1092776-44-7

Basic information

• Product Name: 3-bromo-1,2-dimethylindazolium bromide
• Synonyms: 3-bromo-1,2-dimethylindazolium bromide
• CAS NO: 1092776-44-7
• Molecular Weight: 306
• Mol File: 1092776-44-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-bromo-1,2-dimethylindazolium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-bromo-1,2-dimethylindazolium bromide(1092776-44-7)
• EPA Substance Registry System: 3-bromo-1,2-dimethylindazolium bromide(1092776-44-7)

Safety Data

• Hazardous Substances Data: 1092776-44-7(Hazardous Substances Data)

Upstream product

• 859217-21-3 1,2-dimethyl-1H-indazol-2-ium-3-carboxylate 
• 42974-18-5 3,4-dibromo-3,4-dihydrocoumarin 
• 1114-30-3 diethyl 2,3-dibromosuccinate 
• 611-91-6 2,3-dibromo-1,3-diphenylpropane-1-one 
• 19521-13-2 α,β-dibromo-β-phenylpropionitrile 
• 21770-48-9 methyl 2,3-dibromo-3-phenylpropanoate 
• 19922-77-1 1,2,4,5-tetrabromo-1,5-diphenyl-3-pentanone 
• 854029-40-6 4,5-dibromo-1,5-diphenyl-pent-1-en-3-one 

Relevant articles and documents

N-heterocyclic carbenes of indazole: Ring enlargement reactions by α-halo ketones and dehalogenations of vicinal dihalides

On decarboxylation, 1,2-dimethylindazolium-3-carboxylate forms the N-heterocyclic carbene, 1,2-dimethylindazol-3-ylidene, which deprotonates α-halo ketones. The resulting indazolium salt and the corresponding enolate form 1:1 adducts which undergo a ring enlargement to cinnolines. Reaction with 2-bromo-2,3-dihydro-1H-inden-1-one gives a 4- hydroxyspiro[cinnoline-3,2′-inden]-1′-one by ring enlargement reaction (X-ray crystal structure analysis). Vicinal dibromides undergo debromination under these conditions to give alkenes, and substrates with 1,2-dibromoethene partial structure give acetylenes. As 3-bromoindazole is found as the second product of this reaction, an E1cb mechanism, initiated by Br+ abstraction by the N-heterocyclic carbene of indazole, is suggested. Georg Thieme Verlag Stuttgart.