1-(3-氨基苯基)-2,5-二甲基吡咯 | 247225-33-8

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 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-氨基苯基)-2,5-二甲基吡咯
• 中文别名: 3-(2,5-二甲基-1H-吡咯-1-基)苯胺
• 英文名称: 3-(2,5-dimethyl-1H-pyrrol-1-yl)aniline
• 英文别名: 1-(3-aminophenyl)-2,5-dimethylpyrrole；3-(2,5-dimethylpyrrol-1-yl)aniline
• CAS: 247225-33-8
• 化学式: C₁₂H₁₄N₂
• mdl: MFCD01125302
• 分子量: 186.257
• InChiKey: PFZUTDHSWLXVSZ-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
• WGK Germany：
  3
• 危险标志：
  GHS05,GHS07
• 危险性描述：
  H302,H318
• 危险性防范说明：
  P280,P305 + P351 + P338
• 储存条件：
  | 室温 |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(2,5-Dimethylpyrrol-1-yl)aniline
Synonyms: N-(3-Aminophenyl)-2,5-dimethylpyrrole

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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: 3-(2,5-Dimethylpyrrol-1-yl)aniline
CAS number: 247225-33-8

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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, refrigerated.
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：

  1-(3-氨基苯基)-2,5-二甲基吡咯 在 sodium acetate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 氯苯 为溶剂， 反应 33.58h， 生成 3-(2-chloro-5-(methylthio)phenyl)-1-(3-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl)-1-methylguanidine
  参考文献：
  名称：

  新型胺胍衍生物的合成，放射性标记和评价，作为N-甲基-d-天冬氨酸受体离子通道的潜在正电子发射断层显像示踪剂

  摘要：

  的Ñ -甲基- d -天冬氨酸受体（NMDAR）参与许多神经障碍和精神障碍，包括阿尔茨海默氏病和精神分裂症。这项研究的目的是开发一种正电子发射断层扫描（PET）配体，以评估NMDAR离子通道在体内的生物利用度。合成了一系列的三-N-取代的二芳基胍，并在大鼠前脑膜级分中评估了它们对NMDAR离子通道的体外结合亲和力。化合物21，23和26与任一碳-11或氟-18并放射性标记体外在Wistar大鼠中进行了生物分布和代谢物研究。生物分布研究表明，尤其是在额叶前额皮层中摄取较高，而在小脑中摄取最低。但是，用MK-801进行预处理不会降低对放射性标记配体的吸收。另外，所有三个配体均显示出快速的新陈代谢。

  DOI：

  10.1016/j.ejmech.2016.04.022
• 作为产物：
  描述：

  1-(3-硝基苯基)-2,5-二甲基吡咯 在 铁粉 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 0.3h， 以92%的产率得到1-(3-氨基苯基)-2,5-二甲基吡咯
  参考文献：
  名称：

  新型胺胍衍生物的合成，放射性标记和评价，作为N-甲基-d-天冬氨酸受体离子通道的潜在正电子发射断层显像示踪剂

  摘要：

  的Ñ -甲基- d -天冬氨酸受体（NMDAR）参与许多神经障碍和精神障碍，包括阿尔茨海默氏病和精神分裂症。这项研究的目的是开发一种正电子发射断层扫描（PET）配体，以评估NMDAR离子通道在体内的生物利用度。合成了一系列的三-N-取代的二芳基胍，并在大鼠前脑膜级分中评估了它们对NMDAR离子通道的体外结合亲和力。化合物21，23和26与任一碳-11或氟-18并放射性标记体外在Wistar大鼠中进行了生物分布和代谢物研究。生物分布研究表明，尤其是在额叶前额皮层中摄取较高，而在小脑中摄取最低。但是，用MK-801进行预处理不会降低对放射性标记配体的吸收。另外，所有三个配体均显示出快速的新陈代谢。

  DOI：

  10.1016/j.ejmech.2016.04.022

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。
• Spontaneous conversion of prenyl halides to acids: application in metal-free preparation of deuterated compounds under mild conditions
  作者：Dhanushka Darshana、Sanya Sureram、Chulabhorn Mahidol、Somsak Ruchirawat、Prasat Kittakoop

  DOI：10.1039/d1ob01275d

  日期：——

  work reports a metal-free method for deuterium labeling covering a broad range of substrate including phenolic compounds (i.e. flavonoids and stilbenes), indoles, pyrroles, carbonyl compounds, and steroids. This method was also applied for commonly used drugs such as loxoprofen, haloperidol, stanolone, progesterone, androstenedione, donepezil, ketorolac, adrenosterone, cortisone, pregnenolone, and dexamethasone

  在这里，我们揭示了一种简单的卤化氘 (DX) 生成方法，该方法由合成化学实验室中现成的普通且廉价的试剂制成，i . e . 在温和条件下，异戊二烯基、烯丙基和炔丙基卤化物。我们设想，原位生成酸卤化氘可用于酸催化反应，并可用于有机催化氘化。本工作报告了一种无金属氘标记方法，覆盖范围广泛的底物，包括酚类化合物（即. 类黄酮和芪）、吲哚、吡咯、羰基化合物和类固醇。该方法也适用于常用药物，如洛索洛芬、氟哌啶醇、甾烷酮、黄体酮、雄烯二酮、多奈哌齐、酮咯酸、肾上腺素、可的松、孕烯醇酮和地塞米松。这项工作证明了一些氘代化合物的克级无色谱合成。这项工作提供了一种简单、清洁且无副产物的位点选择性氘代，并且氘代产物无需色谱分离即可获得。当将这些引发剂用于其他酸催化反应时，DX 的氘同位素效应可能会提供不同于使用普通酸的反应所获得的产物。虽然异戊二烯卤化物自发转化为酸的机制尚不清楚，
• 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。
• 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。
• PYRROL-1-YL BENZOIC ACID DERIVATIVES USEFUL AS MYC INHIBITORS
  申请人：DANA-FARBER CANCER INSTITUTE, INC.

  公开号：US20150291521A1

  公开（公告）日：2015-10-15

  The present invention provides compounds of Formula (I-A), (I-B), and (I-C), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting Myc (e.g., c-Myc) activity. The present invention further provides methods of using the compounds described herein for treating Myc-mediated disorders (e.g., cancer and other proliferative diseases). The present invention also provides assays for identifying Myc inhibitors.

  本发明提供了公式(I-A)、(I-B)和(I-C)的化合物，其药学上可接受的盐以及其制药组合物。本发明的化合物可用于抑制Myc（例如c-Myc）的活性。本发明还提供了使用本文所描述的化合物治疗Myc介导的疾病（例如癌症和其他增殖性疾病）的方法。本发明还提供了用于鉴定Myc抑制剂的检测方法。