Indazole

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Indazole
Skeletal formula with numbering convention
Ball-and-stick model
Space-filling model
Names
IUPAC name
1H-indazole
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.436
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.

Indazole, C7H6N2, was obtained by E. Fischer (Ann. 1883, 221, p. 280) by heating ortho-hydrazine cinnamic acid,[1]

C6H4Langle.svg CH = CH·COOH =C2H4O2+C7H6N2.
NH·NH2

Some derivatives[edit]

indazole-3-carboxylic acid

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

See also[edit]

References[edit]

  1. ^ Wikisource Chisholm, Hugh, ed. (1911). "Indazoles". 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.