1-(4-硝基苯基)-2-吡咯烷酮 | 13691-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(4-硝基苯基)-2-吡咯烷酮
• 中文别名: 1-(4-硝基苯基)吡咯烷-2-酮
• 英文名称: 1-(4-nitrophenyl)pyrrolidin-2-one
• CAS: 13691-26-4
• 化学式: C₁₀H₁₀N₂O₃
• mdl: MFCD00138492
• 分子量: 206.201
• InChiKey: YYYMDBUHBOEDTC-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130 °C
• 沸点：
  345.04°C (rough estimate)
• 密度：
  1.2815 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S24/25
• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Name:	1-(4-Nitrophenyl)-2-Pyrrolidinone 99+%(GC) Material Safety Data Sheet
Synonym:	None Known
CAS:	13691-26-4

Section 1 - Chemical Product MSDS Name:1-(4-Nitrophenyl)-2-Pyrrolidinone 99+%(GC) Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13691-26-4	1-(4-Nitrophenyl)-2-Pyrrolidinone	99+%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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:

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate 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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use only in a chemical fume hood.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 13691-26-4: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Crystalline powder
Color: brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 128 - 130 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H10N2O3
Molecular Weight: 206.20

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13691-26-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(4-Nitrophenyl)-2-Pyrrolidinone - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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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# 13691-26-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13691-26-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13691-26-4 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

反应信息

• 作为反应物：
  描述：

  1-(4-硝基苯基)-2-吡咯烷酮 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以97%的产率得到1-(4'-硝基苯基)吡咯烷-2-硫酮
  参考文献：
  名称：

  Synthesis of ω-Aminodithioesters

  摘要：

  通过与三酸烷基酯反应，再与硫化氢发生硫解作用，从硫代内酰胺中获得了Ï-氨基二硫酯衍生物。δ-、δ-和µ-硫代内酰胺的开环需要在 N1 位（对硝基苯基或苯甲酰基）上存在一个取电子基团。就 β-thionolactam 而言，C3 位上的 CF2 基团可提供活化作用。

  DOI：

  10.1055/s-2006-942452
• 作为产物：
  描述：

  1-苯基-2-吡咯烷酮 在 硫酸 、 硝酸 作用下， 反应 0.25h， 以90%的产率得到1-(4-硝基苯基)-2-吡咯烷酮
  参考文献：
  名称：

  对硝基blebbistatin，无细胞毒性和光稳定的肌球蛋白II抑制剂

  摘要：

  Blebbistatin是特征最强的肌球蛋白II抑制剂，通常用于研究各种肌球蛋白II同工型的生物学作用。尽管其广受欢迎，但由于其蓝光敏感性极大地阻碍了抑菌素的使用，从而导致该分子的光毒性和光转化。此外，即使在没有照射的情况下，blebbistatin仍具有严重的细胞毒性副作用，这可能容易导致对实验结果的误解，因为细胞毒性衍生的表型可能归因于肌球蛋白II功能的抑制。在这里，我们报告了blebbistatin的光稳定，C15硝基衍生物具有不受影响的肌球蛋白II抑制特性的合成以及体外和体内的表征。重要的是，对如细胞和动物试验所显示，硝基硝化抑素既无光毒性也无细胞毒性；因此，在体外和体内，它都可以作为无限制和完全替代blebbistatin的药物。

  DOI：

  10.1002/anie.201403540

文献信息

• Highly selective reduction of nitroarenes by iron(0) nanoparticles in water
  作者：Raju Dey、Nirmalya Mukherjee、Sabir Ahammed、Brindaban C. Ranu

  DOI：10.1039/c2cc30999h

  日期：——

  Highly selective reduction of nitroarenes has been achieved using iron metal nanoparticles in water at room temperature. A wide spectrum of reducible functionalities remained inert under the reaction conditions. During the reaction a change in shape of Fe nanoparticles was observed.

  在室温下的水相环境中，利用铁金属纳米颗粒实现了硝基芳烃的高度选择性还原。在反应条件下，广泛的还原性官能团保持惰性。反应过程中观察到了铁纳米颗粒形状的变化。
• Ring-Expanding Reaction of Cyclopropyl Amides with Triphenylphosphine and Carbon Tetrahalide
  作者：Yong-Hua Yang、Min Shi

  DOI：10.1021/jo0516988

  日期：2005.10.1

  prepared in situ in the presence of 2 equiv of PPh3 and 1 equiv of CX4, and the ring-expanding products (N-substituted pyrrolidin-2-ones) were obtained in good yields. The reaction mechanism was investigated on the basis of oxygen-18 tracer experiment.

