Indazole
From Wikipedia, the free encyclopedia
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Names | |||
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IUPAC name
1H-indazole
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Identifiers | |||
271-44-3 ![]() |
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3D model (Jmol) | Interactive image | ||
ChEBI | CHEBI:36670 ![]() |
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ChEMBL | ChEMBL86795 ![]() |
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ChemSpider | 8866 ![]() |
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ECHA InfoCard | 100.005.436 | ||
PubChem | 9221 | ||
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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 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[edit]
- indazole-3-carboxylic acid
- Having a carboxylic acid group on carbon 3. Can be further modified to lonidamine.
See also[edit]
- 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[edit]
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This article includes a list of references, related reading or external links, but its sources remain unclear because it lacks inline citations. (January 2011) (Learn how and when to remove this template message) |
- 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.
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