Indazole

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Structural formula
Structural formula of indazole
General
Surname Indazole
other names
  • 1 H -indazole
  • 1,2-benzopyrazole
  • 1,2-benzodiazole
  • Isoindazone
Molecular formula C 7 H 6 N 2
Brief description

colorless solid

External identifiers / databases
CAS number 271-44-3
EC number 205-978-4
ECHA InfoCard 100.005.436
PubChem 9221
ChemSpider 8866
Wikidata Q417106
properties
Molar mass 118.14 g · mol -1
Physical state

firmly

Melting point

146-149 ° C

boiling point

270 ° C (994 h Pa )

solubility

soluble in hot water

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Indazole is an aromatic heterocycle and forms the basic structure of a few natural substances (nigellicin, nigellidine and nigeglanin from Nigella sp. ).

Occurrence

Derivatives of indazole occur rarely in nature. Nigellicin, nigeglanin and nigellidine are natural substances that contain the indazole ring. Nigellicin is an alkaloid from Nigella sativa L. (black cumin) and belongs to the substance class of the mesomeric betaines. Nigeglanin was isolated from Nigella glandulifera .

presentation

The indazoles are produced, for example, via the Jacobson indazole synthesis (see scheme below).

Representation of indazole

use

Indazole is important for the production of certain dyes . Derivatives of indazole are also of interest in pharmacology. 1-Benzyl-3- (3-dimethylaminopropoxy) -1 H -indazole ( benzydamine ) is used for painful inflammation of the mucous membranes because of its local anesthetic and anti-inflammatory effects .

literature

  • Synthesis (simplified, after Jacobson): Synthesis , 1972 , Issue 07, p. 375; doi : 10.1055 / s-1972-21885 .
  • Synthesis methods: W. Stadlbauer, in Science of Synthesis 2002, 12, 227.
  • Synthesis methods: W. Stadlbauer, in Houben-Weyl, 1994, E8b, 764.
  • Review article (synthesis, properties, biol. Activities etc.): A. Schmidt, A. Beutler, B. Snovydovych, Recent Advances in the Chemistry of Indazoles , Eur. J. Org. Chem . 2008 , 4073-4095.

Individual evidence

  1. ↑ a b c d e f data sheet 1H-indazole, 99% from AlfaAesar, accessed on December 7, 2019 ( PDF )(JavaScript required) .
  2. ↑ Data sheet Indazol from Acros, accessed on February 24, 2010.
  3. ^ Harry Auterhoff : Textbook of Pharmaceutical Chemistry , Wissenschaftliche Verlagsgesellschaft, Stuttgart 1968.