1-(4-氰苯基)-2,5-二甲基吡咯 | 119516-86-8

• 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-(4-氰苯基)-2,5-二甲基吡咯
• 中文别名: 1-(4-苯氰基)-2,5-二甲基吡咯
• 英文名称: 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzonitrile
• 英文别名: 1-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole；1-(4-Cyanophenyl)-2,5-dimethylpyrrole；4-(2,5-dimethylpyrrol-1-yl)benzonitrile
• CAS: 119516-86-8
• 化学式: C₁₃H₁₂N₂
• mdl: MFCD03228548
• 分子量: 196.252
• InChiKey: FNDFKQYZEDOHRC-UHFFFAOYSA-N

物化性质

• 熔点：
  110 °C
• 沸点：
  345.9±30.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  6.1
• 海关编码：
  2933990090
• 危险品运输编号：
  UN 2811
• 储存条件：
  室温

SDS

1-(4-Cyanophenyl)-2,5-dimethylpyrrole
SAFETY DATA SHEET

---

Section 1. IDENTIFICATION
Product name: 1-(4-Cyanophenyl)-2,5-dimethylpyrrole

---

Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Acute toxicity (Oral) Category 3
Category 3
Acute toxicity (Dermal)
Acute toxicity (Inhalation) Category 3
Category 2
Skin corrosion/irritation
Serious eye damage/eye irritation Category 2A
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Danger
Toxic if swallowed, in contact with skin or if inhaled
Hazard statements
Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Avoid breathing dust/fume/gas/mist/vapours/spray.
[Prevention]
Use only outdoors or in a well-ventilated area.
Do not eat, drink or smoke when using this product.
Wash hands thoroughly after handling.
Wear protective gloves and eye/face protection.
[Response] IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for
breathing. Call a POISON CENTER or doctor/physician.
IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. Rinse
mouth.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Remove/Take off immediately all contaminated clothing.
Wash contaminated clothing before reuse.
Call a POISON CENTER or doctor/physician if you feel unwell.
1-(4-Cyanophenyl)-2,5-dimethylpyrrole

---

Section 2. HAZARDS IDENTIFICATION
[Storage] Store in a well-ventilated place. Keep container tightly closed.
Store locked up.
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government.

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 1-(4-Cyanophenyl)-2,5-dimethylpyrrole
>98.0%(GC)
Percent:
CAS Number: 119516-86-8
2,5-Dimethyl-1-(4-cyanophenyl)pyrrole
Synonyms:
Chemical Formula: C13H12N2

---

Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Call a POISON CENTER or doctor/physician.
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. Call a POISON CENTER or doctor/physician.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Immediately call a POISON CENTER or doctor/physician. Rinse mouth.
Ingestion:
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

---

Section 5. FIRE-FIGHTING MEASURES
Dry chemical, foam, water spray, carbon dioxide.
Suitable extinguishing
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
When extinguishing fire, be sure to wear personal protective equipment.
Special protective
equipment for firefighters:

---

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use extra personal protective equipment (P3 filter respirator for toxic particles). Keep
protective equipment and people away from and upwind of spill/leak. Entry to non-involved personnel should
emergency procedures: be controlled around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

---

Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a closed system if possible. Use a local exhaust if dust or aerosol will be
generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Keep container tightly closed. Store in a cool, dark and well-ventilated place.
Storage conditions:
1-(4-Cyanophenyl)-2,5-dimethylpyrrole

---

Section 7. HANDLING AND STORAGE
Store locked up.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

---

Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator, self-contained breathing apparatus(SCBA), supplied air respirator,
etc. Use respirators approved under appropriate government standards and follow
local and national regulations.
Hand protection: Impervious gloves.
Eye protection: Safety goggles. A face-shield, if the situation requires.
Skin and body protection: Impervious protective clothing. Protective boots, if the situation requires.

