5332-24-1 Usage
Bromoquinoline
There are seven position isomers with the main properties are as follows:
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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.
Uses
For pharmaceuticals
Medicine, pesticide intermediates
Chemical Properties
colorless to light yellow liquid
Synthesis Reference(s)
The Journal of Organic Chemistry, 27, p. 1318, 1962 DOI: 10.1021/jo01051a047
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.
Flammability and Explosibility
Notclassified
Check Digit Verification of cas no
The CAS Registry Mumber 5332-24-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,3,3 and 2 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 5332-24:
(6*5)+(5*3)+(4*3)+(3*2)+(2*2)+(1*4)=71
71 % 10 = 1
So 5332-24-1 is a valid CAS Registry Number.
InChI:InChI=1/C15H12ClN3/c1-9-6-7-12(16)13(8-9)18-15-11-5-3-2-4-10(11)14(17)19-15/h2-8H,1H3,(H2,17,18,19)
5332-24-1Relevant articles and documents
Synthesis method of 3-bromoquinoline compound
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Paragraph 0025; 0028-0031, (2019/07/04)
The invention provides a synthesis method of a 3-bromoquinoline compound. The invention belongs to the field of medical chemical synthesis. The synthesis method comprises the following steps: taking 1, 1, 3, 3-tetramethoxypropane 2 as a raw material to react with bromine to obtain an intermediate 3, obtaining an intermediate 4 from the intermediate 3 under the action of alkali, and reacting the intermediate 4 with a substituted aniline compound to obtain the 3-bromoquinoline compound 1, wherein R1 and R2 are selected from any one of hydrogen, alkyl, alkoxy, halogen, ester, nitro, trifluoromethyl, trifluoromethoxy, dimethylamino, acetyl and methylthio. The synthesis method of the 3-bromoquinoline compound has the advantages of few reaction steps, simplicity in operation, cheap and easily available raw materials, high yield, easiness in purification and easiness in amplified production.
Visible-Light Photocatalyzed Deoxygenation of N-Heterocyclic N-Oxides
Kim, Kyu Dong,Lee, Jun Hee
supporting information, p. 7712 - 7716 (2019/01/03)
A scalable and operationally simple method is described that allows for the chemoselective deoxygenation of a wide range of N-heterocyclic N-oxides (a total of 36 examples). This visible-light-induced protocol features the use of only commercially available reagents, room-temperature conditions, and unprecedented chemoselective removal of the oxygen atom in a quinoline N-oxide in the presence of a pyridine N-oxide in the same molecule through the judicious selection of a photocatalyst.
Copper-catalyzed oxygen atom transfer of N-oxides leading to a facile deoxygenation procedure applicable to both heterocyclic and amine N-oxides
Jeong, Jisu,Lee, Donggun,Chang, Sukbok
supporting information, p. 7035 - 7038 (2015/04/22)
Deoxygenation of various types of N-oxides including both heterocyclic and alkyl(aryl)amine derivatives has successfully been developed by the copper-catalyzed oxygen atom transfer using diazo compounds as the oxygen acceptor. The reaction proceeds smoothly over a broad range of substrates with excellent functional group tolerance under mild conditions. This journal is
