Imidazole

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.

Imidazole
Names
Preferred IUPAC name
1H-Imidazole
Other names
1,3-Diazole
Glyoxaline (archaic)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.473
EC Number
  • 206-019-2
KEGG
RTECS number
  • NI3325000
UNII
  • InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5) Y
    Key: RAXXELZNTBOGNW-UHFFFAOYSA-N Y
  • InChI=1/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
    Key: RAXXELZNTBOGNW-UHFFFAOYAS
  • c1cnc[nH]1
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)
UV-vis (λmax) 206 nm
Structure
Monoclinic
Planar 5-membered ring
3.61 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive
GHS labelling:
H302, H314, H360D
P263, P270, P280, P301+P310, P305+P351+P338, P308+P313
Flash point 146 °C (295 °F; 419 K)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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 a 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).

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