2,5-二甲基-1-(4-硝基苯基)-1H-吡咯 | 5044-22-4

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2,5-二甲基-1-(4-硝基苯基)-1H-吡咯
• 中文别名: 2,5-二甲基-1-(4-硝基苯)-1H-吡咯
• 英文名称: 2,5-dimethyl-1-(4-nitrophenyl)-1H-pyrrole
• 英文别名: 1-(4-nitrophenyl)-2,5-dimethyl-1H-pyrrole；N-(4'-nitrophenyl)-2,5-dimethylpyrrole；2,5-dimethyl-1-(4-nitrophenyl)pyrrole
• CAS: 5044-22-4
• 化学式: C₁₂H₁₂N₂O₂
• mdl: MFCD00085038
• 分子量: 216.239
• InChiKey: JXJRCFOGAIXRCU-UHFFFAOYSA-N

物化性质

• 熔点：
  145-148℃
• 稳定性/保质期：

  在常温常压下，该物质保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 储存条件：
  请将药品存放在避光、阴凉干燥的地方，并密封保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2,5-Dimethyl-1-(4-nitrophenyl)pyrrole
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
2,5-Dimethyl-1-(4-nitrophenyl)pyrrole
Ingredient name:
CAS number: 5044-22-4

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C12H12N2O2
Molecular weight: 216.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用领域广泛，2,5-二甲基-1-(4-硝基苯基)-1H-吡咯可作为有机合成中间体和医药中间体，主要应用于实验室研发及医药化工生产中。

反应信息

• 作为反应物：
  描述：

  2,5-二甲基-1-(4-硝基苯基)-1H-吡咯 在 palladium on activated charcoal 氢气 作用下， 生成 4-(2,5-二甲基吡咯-1-基)苯胺
  参考文献：
  名称：

  Corelli; Massa; Stefancich, Farmaco, Edizione Scientifica, 1983, vol. 38, # 4, p. 219 - 231

  摘要：

  DOI：
• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2,5-二甲基-1-(4-硝基苯基)-1H-吡咯
  参考文献：
  名称：

  由N保护的琥珀酰亚胺方便地一锅合成多取代的吡咯

  摘要：

  由多取代的琥珀酰亚胺与Petasis试剂之间的反应形成的二烯胺产物在温和的酸性条件下进行异构化，以优异的收率（85-95％）得到多取代的吡咯。探索了这种方法的范围和局限性。

  DOI：

  10.1016/j.tetlet.2014.03.021

文献信息

• Synthesis of two distinct pyrrole moiety-containing arenes from nitroanilines using Paal–Knorr followed by an indium-mediated reaction
  作者：Byeong Hyo Kim、Seolhee Bae、Ahra Go、Hyunseung Lee、Cheoloh Gong、Byung Min Lee

  DOI：10.1039/c5ob02101d

  日期：——

  Synthesis of arenes substituted with two different substituted-pyrrole moieties was investigated.

  芳烃合成中探讨了含有两种不同取代吡咯基团的芳烃。
• Hexafluoroisopropanol as solvent and promotor in the Paal-Knorr synthesis of N-substituted diaryl pyrroles
  作者：Robert H.E. Schirmacher、Daniel Rösch、Franziska Thomas

  DOI：10.1016/j.tet.2021.131985

  日期：2021.3

  An additive-free synthesis of challenging N-substituted aryl pyrroles from the often poorly soluble corresponding 1,4-diketones by means of the Paal-Knorr pyrrole synthesis is reported, which makes use of the unique properties of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent and reaction promotor. Our procedure offers simple execution and purification as well as easy scale-up and can be applied

  据报道，通过Paal-Knorr吡咯合成方法，由通常难溶的相应1,4-二酮可无添​​加剂合成具有挑战性的N-取代的芳基吡咯，该方法利用了1,1,1,3的独特性质，3,3-六氟异丙醇（HFIP）作为溶剂和反应促进剂。我们的程序提供了简单的执行和纯化方法，以及易于放大的规模，可用于Paal-Knorr合成中，结构复杂的许多吡咯，包括中等难度到极高产率的具有挑战性的四和五取代的吡咯。HFIP也可以用作呋喃和噻吩的Paal-Knorr合成中的溶剂。然而，在吡咯的合成中，溶剂作用更为明显。
• Crystalline salicylic acid as an efficient catalyst for ultrafast Paal–Knorr pyrrole synthesis under microwave induction
  作者：Kioumars Aghapoor、Farshid Mohsenzadeh、Hossein Reza Darabi、Hani Sayahi

