5332-24-1

Usage

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

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)

Upstream product

• 91-22-5 quinoline 
• 36825-36-2 3-bromo-quinolin-4-ylamine 
• 530-64-3 quinoline hydrochloride 
• 141812-98-8 1-benzoyl-3-bromo-2-cyano-1,2,3,4-tetrahydro-4-methoxyquinoline 
• 22615-00-5 3-bromoquinoline N-oxide 
• 7664-93-9 sulfuric acid 
• 7726-95-6 bromine 
• 7732-18-5 water 
• 580-17-6 3-aminoquinoline 
• 13721-17-0 1-benzoyl-1,2-dihydro-quinoline-2-carbonitrile 
• 578-68-7 4-aminoquinoline 
• 102941-76-4 3-bromoquinoline-borane 
• 6480-68-8 quinoline-3-carboxylic acid 
• 2065-75-0 2-Bromo-malonaldehyde 

Downstream Products

• 91-22-5 quinoline 
• 77492-62-7 2-adamantan-1-yl-quinoline 
• 78509-34-9 6-(1-Adamantyl)-5,6-dihydrochinolin 
• 78509-30-5 7-(1-Adamantyl)-chinolin 
• 77492-63-8 7-(1-adamantyl)-7,8-dihydroquinoline 
• 25199-76-2 3-(trifluoromethyl)quinoline 
• 87393-53-1 3-phenylsulfanyl-quinoline 
• 34846-64-5 3-cyanoquinoline 
• 65094-36-2 3-(Trimethylsilylmethyl)chinolin 
• 37045-14-0 phenyl(quinolin-3-yl)methanone 
• 112170-36-2 α-phenyl-3-quinolylacetonitrile 
• 112177-31-8 4-(3-quinolyl)phenylacetonitrile 
• 112177-30-7 2-(3-quinolyl)phenylacetonitrile 
• 130138-42-0 Benzenesulfonyl-quinolin-3-yl-acetonitrile 

Relevant academic research and scientific papers

Synthesis method of 3-bromoquinoline compound

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-Photosensitized Aryl and Alkyl Decarboxylative Functionalization Reactions

Despite significant progress in aliphatic decarboxylation, an efficient and general protocol for radical aromatic decarboxylation has lagged far behind. Herein, we describe a general strategy for rapid access to both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters followed by their successive use in divergent carbon–heteroatom and carbon–carbon bond-forming reactions. Identification of a suitable activator for carboxylic acids is the key to bypass a competing single-electron-transfer mechanism and “switch on” an energy-transfer-mediated homolysis of unsymmetrical σ-bonds for a concerted fragmentation/decarboxylation process.

Visible-Light Photocatalyzed Deoxygenation of N-Heterocyclic N-Oxides

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.

Actinide-Based Porphyrinic MOF as a Dehydrogenation Catalyst

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

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

CONDENSED-CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DIODE INCLUDING THE CONDENSED-CYCLIC COMPOUND

A condensed-cyclic compound and an organic light-emitting diode including the condensed-cyclic compound.

Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylisulfonium halides generated in situ

Halodimethylsulfonium halide 1, which is readily formed in situ from hydrohaloic acid and DMSO, is a good nucleophilic halide. This activated nucleophilic halide rapidly converts aryldiazonium salt prepared in situ by the same hydrohaloic acid and nitrite ion to aryl chlorides, bromides, or iodides in good yield. The combined action of nitrite ion and hydrohaloic acid in DMSO is required for the direct transformation of aromatic amines, which results in the production of aryl halides within 1 h. Substituted compounds with electron-donating or -withdrawing groups or sterically hindered aromatic amines are also smoothly transformed to the corresponding aromatic halides. The only observed by-product is the deaminated arene (usually 7%). The isolated aryldiazonium salts can also be converted to the corresponding aryl halides using 1. The present method offers a facile, one-step procedure for transforming aminoarenes to haloarenes and lacks the environmental pollutants that usually accompany the Sandmeyer reaction using copper halides.

Microbial deoxygenation of N-oxides with Baker's yeast-NaOH

The microbial deoxygenation of a series of aromatic and heteroaromatic N-oxide compounds, including quinoline N-oxides, isoquinoline N-oxides, 2-aryl-2H-benzotriazole 1-oxides, benzo[c]cinnoline N-oxide and azoxybenzenes, has been performed with bakers'yeast-NaOH.

1,3-dibromo-5,5-dimethylhydantoin, a useful reagent for aromatic bromination

1,3-dibromo-5,5-dimethylhydantoin (DBDMH) is a useful and easy to handle reagent for bromination of various aromatic derivatives substituted with electron donating groups. In the presence of trimethylsilyltrifluoromethanesulfonate, DBDMH showed increased reactivity, and in one case, the reaction followed another pathway, suggesting an alternative mechanism.

Bipyridyls and their use as inks

Process employing bipyridyls as inks, of the general formula STR1 in which R, R' are, for example, alkyl and R1, R2, R3, R4, R5, R6 are, for example hydrogen or alkyl radicals, or R1 and R2 or R2 and R3, and/or R4 and R5 or R5 and R6 together with the pyridine ring form in isoquinoline or quinoline ring system.