Indazole

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Indazole
Skeletal formula with numbering convention
Ball-and-stick model Space-filling model
Identifiers
CAS number 271-44-3 YesY
PubChem 9221
ChemSpider 8866 YesY
ChEBI CHEBI:36670 YesY
ChEMBL CHEMBL86795 YesY
Jmol-3D images Image 1
Properties
Molecular formula C7H6N2
Molar mass 118.14 g/mol
Melting point 147-149 °C
Boiling point 270 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Indazole, also called benzpyrazole or isoindazone, is a heterocyclic aromatic organic compound.

Indazole derivatives display a broad variety of biological activities.

Indazoles are rare in nature. The alkaloids Nigellicine, Nigeglanine, and Nigellidine are indazoles. Nigellicine was isolated from the widely distributed plant Nigella sativa L. (black cumin). Nigeglanine was isolated from extracts of Nigella glandulifera. The Davis–Beirut reaction can generate 2H-indazoles.

See also[edit]

References[edit]

  • Synthesis: W. Stadlbauer, in Science of Synthesis 2002, 12, 227, and W. Stadlbauer, in Houben-Weyl, 1994, E8b, 764.
  • Review: A. Schmidt, A. Beutler, B. Snovydovych, Recent Advances in the Chemistry of Indazoles, Eur. J. Org. Chem. 2008, 4073 – 4095.