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
Colour: Yellow - Deep reddish yellow
Odour: No data available
pH: No data available
Melting point/freezing point:110°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
No data available
Relative density:
Solubility(ies):
[Water] No data available
[Other solvents]
Methanol
Soluble:

---

Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Hydrogen cyanide
products:

---

Section 11. TOXICOLOGICAL INFORMATION
No data available
Acute Toxicity:
Skin corrosion/irritation: No data available
No data available
Serious eye
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

---

Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
1-(4-Cyanophenyl)-2,5-dimethylpyrrole

---

Section 12. ECOLOGICAL INFORMATION
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
No data available
Log Pow:
Soil adsorption (Koc): No data available
No data available
Henry's Law
constant(PaM3/mol):

---

Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

---

Section 14. TRANSPORT INFORMATION
6.1: Toxic substance.
Hazards Class:
UN-No: 2811
Toxic solid, organic, n.o.s.
Proper shipping name:
Packing group: III

---

Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-(4-氰苯基)-2,5-二甲基吡咯 在 溶剂黄146 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 18.33h， 生成 N-[[1-(4-cyanophenyl)-2,5-dimethylpyrrol-3-yl]methyl]cyclohexanamine
  参考文献：
  名称：

  Improving the Potency of N-Aryl-2,5-dimethylpyrroles against Multidrug-Resistant and Intracellular Mycobacteria

  摘要：

  A series of N-phenyl-2,5-dimethylpyrrole derivatives, designed as hybrids of the antitubercular agents BM212 and SQ109, have been synthesized and evaluated against susceptible and drug-resistant mycobacteria strains. Compound 5d, bearing a cyclohexylmethylene side chain, showed high potency against M. tuberculosis including MDR-TB strains at submicromolar concentrations. The new compound shows bacteriostatic activity and low toxicity and proved to be effective against intracellular mycobacteria too, showing an activity profile similar to isoniazid.

  DOI：

  10.1021/acsmedchemlett.9b00515
• 作为产物：
  描述：

  2,5-己二酮 、 对硝基苯甲腈 在 indium 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以40%的产率得到1-(4-氰苯基)-2,5-二甲基吡咯
  参考文献：
  名称：

  Indium-mediated one-pot pyrrole synthesis from nitrobenzenes and 1,4-diketones

  摘要：

  One-pot reduction-triggered heterocyclizations of nitrobenzene derivatives with 1,4-diketones were investigated. In the presence of indium/AcOH in toluene at 80 degrees C, reaction of nitrobenzenes with 2,5-hexadione produced moderate to excellent yields (40-98%) of the corresponding pyrroles within 1.5-24 h depending on the substituents of the starting materials. Similarly, the reaction of nitrobenzenes with 1-phenyl-1,4-pantanedione in the presence of indium/AcOH in toluene at reflux afforded the corresponding pyrroles within 0.5-24 h with 60-98% yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.113

文献信息

• One-pot synthesis of N-substituted pyrroles from nitro compounds and 2,5-hexadione over a heterogeneous cobalt catalyst
  作者：Zheng Gong、Yu Lei、Peng Zhou、Zehui Zhang

  DOI：10.1039/c7nj01898c

  日期：——

  study, the one-pot heterocyclization of nitro compounds with 2,5-hexadione was studied for the synthesis of N-substituted pyrroles via a Paal–Knorr condensation process. The heterogeneous cobalt–nitrogen catalyst (Co–Nx/C-800-AT) was found to be active for this reaction with formic acid. Formic acid served as a hydrogen donor for the transfer hydrogenation, and also acted as an acid catalyst. More importantly

  在这项研究中，研究了通过Paal–Knorr缩合过程将硝基化合物与2，5-己二酮进行一锅法杂环合成N-取代的吡咯。发现多相钴-氮催化剂（Co-N x / C-800-AT）在与甲酸的该反应中具有活性。甲酸用作转移加氢的氢供体，也用作酸催化剂。更重要的是，该方法对其他官能团具有耐受性，因此以高至优异的产率制备了各种N-取代的吡咯。Co-N x / C-800-AT催化剂非常稳定，可以重复使用几次而不会损失其催化活性。
• Imidazolium Triflate Ionic Liquid Improves the Activity of ZnCl₂ in the Synthesis of Pyrroles and Ketones
  作者：Hai Truong Nguyen、Dung Kim Thi Ngo、Khiem Duy Nguyen Chau、Phuong Hoang Tran

