：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090

SDS

Name:	1-(3-Nitrophenyl)-1h-pyrrole 97% Material Safety Data Sheet
Synonym:
CAS:	4310-42-3

Section 1 - Chemical Product MSDS Name:1-(3-Nitrophenyl)-1h-pyrrole 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4310-42-3	1-(3-Nitrophenyl)-1H-pyrrole	97%	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# 4310-42-3: 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: 72 - 74 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: C10H8N2O2
Molecular Weight: 188.19

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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.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4310-42-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(3-Nitrophenyl)-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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 4310-42-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 4310-42-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4310-42-3 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-硝基苯基)-1H-吡咯 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 二苯醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.5h， 生成 1-乙基-1,4-二氢-4-氧代-7-(1-吡咯基)喹啉-3-羧酸乙酯
  参考文献：
  名称：

  Corelli; Massa; Stefancich, Farmaco, Edizione Scientifica, 1984, vol. 39, # 2, p. 95 - 109

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-二硝基苯 在 盐酸 、 indium 作用下， 以 水 为溶剂， 反应 1.25h， 生成 1-(3-硝基苯基)-1H-吡咯
  参考文献：
  名称：

  Novel Approach for the Synthesis ofN-Substituted Pyrroles Starting Directly from Nitro Compounds in Water

  摘要：

  A novel approach for a facile high-yielding synthesis of N-substituted pyrroles has been discovered by the treatment of nitroarenes with 2,5-dimethoxytetrahydrofuran using indium in dilute aqueous HCl at room temperature.

  DOI：

  10.1080/00397911.2010.526748

文献信息

• Palladium‐Catalyzed Methylation of Nitroarenes with Methanol
  作者：Lin Wang、Helfried Neumann、Matthias Beller

  DOI：10.1002/anie.201814146

  日期：2019.4.8

  procedure for the synthesis of N‐methyl‐arylamines directly from nitroarenes using methanol as green methylating agent was developed. The key to success is the use of a specific catalyst system consisting of palladium acetate and the ligand 1‐[2,6‐bis(isopropyl)phenyl]‐2‐[tert‐butyl(2‐pyridinyl)phosphino]‐1H‐Imidazole (L1). The generality of this protocol is demonstrated in the synthesis of more than 20

  开发了使用甲醇作为绿色甲基化剂直接从硝基芳烃合成N-甲基-芳基胺的方法。成功的关键是使用由乙酸钯和配位体的1- [2,6-双（异丙基）苯基] -2- [叔-丁基（2-吡啶基）膦基] -1的特定催化剂体系的ħ -咪唑（L1）。在相对温和的条件下合成20多种N-甲基-芳基胺证明了该方案的普遍性。将这种新颖的方法与使用相同催化剂的后续偶联工艺相结合，可以使芳香族硝基化合物有效地分散为包括药物分子在内的各种胺类。
• Synthesis of 2-Arylbenzothiazol-5-amines from N,N-Dialkyl-3-nitroanilines
  作者：Tung T. Nguyen、Nam T. S. Phan、Hang T. Pham、Tuan H. Ho、Duy Q. Do、Kim L. H. Nguyen

  DOI：10.1055/s-0040-1706470

  日期：2020.11

  We report a simple method for coupling of N,N-dialkyl-3-nitroarenes, elemental sulfur, and activated sp3 C–H bonds in 2-methylazaarenes or arylacetic acids to afford derivatives of 2-arylbenzothiazol-5-amines. Only DABCO base was required, and many heterocycles such as imidazoles, oxazoles, quinolines, and thiophenes were compatible with the reaction conditions. Our approach offers a simple route to useful substituted thiazol-5-amines from commercially available nitroarenes.

  我们报道了一种简单的方法，用于耦合N，N-二烷基-3-硝基芳烃，元素硫和2-甲基氮杂芳烃或芳乙酸中的活化sp3 C-H键，以提供2-芳基苯并噻唑-5-胺衍生物。仅需要DABCO碱，并且许多杂环如咪唑，噁唑，喹啉和噻吩都与反应条件兼容。我们的方法提供了一种从商业上可用的硝基芳烃合成有用的取代噻唑-5-胺的简单途径。

• 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。
• Sulphonic acid functionalized porphyrin anchored with a <i>meso</i>-substituted triazolium ionic liquid moiety: a heterogeneous photo-catalyst for metal/base free C–C cross-coupling and C–N/C–H activation using aryl chloride under visible light irradiation
  作者：Karan Bhansali、Subodh Raut、Shital Barange、Pundlik Bhagat

  DOI：10.1039/d0nj03637d

  日期：——

  is an efficient photocatalyst for the Heck, Sonogashira, Buchwald, Ullmann/Fittig coupling and C–H activation of phenols with different aryl chlorides in the absence of a base/noble metal, using 5 W LED (yellow) light under ambient conditions. The photocatalyst with low band gap (1.55 eV) comprising conjugation, favors coupling reaction of unactivated aryl chlorides, by easy excitation of electrons

  我们报告了一种简单的合成磺酸官能化卟啉的方法，该方法与内消旋的三唑鎓离子液体部分（SAFPTILM）固定，可在可见光下使用芳基氯进行金属/碱自由的C-C交叉偶联和C-N / C-H活化光照射。酸强度已经基于哈米特指示剂进行了测量。SAFPTILM光催化剂包含18个π共轭电子体系，内消旋有生色团取代基位置可以在可见光的照射下的光催化过程中提供快速的电子传导通道。研究发现，使用5 W LED（黄色）光时，SAFPTILM是在没有碱金属/贵金属的情况下，用于Heck，Sonogashira，Buchwald，Ullmann / Fittig偶联和苯酚与不同的芳基氯化物的C–H活化的有效光催化剂。在环境条件下。具有低带隙（1.55 eV）的光催化剂具有共轭作用，通过易于激发电子并转移至基于共轭苯并咪唑鎓的苯二胺载体上，有利于未活化的芳基氯的偶联反应，从而延迟了光致电子-空穴对的重组。
• Ligands for Copper-Catalyzed C−N Bond Forming Reactions with 1 Mol% CuBr as Catalyst
  作者：Kai Yang、Yatao Qiu、Zheng Li、Zhaoyang Wang、Sheng Jiang

  DOI：10.1021/jo1026035

  日期：2011.5.6

  Several new ligands were designed to promote copper-catalyzed Ullman C−N coupling reactions. In this group, 8-hydroxyquinolin-N-oxide was found to serve as a superior ligand for CuBr-catalyzed coupling reactions of aryl iodides, bromides, and chlorides with aliphatic amines and N-heterocycles under a low catalyst loading (1% [Cu] mol). Reactions with the inexpensive catalytic system display a high

  设计了几种新的配体来促进铜催化的Ullman C-N偶联反应。在该组中，8羟基喹啉Ñ氧化物被发现作为的CuBr催化的低催化剂负载下偶合芳基碘化物，溴化物，并用脂族胺和N-杂环氯化物的反应（1％优异的配体[铜] mol）。使用廉价的催化体系进行的反应显示出较高的官能团耐受性和出色的化学选择性。（1）

表征谱图