4-Methylimidazole - ≥98% , CAS No.822-36-6

CAS: 822-36-6 Cat. No.: M112296 Molecular Weight: 82.11 Beilstein Registry Number: 1453 EC Number: 212-497-3

GRADE & PURITY ≥98%

Synonyms

PD002162 | 4-METHYLIMIDAZOLE [HSDB] | 4-methyl-1(3)H-imidazole | 5-Methyl-1H-imidazole | NCGC00091437-01 | BDBM50538684 | 4-methyl imidazole | Tox21_201048 | AL-398/25017073 | CCRIS 8912 | AI3-08274 | IMIDAZOLE, 4-METHYL- | CAS-822-36-6 | 4MZ | EC 212-497

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

4(5)-Methylimidazole was quantified in coffee by GC-MS method.

Specifications

Synonyms

PD002162 | 4-METHYLIMIDAZOLE [HSDB] | 4-methyl-1(3)H-imidazole | 5-Methyl-1H-imidazole | NCGC00091437-01 | BDBM50538684 | 4-methyl imidazole | Tox21_201048 | AL-398/25017073 | CCRIS 8912 | AI3-08274 | IMIDAZOLE, 4-METHYL- | CAS-822-36-6 | 4MZ | EC 212-497

Specifications & Purity

≥98%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1=CN=CN1
• IUPAC Name: 5-methyl-1H-imidazole
• InChIKey: XLSZMDLNRCVEIJ-UHFFFAOYSA-N
• INCHI: 1S/C4H6N2/c1-4-2-5-3-6-4/h2-3H,1H3,(H,5,6)
• Isomeric SMILES: CC1=CN=CN1
• WGK Germany: 2
• RTECS: NI7350000
• UN Number: 3263
• Molecular Weight: 82.11
• Beilstein: 1453
• Reaxy-Rn: 605627
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=605627&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Azoles
      • Subclass Imidazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Azoles
• Subclass: Imidazoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Imidazoles
• Alternative Parents: Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Heteroaromatic compound - Imidazole - Azacycle - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as imidazoles. These are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.
• External Descriptors: imidazoles

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

AR Tclin Androgen Receptor (11781 Activities)

Discover Target: AR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

Discover Target: ALDH1A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Lymphoblastoid cell (5959 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

QPCT Tchem Glutaminyl-peptide cyclotransferase (1121 Activities)

Discover Target: QPCT

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GMNN Tbio Geminin (128009 Activities)

Discover Target: GMNN

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water.
• Sensitivity: Hygroscopic,Air Sensitive.
• Flash Point(°C): 157 °C - closed cup
• Boil Point(°C): 263°C
• Melt Point(°C): 56°C
• Molecular Weight: 82.100 g/mol
• XLogP3: 0.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 82.0531 Da
• Monoisotopic Mass: 82.0531 Da
• Topological Polar Surface Area: 28.700 Ų
• Heavy Atom Count: 6
• Formal Charge: 0
• Complexity: 44.800
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Rihui Su, Xiaohua Xiao, Gongke Li.  (2023)  Thermosensitive poly(N-isopropylacrylamide) hydrogel/highly internal phase emulsion porous polymer tube tip solid-phase extraction for the determination of methylimidazoles in beverage.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:37924617] [10.1016/j.chroma.2023.464476]

2. Mincong Zhu, Mingqiang Huang, Tingting Lu, Shunyou Cai, Xiaobin Shan, Liusi Sheng, Weixiong Zhao, Xuejun Gu, Weijun Zhang.  (2022)  Experimental study on the imidazoles of aqueous secondary organic aerosol formed from reaction of methylglyoxal and ammonium sulphate.  Atmospheric Pollution Research,      [PMID:] [10.1016/j.apr.2022.101535]

3. Ke Li, Hao Fang, Xiuzhi Duan, Dongshun Deng.  (2021)  Efficient uptake of NH3 by dual active sites NH4SCN-imidazole deep eutectic solvents with low viscosity.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2021.116724]

4. Jiajia Liu, Xiaochen Tang, Huiling Lu, Yingjie Xu.  (2021)  Insight into the Interactions between Azole-Anion-Based Ionic Liquids and Propargylic Alcohol: Influence on the Carboxylative Cyclization of Propargylic Alcohol with Carbon Dioxide.  ACS Sustainable Chemistry & Engineering,      [PMID:] [10.1021/acssuschemeng.0c08653]

5. Yongjie Zhang, Ning Feng, Shujin Zhou, Xia Xin.  (2021)  Fluorescent nanocomposites based on gold nanoclusters for metal ion detection and white light emitting diodes.  Nanoscale,  13  (7): (4140-4150).  [PMID:33575692] [10.1039/D0NR09141C]

6. Dan Li, Yong Kang, Jie Li, Zongchi Wang, Zhinan Yan, Kai Sheng.  (2020)  Chemically tunable DILs: Physical properties and highly efficient capture of low-concentration SO2.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2020.116572]

7. Chaoyue Zhao, Xianliang Qiao, Zenghuimin Yi, Qingxin Guan, Wei Li.  (2020)  Active centre and reactivity descriptor of a green single component imidazole catalyst for acetylene hydrochlorination.  PHYSICAL CHEMISTRY CHEMICAL PHYSICS,  22  (5): (2849-2857).  [PMID:31967628] [10.1039/C9CP06005G]

8. Lin Yanke, Wang Shuai, Zhou Ziyue, Guo Lianxia, Yu Fangjun, Wu Baojian.  (2019)  Bmal1 regulates circadian expression of cytochrome P450 3a11 and drug metabolism in mice.  Communications Biology,  2  (1): (1-11).  [PMID:31633069] [10.1038/s42003-019-0607-z]

9. Zhike Wang, Cunling Ye, Juan Li, Heping Wang, Han Zhang.  (2013)  Comparison and evaluation of five types of imidazole-modified silica adsorbents for the removal of 2,4-dinitrophenol from water samples with the methyl group at different positions of imidazolium ring.  JOURNAL OF HAZARDOUS MATERIALS,      [PMID:23892162] [10.1016/j.jhazmat.2013.06.061]

10. Yurou Shao, Yangyang Jiang, Dong Wang, Benshuai Guo, Jingyan Zhao, Zhibin Zhou, Jianqiu Chen, Ruixin Guo, Yuntao Lei, Lili Jin.  (2024)  A facile synthesis of trioctylphosphine oxide-based azole deep eutectic solvents: Efficient reversible CO2 capture.  FUEL,      [PMID:] [10.1016/j.fuel.2024.132534]

11. Bin Chen, Hegang Shu, Yujun Guo, Yingjie Xu.  (2024)  CO2 capture and viscosity of metal chelate-based ionic liquids: Influence of the structure and substitution of the azole-based anion.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2024.126574]

12. Yifei Ma, Lijie Zhang, Hong Yang, Shanshan Zhu, Jinhua Liu.  (2025)  Imidazole-triggered in situ fluorescence reaction system for quantitatively determination of dopamine from multiple sources.  TALANTA,      [PMID:40157196] [10.1016/j.talanta.2025.127975]

13. Dongfei Zhang, Ao Wang, Wenkai Liu, Ao Zhen, Jiehua Li, Feng Luo, Xianglong Han, Zhen Li, Hong Tan.  (2024)  Self-Catalysis Highly Reversible Imidazole-Based Dynamic Covalent Polyurethane-Ureas.  MACROMOLECULES,      [PMID:] [10.1021/acs.macromol.4c00149]