File:Imidazole_2D_full_aromatic.svg · Wikimedia Commons · See Wikimedia Commons
imidazole
Sign in to saveAlso known as Him, IMD, N,N'-vinyleneformamidine, N,N'-1,2-ethenediylmethanimidamide, iminazole, pyrro[b]monazole, 1,3-diaza-2,4-cyclopentadiene, miazole
Imidazole (ImH) is an organic compound with the formula . It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. It can be classified as a heterocycle, specifically as a diazole.
Chemical data
- Formula
- C3H4N2
- Molecular weight
- 68.08 g/mol
- IUPAC name
- 1H-imidazole
- SMILES
- C1=CN=CN1
- InChIKey
- RAXXELZNTBOGNW-UHFFFAOYSA-N
- XLogP
- -0.1
- Polar surface area
- 28.7 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
322,708 papers- Imidazole and Derivatives Drugs Synthesis: A Review.Current organic synthesis · 2023
- Imidazole Compounds: Synthesis, Characterization and Application in Optical Analysis.Critical reviews in analytical chemistry · 2024
- Imidazole-, Triazole-, and Tetrazole-Based High-Energy Ionic Liquids.Topics in current chemistry (Cham) · 2025
- Imidazole-Based Metal Complex Derivatives: A Comprehensive Overview of Synthesis and Biological Applications.Medicinal chemistry (Shariqah (United Arab Emirates)) · 2025
- Indole-Imidazole Hybrids as Emerging Therapeutic Scaffolds: Synthetic Advances and Biomedical Applications.Molecules (Basel, Switzerland) · 2025
via PubMed
Wikidata facts
- Mass
- 68.037448
- Image
- Imidazole sample.jpg
Show 9 more facts
- chemical formula
- C₃H₄N₂
- MCN code
- 2933.29.91
- melting point
- 90.5
- Commons category
- Imidazole
- canonical SMILES
- C1=CN=CN1
- density
- 1.23
- boiling point
- 257
- electric dipole moment
- 3.8
- ionization energy
- 8.81
Sources (6)
via Wikidata · CC0
~11 min read
Article
17 sectionsContents
- Structure and properties
- Amphoterism
- Preparation
- Formation of one bond
- Formation of two bonds
- Formation of four bonds
- Formation from other heterocycles
- Biological significance and applications
- Pharmaceutical derivatives
- Industrial applications
- Coordination chemistry
- Use in biological research
- Salts of imidazole
- Related heterocycles
- Safety
- See also
- References
Imidazole (ImH) is an organic compound with the formula . It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. It can be classified as a heterocycle, specifically as a diazole.
Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.