5332-24-1 Usage
Description
3-Bromoquinoline is an organic compound with the chemical formula C9H6BrN and is a derivative of quinoline, featuring a bromine atom at the 3rd position. It is a colorless to light yellow liquid and is known for undergoing bromine-magnesium exchange reactions, which allows for the synthesis of various functionalized quinolines.
Uses
Used in Pharmaceutical Industry:
3-Bromoquinoline is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable building block in the development of new drugs.
Used in Pesticide Industry:
3-Bromoquinoline is also utilized as an intermediate in the production of certain pesticides. Its chemical properties contribute to the effectiveness of these agricultural chemicals in controlling pests and protecting crops.
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
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
-
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.
Actinide-Based Porphyrinic MOF as a Dehydrogenation Catalyst
Hu, Kong-Qiu,Huang, Zhi-Wei,Zhang, Zhi-Hui,Mei, Lei,Qian, Bing-Bing,Yu, Ji-Pan,Chai, Zhi-Fang,Shi, Wei-Qun
supporting information, p. 16766 - 16769 (2018/10/31)
Uranyl–organic frameworks (UOFs) have recently been the object of many research endeavors due to the unique coordination mode of uranyl ions and their attractive physicochemical properties. Here, a new (3,4)-connected UOF (U-IHEP-4) assembled from uranyl and porphyrin ligand tetrakis(4-carboxyphenyl)porphyrin (H4TCPP) is reported, which represents the first case of actinide porphyrinic MOFs. Adsorption experiments in DMF solution demonstrated that U-IHEP-4 selectively adsorbs positively charged dyes, which is in line with its negatively charged framework and large pore volume ratio (90 %). Remarkably, U-IHEP-4 exhibited high catalytic activity for the dehydrogenation of N-heterocycles to synthesize the corresponding aromatic heterocycles and it can be used as an efficient heterogeneous catalyst.
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