  我们成功地通过在2当量的PPh 3和1当量的CX 4和扩环产物（N-取代的吡咯烷-2-酮）存在下原位制备的相应的酰亚胺基卤化物活化了环丙基酰胺（单活化的环丙烷）。以高收率获得。在氧18示踪实验的基础上研究了反应机理。
• Cyclization of <i>N</i> -arylcyclopropanecarboxamides into <i>N</i> -arylpyrrolidin-2-ones under electron ionization and in the condensed phase
  作者：A. T. Lebedev、D. M. Mazur、A. I. Kudelin、A. N. Fedotov、I. P. Gloriozov、Yu. A. Ustynyuk、V. B. Artaev

  DOI：10.1002/rcm.7717

  日期：2016.11.30

  calculations the principal mechanism of decomposition of the molecular ions of N-arylcyclopropanecarboxamides involves their direct fragmentation without any rearrangements. An alternative mechanism is responsible for the isomerisation of a small portion of the higher energy molecular ions into the corresponding N-arylpyrrolidin-2-one ions. Copyright © 2016 John Wiley & Sons, Ltd.

  理性分析质谱法是预测溶液中有机化合物行为的出色方法。质谱仪离子源内部气相中有机化合物的行为可以定义其固有性质，从而避免了分子间相互作用，抗衡离子和溶剂效应的影响。方法通过缩合相合成法从相应的N-芳基环丙烷甲酰胺中获得芳基吡咯烷-2-酮。电子电离（EI）通过高分辨率的飞行时间质谱和量子化学计算进行精确的质量测量，用于了解N-芳基环丙烷甲酰胺和N-芳基吡咯烷-2-酮在其中的分子自由基阳离子的行为。质谱仪的离子源。分子的几何形状，过渡态，使用DFT-PBE计算完全优化了中间体。结果提出了异构体N-芳基环丙烷甲酰胺和N-芳基吡咯烷丁-2-酮的碎片化方案，离子结构和可能的一级异构化机理。基于N-芳基环丙烷甲酰胺的碎片化模式，原始的M +•离子异构化为N-芳基吡咯烷丁-2-酮的M +•离子仅是一个较小的过程。相反，在布朗斯台德酸的存在下，该环化反应在缩合相中易于进行。结论基于实验数据和量子化学计算，N
• Iridium(<scp>iii</scp>)-catalyzed regioselective direct arylation of sp² C–H bonds with diaryliodonium salts
  作者：Pan Gao、Li Liu、Zhuangzhi Shi、Yu Yuan

  DOI：10.1039/c6ob01145d

  日期：——

  A regioselective direct arylation of arenes and olefins at the ortho position is reported. The key to the high selectivity is the appropriate choice of diaryliodonium salts as the arylating reagent in the presence of a cationic iridium(III) catalyst. The coordination of the metal with an oxygen atom or a nitrogen atom and subsequent C–H activation allows for direct arylation with coupling partners

  据报道在邻位的芳烃和烯烃的区域选择性直接芳基化。到高选择性的关键是二芳基碘盐作为阳离子铱（存在下芳基化试剂的合适的选择III）催化剂。金属与氧原子或氮原子的配位以及随后的C–H活化可实现与偶联配偶体的直接芳基化。该反应在温和的反应条件下进行，并且对包括许多卤化物官能团在内的各种官能团具有较高的耐受性。
• The rhodium-catalysed synthesis of pyrrolidinone-substituted (trialkylsilyloxy)acrylic esters
  作者：Daniel L. Priebbenow、Carsten Bolm

  DOI：10.1039/c3ra41527a

  日期：——

  A method for the preparation of novel pyrrolidine substituted (trialkylsilyloxy)acrylic esters has been developed. The protocol involves a rhodium-catalysed O-insertion/rearrangement reaction between N-functionalised 2-pyrrolidinones and α-silyl α-diazoacetates to form the corresponding acrylic esters in moderate to high yields.

  已经开发了一种制备新型吡咯烷取代的（三烷基甲硅烷基氧基）丙烯酸酯的方法。该方案涉及在N-官能化的2-吡咯烷酮和α-甲硅烷基α-二重氮乙酸酯之间的铑催化的O-插入/重排反应，以中等至高产率形成相应的丙烯酸酯。