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Topic summary

Imidazole

Imidazole
Names Preferred IUPAC name
1H-Imidazole
Other names
1,3-Diazole
Glyoxaline (archaic)
Identifiers
3D model (JSmol)
103853 ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.005.473EC Number
  • 206-019-2
1417 KEGG
RTECS number
  • NI3325000
UNII
UN number3263
  • InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
    Key: RAXXELZNTBOGNW-UHFFFAOYSA-N
  • InChI=1/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
  • c1cnc[nH]1
Properties C3H4N2Molar mass68.077 g/mol Appearance White or pale yellow solid Density1.23 g/cm, solid Melting point89 to 91 °C (192 to 196 °F; 362 to 364 K) Boiling point256 °C (493 °F; 529 K) 633 g/L Acidity (pKa) 6.95 (for the conjugate acid) UV-vis (λmax) 206 nm Structure MonoclinicPlanar 5-membered ring 3.61 DHazards Occupational safety and health (OHS/OSH):
Main hazards
Corrosive GHS labelling: DangerH302, H314, H360DP263, P270, P280, P301+P310, P305+P351+P338, P308+P313Flash point146 °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 (CH)2NHCHN. 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.

When fused to a pyrimidine ring, it forms purine, which is the most widely occurring nitrogen-containing heterocycle in nature.

The name "imidazole" was coined in 1887 by the German chemist Arthur Rudolf Hantzsch (1857–1935).

Wikipedia source