Cinnoline

Structural formula
General
Surname	Cinnoline
other names	1,2-benzodiazine 1,2-diazanaphthalene Benzo [ c ] pyridazine α-phenodiazine 1,2-naphthyridine
Molecular formula	C 8 H 6 N 2
Brief description	colorless needles
External identifiers / databases
CAS number 253-66-7 EC number 205-964-8 ECHA InfoCard 100.005.423 PubChem 9208 Wikidata Q413130
properties
Molar mass	130.15 g mol −1
Physical state	firmly
Melting point	40-41 ° C
boiling point	114 ° C (0.4 hPa )
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cinnoline is an organic compound that belongs to the heterocycles (more precisely: heteroaromatics and diazanaphthalenes ). The compound consists of a benzene ring to which a pyridazine ring is fused . Cinnoline is isomeric to quinazoline , quinoxaline and phthalazine .

Manufacturing

The synthesis of cinnoline is achieved through the electrolysis of (2-nitrophenethyl) propylamine. The reaction is carried out in a buffered mixture of methanol and water and gives cinnoline in moderate yield:

Cinnoline derivatives can also be produced using the Neber-Bössel synthesis . It is z. B. 2- (2-aminophenyl) -2- hydroxyacetic acid ( 1 , R = H) converted to 3-hydroxylcinnoline ( 2 , R = H):

Derivatives

Cinnoline is the starting structure for many derivatives.

• Cinnoline hydrochloride C ₈ H ₆ N ₂ · HCl, CAS number: 5949-24-6
• Cinnoline-4-carboxylic acid C ₉ H ₆ N ₂ O ₂ , CAS number: 21905-86-2
• 4 (1 H ) -Cinnolinone C ₈ H ₆ N ₂ O, CAS number: 18514-84-6
• Benzo [ c ] cinnoline C ₁₂ H ₈ N ₂ , CAS number: 34524-78-2
• Cinoxacin (an antibiotic )

Individual evidence

1. ↑ M. Busch, A. Rast: Ueber das Cinnolin. , Chem. Ber. , 1897 , 30 , pp. 521-527 ( doi : 10.1002 / cber.189703001103 ).
2. ↑ ^{a b} J. S. Morley: Cinnolines. Part XX VII. The Preparation and Nitration of Cinnoline. , J. Chem. Soc. , 1951 , pp. 1971-1975.
3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
4. ↑ BA Frontana-Uribe, C. Moinet, L. Toupet, Eur. J. Org. Chem. 1999 , 2 , 419-430.
5. ^ Zerong Wang: Comprehensive Organic Name Reactions and Reagents, Volume 2 . John Wiley, Hoboken (NJ) 2009, ISBN 978-0-470-28662-3 , pp. 2022-2024 .
6. ↑ Cinnoline derivatives at Chemicalland21 .