Indazole

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Indazole
Skeletal formula with numbering convention
Ball-and-stick model
Space-filling model
Names
Preferred IUPAC name
1H-Indazole[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.436 Edit this at Wikidata
UNII
  • InChI=1S/C7H6N2/c1-2-4-7-6(3-1)5-8-9-7/h1-5H,(H,8,9) checkY
    Key: BAXOFTOLAUCFNW-UHFFFAOYSA-N checkY
  • InChI=1/C7H6N2/c1-2-4-7-6(3-1)5-8-9-7/h1-5H,(H,8,9)
    Key: BAXOFTOLAUCFNW-UHFFFAOYAQ
  • c2ccc1[nH]ncc1c2
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).
checkY  (what is checkY☒N ?)
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]

Fischer indazole.png

Some derivatives[]

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

See also[]

References[]

  1. ^ 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.
  2. ^ 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.
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