4-(2,5-二甲基吡咯-1-基)苯胺 | 60176-19-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 4-(2,5-二甲基吡咯-1-基)苯胺
• 英文名称: 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzenamine
• 英文别名: 4-(2,5-dimethyl-1H-pyrrol-1-yl)aniline；4-(2,5-dimethylpyrrol-1-yl)aniline
• CAS: 60176-19-4
• 化学式: C₁₂H₁₄N₂
• mdl: MFCD01125287
• 分子量: 186.257
• InChiKey: OGCFQHCSVLMKFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  31
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(2,5-Dimethyl-pyrrol-1-yl)-phenylamine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 4-(2,5-Dimethyl-pyrrol-1-yl)-phenylamine
CAS number: 60176-19-4

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
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.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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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.
Store in closed vessels.
Storage:

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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
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C12H14N2
Molecular weight: 186.3

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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

反应信息

• 作为反应物：
  描述：

  4-(2,5-二甲基吡咯-1-基)苯胺 在 sodium hydroxide 、 potassium carbonate 作用下， 以 二苯醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.92h， 生成 1-ethyl-1,4-dihydro-4-oxo-6-(2,5-dimethylpyrrol-1-yl)quinoline-3-carboxylic acid
  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：

  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：

文献信息

• One-pot Tandem Reactions for Direct Conversion of Thiols and Disulfides to Sulfonic Esters, Alcohols to Bis(indolyl)methanes and Synthesis of Pyrroles Catalyzed by N-Chloro Reagents
  作者：Hojat Veisi、Meral Ataee、Leila Fatolahi、Shahram Lotfi

  DOI：10.2174/1570178611310020008

  日期：2013.4.1

  convenient synthesis of sulfonic esters from thiols and disulfides has been described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with Chloramin-T, tetra-butylammonium chloride (t-Bu4NCl) and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of bis(indolyl)methanes from alcohols

  已经描述了由硫醇和二硫化物方便地合成磺酸酯的方法。由硫醇原位制备磺酰氯的方法是用氯丁宁-T，氯化四丁基铵（t-Bu 4 NCl）和水氧化。然后使磺酰氯在同一反应容器中与苯酚衍生物反应。同样，在温和的条件下，使用TCCA / KBr / wet-SiO 2和N-取代的吡咯通过TCCA / KBr / wet-SiO 2从醇中轻松合成双（吲哚基）甲烷已在温和条件下以优异的收率完成。
• Direct Synthesis of Pyrroles via Heterogeneous Catalytic Condensation of Anilines with Bioderived Furans
  作者：Lei Tao、Zi-Jian Wang、Tian-Hao Yan、Yong-Mei Liu、He-Yong He、Yong Cao

  DOI：10.1021/acscatal.6b02953

  日期：2017.2.3

  Given the wide applications of pyrroles in agriculture, pharmaceuticals, and supramolecular and materials chemistry, a mild and eco-friendly route to produce functionalized pyrroles from bioderived feedstocks is highly desirable. Described herein is a mild and convenient synthesis of pyrroles via direct condensation of an equimolar amount of structurally diverse anilines with biobased furans catalyzed

  鉴于吡咯在农业，制药，超分子和材料化学中的广泛应用，非常需要一种温和且环保的途径，以生物衍生的原料生产功能化的吡咯。本文描述了通过简单和有效的固体酸H形式的沸石Y催化剂催化的等摩尔量的结构上不同的苯胺与生物基呋喃的直接缩合，温和且方便地合成吡咯。该方案可耐受多种官能团，并提供了一种通用且通用的方法，用于按比例放大合成各种N-取代的吡咯化合物。最重要的是，可以通过这种方法获得最近被证实对治愈结肠癌非常有效的生物活性吡咯衍生药物吡虫鎓。
• Modified Paal-Knorr Synthesis of Novel and Known Pyrroles Using Tungstate Sulfuric Acid as a Recyclable Catalyst
  作者：Bahador Karami、Masih Jamshidi、Saeed Khodabakhshi

  DOI：10.2174/1570178611310010005

  日期：2013.2.1

  Tungstate sulfuric acid (TSA) as a solid acid catalyst has been synthesized and used in Paal–Knorr synthesis of some novel and known pyrroles under solvent-free conditions. Catalyst loadings can be as low as 1 mol % to give high yields of the corresponding pyrroles at 60 °C. To make the catalyst, sodium tungstic reacted with chlorosulfonic acid in nhexane.

  钨酸硫酸（TSA）作为固体酸催化剂已被合成，并在无溶剂条件下用于Paal-Knorr合成一些新颖的已知吡咯。催化剂负载量可低至1 mol％，以在60°C时获得高产率的相应吡咯。为了制备催化剂，钨酸钠与氯磺酸在正己烷中反应。
• Green and Rapid Strategy for Synthesis of Novel and Known Pyrroles by the Use of Molybdate Sulfuric Acid
  作者：Bahador Karami、Saeed Khodabakhshi、Masih Jamshidi

  DOI：10.1002/jccs.201300012

  日期：2013.9

  Molybdate sulfuric acid as a highly efficient catalyst has been employed for the modified Paal–Knorr synthesis of some novel and known pyrroles under solvent‐free conditions. Catalyst loads as low as 1 mol% could be used leading to high yields of pure pyrrole derivatives at an oil bath temperature of 60 °C. This method has advantages such as the use of very low amounts of a recyclable catalyst, avoidance

  钼酸硫酸作为高效催化剂已用于无溶剂条件下某些新型和已知吡咯的Paal-Knorr改性合成。可以使用低至1 mol％的催化剂负载量，从而在60°C的油浴温度下获得高产率的纯吡咯衍生物。该方法具有诸如使用非常少量的可再循环催化剂，避免有机溶剂和高产物收率的优点。
• Greener Paal-Knorr Pyrrole Synthesis by Mechanical Activation
  作者：Liudvikas Akelis、Jolanta Rousseau、Robertas Juskenas、Jelena Dodonova、Cyril Rousseau、Stéphane Menuel、Dominique Prevost、Sigitas Tumkevičius、Eric Monflier、Frédéric Hapiot

  DOI：10.1002/ejoc.201501223

  日期：2016.1

  A straightforward and solventless synthesis of pyrroles was developed by using mechanochemical activation and a biosourced organic acid as the catalyst. Relative to traditional Paal–Knorr methodologies, various N-substituted pyrroles were obtained in very short reaction times. By reaction with unreactive diketones, desymmetrized aliphatic and aromatic compounds were also synthesized.

  通过使用机械化学活化和生物来源的有机酸作为催化剂，开发了一种简单且无溶剂的吡咯合成方法。相对于传统的 Paal-Knorr 方法，可以在很短的反应时间内获得各种 N 取代的吡咯。通过与不活泼的二酮反应，还合成了去对称的脂肪族和芳香族化合物。