  DOI：10.1080/00304948.2020.1868910

  日期：2021.3.4

  (2021). Imidazolium Triflate Ionic Liquid Improves the Activity of ZnCl2 in the Synthesis of Pyrroles and Ketones. Organic Preparations and Procedures International: Vol. 53, No. 2, pp. 157-165.

  （2021年）。三氟甲磺酸咪唑鎓离子液体可提高ZnCl2在吡咯和酮合成中的活性。国际有机制剂和程序：Vol。53，第2号，第157-165页。
• [EN] ANDROGEN RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RÉCEPTEUR DES ANDROGÈNES
  申请人：ALPINE ANDROSCIENCES INC

  公开号：WO2019152731A1

  公开（公告）日：2019-08-08

  Compounds that inhibit the androgen receptor, pharmaceutical compositions comprising one or more of the compounds, as well as methods of treating cancer using such compounds are described.

  描述了抑制雄激素受体的化合物、包含一种或多种这些化合物的药物组合物，以及使用这些化合物治疗癌症的方法。
• Polystyrene-supported GaCl3 as a highly efficient and recyclable heterogeneous Lewis acid catalyst for one-pot synthesis of N-substituted pyrroles
  作者：Ali Rahmatpour

  DOI：10.1016/j.jorganchem.2012.03.025

  日期：2012.8

  of N-substituted pyrroles from one-pot condensation reaction of 2,5-hexanedione with amines and diamines in the presence of polystyrene-supported gallium trichloride (PS/GaCl3) as a highly active and reusable heterogeneous Lewis acid catalyst is presented. This new protocol has the advantages of easy availability, stability, reusability and eco-friendly of the catalyst, high to excellent yields, simple

  在高活性聚苯乙烯负载的三氯化镓（PS / GaCl 3）存在下，由2,5-己二酮与胺和二胺进行一锅缩合反应制备N-取代吡咯的一种新的环境友好方法。提出了可重复使用的多相路易斯酸催化剂。该新方案的优点是容易获得，稳定，可重复使用且对催化剂生态友好，产率高至优异，实验和后处理程序简单。
• A green and efficient method for the synthesis of pyrroles using a deep eutectic solvent ([CholineCl][ZnCl₂]₃) under solvent-free sonication
  作者：Hai Truong Nguyen、Duy-Khiem Nguyen Chau、Phuong Hoang Tran

  DOI：10.1039/c7nj02396k

  日期：——

  An efficient deep eutectic solvent-based synthesis of pyrroles under ultrasound irradiation has been developed to provide a significant improvement of the yield up to 99% in a short reaction time. The synthesis of pyrroles is highly atom-economical, producing water as the sole byproduct. In addition, [CholineCl][ZnCl2]3 is easily synthesized from commercially available choline chloride and zinc chloride

  已经开发了在超声辐射下有效的基于深共熔溶剂的吡咯的合成，以在短的反应时间内显着提高收率高达99％。吡咯的合成是高度原子经济的，产生水作为唯一的副产物。另外，[CholineCl] [ZnCl 2 ] 3可以通过市售的氯化胆碱和氯化锌，通过具有成本效益且对环境无害的途径容易地合成。通过FT-IR，1 H-NMR，13 C-NMR，HRMS（ESI），拉曼和TGA对得到的[CholineCl] [ZnCl 2 ] 3进行了表征。通过现有方法合成了五种新的吡咯。此外，[胆碱Cl] [ZnCl2 ] 3最多可重复使用四次，而不会显着降低催化活性。