3-Bromoquinoline

Bromoquinoline

There are seven position isomers with the main properties are as follows: ▼▲ Name Melting point(℃) Boiling point(℃) Solubility 2-bromoquinoline 48～49 It is soluble in diethyl ether, chloroform and benzene 3-bromoquinoline 12～15 274～276, 95(66.66Pa) 4-bromoquinoline 29～30 270(decomposition) Easily soluble in dilute acid 5-bromoquinoline 52 (needle crystal) 280 6-bromoquinoline 24 278 7-bromoquinoline 52 (needle crystal) 290 8-bromoquinoline 80 165～166 (2399.79Pa)

Application and synthesis method

3-Bromoquinoline can have action with mixed acid to generate 3-bromo-5-nitroquinoline, followed by heating with potassium permanganate to be oxidized to 5-bromo-2, 3-pyridine dicarboxylic acid. 6-bromo-quinoline can be heated together nitric acid to generate 6-bromo-8-nitro-quinoline, followed by reaction with potassium permanganate to be oxidized into 2, 3-pyridinedicarboxylic acid. 2-bromo-quinoline can be manufactured through the reaction between 2-hydroxyquinoline and phosphorus pentabromide 3-bromo-quinoline can be obtained through heating the quinoline perbromide at 180 ° C. 4-bromoquinoline can be obtained through either the heating reaction between 4-hydroxyquinoline and phosphorus pentabromide or by the diazotization reaction of 4-aminoquinoline. 5-bromo-quinoline can be obtained from the heating reaction between m-bromo aniline, glycerol, m-bromonitrobenzene and concentrated sulfuric acid, or through the diazotization reaction of 5-amino-quinoline. 6-bromo-quinoline can be obtained through the heating reaction between p-bromoaniline, glycerol, concentrated sulfuric acid and p-bromo-nitrobenzene. 7-bromoquinoline can be obtained through the diazotization of 7-aminoquinoline. 8-bromo-quinoline can be obtained through the heating of o-bromo aniline, glycerol, concentrated sulfuric acid and o-bromo-nitrobenzene in the heating system. Purposes: as organic synthesis reagents.

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 1318, 1962 DOI: 10.1021/jo01051a047

Flammability and Explosibility

Notclassified

General Description

3-Bromoquinoline undergoes bromine-magnesium exchange reaction with lithium tributylmagnesate in toluene at -10°C, which is quenched by various electrophiles to yield functionalized quinolines.