7385-89-9

Basic information

• Product Name: 7-Iodo-8-quinolinol
• Synonyms: 7-Iodo-8-quinolinol;7-Iodoquinolin-8-ol
• CAS NO: 7385-89-9
• Molecular Formula: C₉H₆INO
• Molecular Weight: 271.05451
• Mol File: 7385-89-9.mol

Chemical Properties

• Melting Point: 133-134 °C(Solv: methanol (67-56-1); water (7732-18-5))
• Boiling Point: 319.1±22.0 °C(Predicted)
• Appearance: /
• Density: 1.974±0.06 g/cm3(Predicted)
• PKA: 2.82±0.50(Predicted)
• CAS DataBase Reference: 7-Iodo-8-quinolinol(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Iodo-8-quinolinol(7385-89-9)
• EPA Substance Registry System: 7-Iodo-8-quinolinol(7385-89-9)

Safety Data

• Hazardous Substances Data: 7385-89-9(Hazardous Substances Data)

Upstream product

• 148-24-3 8-quinolinol 
• 83-73-8 5,7-diiodo-8-hydroxyquinoline 

Downstream Products

• 130-26-7 5-chloro-7-iodoquinolin-8-ol 
• 52793-99-4 8-hydroxy-7-phenylquinoline 
• 892878-93-2 8-(tert-butyldimethylsilyloxy)-7-styrylquinoline 
• 892878-89-6 8-(tert-butyldimethylsilyloxy)-7-phenylquinoline 

Relevant articles and documents

A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines

An operationally simple and metal-free protocol for geometrically inaccessible C5-H halogenation of a range of 8-substituted quinoline derivatives has been established. The reaction proceeds under air, with inexpensive and atom economical trihaloisocyanuric acid as a halogen source (only 0.36 equiv.), at room temperature. Exceptionally high generality with respect to quinoline is observed, and in most instances, the reaction proceeded with complete regioselectivity. Quinoline with a variety of substituents at the 8-position gave, exclusively, the C5-halogenated product in good to excellent yields. Phosphoramidates, tertiary amides, N-alkyl/N,N-dialkyl, and urea derivatives of quinolin-8-amine as well as alkoxy quinolines were halogenated at the C5-position via remote functionalization for the first time. This methodology provides a highly economical route to halogenated quinolines with excellent functional group tolerance, thus providing a good complement to existing remote functionalization methods of quinolin-8-amide derivatives and broadening the field of remote functionalization. The utility of the method is further showcased through the synthesis of several compounds of biological and pharmaceutical interest.

PURIFICATION TAGS OF SYNTHETIC PEPTIDES AND PROTEINS

The present invention relates to a series of compounds useful for effecting purification, in particular for use in purification of synthetic peptides and proteins. The compounds of the invention are particularly efficient at securely anchoring peptides or

Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7- diiodoquinoline under aminocarbonylation conditions

Various 5-carboxamido-7-iodo-8-benzyloxyquinolines were synthesised via selective aminocarbonylation of 5,7-diiodo-8-benzyloxyquinoline in the presence of 'in situ' generated palladium(0) catalysts. Under similar conditions (50 °C, 80 bar CO), 5,7-bis(N-tert-butyl-glyoxylamido)-8-hydroxyquinoline was obtained using tert-butylamine as N-nucleophile. The unprotected 5,7-diiodo-8-hydroxyquinoline underwent dehydroiodination resulting in 8-hydroxyquinoline as the major product.

A straightforward methodology for the introduction of aryl and vinyl substituents in the 5 or 7 position of 8-hydroxyquinoline

A straightforward and general procedure for the introduction of aryl and vinyl substituents in the 5 or 7 position of 8-hydroxyquinoline has been developed. The methodology presented is based upon the Suzuki cross-coupling reaction of aryl or vinyl halide