Indazole
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Names | |||
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Preferred IUPAC name
1H-Indazole[1] | |||
Identifiers | |||
3D model (JSmol)
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ChEBI | |||
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ECHA InfoCard | 100.005.436 ![]() | ||
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |||
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 , , and are indazoles. Nigellicine was isolated from the widely distributed plant Nigella sativa L. (black cumin). Nigeglanine was isolated from extracts of .
The Davis–Beirut reaction can generate 2H-indazoles.
Indazole, C7H6N2, was obtained by E. Fischer (Ann. 1883, 221, p. 280) by heating ortho-hydrazine cinnamic acid,[2]
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[]
- ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 213. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
- ^ Chisholm, Hugh, ed. (1911). Encyclopædia Britannica. 14 (11th ed.). Cambridge University Press. p. 371. .
- 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.
Categories:
- Indazoles
- Simple aromatic rings