Indazole

Indazole
IUPAC name 1H-indazole
Identifiers
CAS number	271-44-3 Y
PubChem	9221
ChemSpider	8866 Y
ChEBI	CHEBI:36670 Y
ChEMBL	CHEMBL86795 Y
Jmol-3D images	Image 1
SMILES n2cc1ccccc1n2
InChI InChI=1S/C7H6N2/c1-2-4-7-6(3-1)5-8-9-7/h1-5H,(H,8,9) Y Key: BAXOFTOLAUCFNW-UHFFFAOYSA-N Y InChI=1/C7H6N2/c1-2-4-7-6(3-1)5-8-9-7/h1-5H,(H,8,9) Key: BAXOFTOLAUCFNW-UHFFFAOYAQ
Properties
Molecular formula	C7H6N2
Molar mass	118.14 g/mol
Melting point	147-149 °C
Boiling point	270 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 alkalids 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.

See also

• Indole, an analog with only one nitrogen atom in position 1.
• Benzimidazole, an analog with the nitrogen atoms in positions 1 and 3.
• Simple aromatic rings
• 7-Nitroindazole, an indazole-based nitric oxide synthase inhibitor

References

• 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.