  DOI：10.1007/s12039-021-01891-9

  日期：2021.6

  the viability of a wide range of crystalline aromatic and aliphatic carboxylic acids as organocatalysts has been investigated for solvent-free Paal–Knorr pyrrole synthesis under microwave activation. Among these potential catalysts, crystalline salicylic acid proved to be a remarkable catalyst because its efficiency remained high even under low microwave power irradiation or a shorter reaction time

  摘要 在这项研究中，已经研究了微波活化下无溶剂的Paal-Knorr吡咯合成中各种结晶性芳族和脂肪族羧酸作为有机催化剂的可行性。在这些潜在的催化剂中，结晶水杨酸被证明是出色的催化剂，因为即使在低微波功率辐照下或模型反应的反应时间较短的情况下，其效率仍然很高。水杨酸出色的催化活性使Paal–Knorr环缩合的周转频率高达1472 h -1，这在无金属均相催化的情况下是独一无二的。这种有机催化剂的吸引人的特点是它有助于超快速的吡咯合成，并且没有金属污染的风险。 图形摘要 概要：引入了一种绿色快速的方法，该方法通过水杨酸作为催化剂（固态）与微波的组合来合成2,5-二甲基吡咯。
• Naturally occurring organic acids for organocatalytic synthesis of pyrroles via Paal–Knorr reaction
  作者：Farshid Mohsenzadeh、Hossein Reza Darabi、Mahsa Alivand、Kioumars Aghapoor、Yadollah Balavar

  DOI：10.1007/s11164-020-04260-2

  日期：2020.12

  In this study, common naturally occurring organic acids, namely oxalic, malonic, succinic, tartaric and citric acid (as safe, inexpensive, and biodegradable organocatalysts), have been employed for Paal–Knorr pyrrole synthesis. The organocatalyzed reaction proved to be effective in ethanol at 60 °C. However, the reaction rate is mainly dominated by the nature and position of functional groups on the

  在这项研究中，常见的天然有机酸，即草酸、丙二酸、琥珀酸、酒石酸和柠檬酸（作为安全、廉价和可生物降解的有机催化剂）已被用于 Paal-Knorr 吡咯合成。证明有机催化反应在 60 °C 下在乙醇中是有效的。然而，反应速率主要取决于官能团在底物芳环上的性质和位置。这种无金属工艺可以容忍一系列官能团，应该被视为制药行业的一项资产，因为在吡咯支架的合成过程中不会发生金属污染。
• Microwave-induced calcium(II) chloride-catalyzed Paal–Knorr pyrrole synthesis: a safe, expeditious, and sustainable protocol
  作者：Kioumars Aghapoor、Farshid Mohsenzadeh、Hossein Reza Darabi、Saeed Rastgar

  DOI：10.1007/s11164-018-3355-7

  日期：2018.7

  alkaline-earth (Ca, Mg, Sr, Ba) chlorides, calcium(II) chloride was found to be a cost-effective Lewis acid catalyst for solvent-free synthesis of pyrroles from primary aromatic and aliphatic amines under open-vessel focused microwave irradiation. The salient features of this environmentally benign method are high to quantitative conversion, short reaction time, safe and clean reaction profile, possibility of

  摘要 在各种碱金属（Na，K）和碱土金属（Ca，Mg，Sr，Ba）氯化物中，氯化钙（II）被认为是一种经济有效的路易斯酸催化剂，用于从伯芳族化合物和芳族化合物中无溶剂合成吡咯。在开放容器聚焦微波辐射下的脂肪胺。这种对环境无害的方法的显着特征是具有高的定量转化率，较短的反应时间，安全和清洁的反应曲线，可放大至数克数量级的可能性以及使用低成本，可广泛获得的无毒催化剂。 图形概要