Indazole

Indazole

Names
IUPAC name 1H-indazole
Identifiers
CAS Number	271-44-3
3D model (Jmol)	Interactive image
ChEBI	CHEBI:36670
ChEMBL	ChEMBL86795
ChemSpider	8866
ECHA InfoCard	100.005.436
PubChem	9221
InChI InChI=1S/C7H6N2/c1-2-4-7-6(3-1)5-8-9-7/h1-5H,(H,8,9) Key: BAXOFTOLAUCFNW-UHFFFAOYSA-N InChI=1/C7H6N2/c1-2-4-7-6(3-1)5-8-9-7/h1-5H,(H,8,9) Key: BAXOFTOLAUCFNW-UHFFFAOYAQ
SMILES n2cc1ccccc1n2
Properties
Chemical formula	C7H6N2
Molar mass	118.14 g/mol
Melting point	147 to 149 °C (297 to 300 °F; 420 to 422 K)
Boiling point	270 °C (518 °F; 543 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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Infobox references

Indazole, also called isoindazole, is a heterocyclic aromatic organic compound. This bicyclic compound consists of the fusion of benzene and pyrazole.

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.

Some derivatives

indazole-3-carboxylic acid

Having a carboxylic acid group on carbon 3. Can be further modified to lonidamine.

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.