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Chemical compound From Wikipedia, the free encyclopedia
Indazole, also called isoindazole, is a heterocyclic aromatic organic compound. This bicyclic compound consists of the fusion of benzene and pyrazole.
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Names | |||
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Preferred IUPAC name
1H-Indazole[1] | |||
Identifiers | |||
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ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.005.436 | ||
PubChem CID |
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UNII | |||
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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Indazole is an amphoteric molecule which can be protonated to an indazolium cation or deprotonated to an indazolate anion. The corresponding pKa values are 1.04 for the equilibrium between indazolium cation and indazole and 13.86 for the equilibrium between indazole and indazolate anion.[2]
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.[3]
Indazole, C7H6N2, was obtained by E. Fischer (Ann. 1883, 221, p. 280) by heating ortho-hydrazine cinnamic acid,[4]
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