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Names | |||
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Preferred IUPAC name
1H-Imidazole[1] | |||
Other names
1,3-Diazole
Glyoxaline (archaic) | |||
Identifiers | |||
3D model (JSmol)
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103853 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard | 100.005.473 | ||
EC Number |
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1417 | |||
KEGG | |||
PubChem CID
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RTECS number |
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UNII | |||
UN number | 3263 | ||
CompTox Dashboard (EPA)
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Properties | |||
C3H4N2 | |||
Molar mass | 68.077 g/mol | ||
Appearance | White or pale yellow solid | ||
Density | 1.23 g/cm3, solid | ||
Melting point | 89 to 91 °C (192 to 196 °F; 362 to 364 K) | ||
Boiling point | 256 °C (493 °F; 529 K) | ||
633 g/L | |||
Acidity (pKa) | 6.95 (for the conjugate acid) [2] | ||
UV-vis (λmax) | 206 nm | ||
Structure | |||
Monoclinic | |||
Planar 5-membered ring | |||
3.61 D | |||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards
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Corrosive | ||
GHS labelling:[4] | |||
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Danger | |||
H302, H314, H360D | |||
P263, P270, P280, P301+P310, P305+P351+P338, P308+P313[3] | |||
Flash point | 146 °C (295 °F; 419 K) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Imidazole (ImH) is an organic compound with the formula C3N2H4. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole, and has non-adjacent nitrogen atoms in meta-substitution.
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.[5][6][7][8][9]
When fused to a pyrimidine ring, it forms a purine, which is the most widely occurring nitrogen-containing heterocycle in nature.[10]
The name "imidazole" was coined in 1887 by the German chemist Arthur Rudolf Hantzsch (1857–1935).[11]
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