137628-17-2

Basic information

• Product Name: 2,3 DIBROMO-5-CHLORO PYRIDINE
• Synonyms: 2,3-DibroMo-5-chloropyridine, 97+%;2,3 DIBROMO-5-CHLORO PYRIDINE;5-CHLORO-2,3-DIBROMOPYRIDINE;2,3-DIBROMO-5-DICHLOROPYRIDINE;Pyridine2,3-dibromo-5-chloropyridine
• CAS NO: 137628-17-2
• Molecular Formula: C₅H₂Br₂ClN
• Molecular Weight: 271.33708
• Product Categories: Heterocycle-Pyridine series;Halides;Pyridines;Pyridine;Variety of halogenated heterocyclic series
• Mol File: 137628-17-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 41.0 to 45.0 °C
• Boiling Point: 259.933 °C at 760 mmHg
• Flash Point: 111.004 °C
• Appearance: /
• Density: 2.137 g/cm³
• Vapor Pressure: 0.02mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• PKA: -3.85±0.20(Predicted)
• CAS DataBase Reference: 2,3 DIBROMO-5-CHLORO PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3 DIBROMO-5-CHLORO PYRIDINE(137628-17-2)
• EPA Substance Registry System: 2,3 DIBROMO-5-CHLORO PYRIDINE(137628-17-2)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-25
• Safety Statements: 26-37-45
• RIDADR: UN 2811 6.1 / PGIII
• HazardClass: IRRITANT
• Hazardous Substances Data: 137628-17-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,3 Dibromo-5-chloro pyridine is used as a reactant for regiospecific Grignard reactions with lactones. The presence of multiple halogens on the pyridine ring allows for selective reactions with Grignard reagents, which are organomagnesium compounds. This selective reactivity is valuable in the synthesis of complex organic molecules and pharmaceutical compounds, as it enables chemists to control the position of functional groups within the molecule.
In the pharmaceutical industry, 2,3 Dibromo-5-chloro pyridine can be used as a building block for the development of new drugs, particularly those targeting the central nervous system or exhibiting antimicrobial properties. The compound's unique structure and reactivity make it a versatile starting material for the synthesis of various drug candidates.
Additionally, 2,3 Dibromo-5-chloro pyridine may find applications in the agrochemical industry, where it can be used as a precursor for the synthesis of pesticides or other crop protection agents. The compound's halogenated nature and reactivity with Grignard reagents can be exploited to create new molecules with improved biological activity and selectivity.

InChI:InChI=1/C5H2Br2ClN/c6-4-1-3(8)2-9-5(4)7/h1-2H

Upstream product

• 137628-16-1 3-bromo-5-chloro-2-hydroxypyridine 
• 26163-03-1 2-amino-3-bromo-5-chloropyridine 
• 137628-16-1 3-bromo-5-chloro-1H-2-pyridone 
• 7440-44-0 pyrographite 
• 7789-59-5 phosphorus(V) oxybromide 

Downstream Products

• 73583-39-8 3-bromo-5-chloropyridine 
• 823221-97-2 3-bromo-5-chloro-2-iodopyridine 
• 914358-72-8 5-bromo-3-chloro-2-methylpyridine 
• 1227605-52-8 2-bromo-5-chloronicotinaldehyde 
• 1393575-76-2 3-chloro-1,7-naphthyridin-8(7H)-one 
• 1260672-65-8 3,8-dichloro-1,7-naphthyridine 
• 1646178-28-0 (S)-3-chloro-1'-phenyl-5,7-dihydrospiro[cyclopenta[b]pyridin]-2'-one 
• 1646178-21-3 C₂₁H₁₆Cl₂N₂O 
• 1646178-60-0 3-((5-chloro-3-(hydroxymethyl)pyridin-2-yl)methyl)-1-phenylindolin-2-one 
• 1375541-21-1 (S)-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-3-carboxylic acid 
• 1374248-80-2 (S)-N-((3S,5S,6R)-6-methyl-2-oxo-5-(o-tolyl)-1-(2,2,2-trifluoroethyl)piperidin-3-yl)-2’-oxo-l‘,2’,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3’-pyrrolo[2,3-b]pyridine]-3-carboxamide 
• 1374248-83-5 (S)-N-((3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)piperidin-3-yl)-2’-oxo-1‘,2’,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3‘-pyrrolo [2,3-b]pyridine]-3-carboxamide 
• 202409-33-4 etoricoxib 
• 1227588-49-9 3-bromo-5-chloropyridine-2-carbaldehyde 

Relevant articles and documents

Chiral Hexahalogenated 4,4′-Bipyridines

The preparation of 27 isomers of chiral hexahalogeno-4,4′-bipyridines by means of two complementary methods is described. The first one is convergent and based on the LDA-induced 4,4′-dimerization of trihalopyridines, whereas the second method is divergent and achieved through regioselective halogenation reactions of 4,4′-bipyridine-2,2′-diones. Iodine in 2,2′-positions of the 4,4′-bipyridines was introduced by a copper-catalyzed Finkelstein reaction (Buchwald procedure) performed on 2,2′-dibromo derivatives. Selected compounds of this new family of atropisomeric 4,4′-bipyridines were enantioseparated by high performance liquid chromatography on chiral stationary phases, and the absolute configurations of the separated enantiomers were assigned by using X-ray diffraction analysis. The latter revealed that various halogen bond types are responsible for crystal cohesion.

Logistic flexibility in the preparation of isomeric halopyridinecarboxylic acids

Although there are many conceivable ways to funtionalize, and specifically carboxylate, 2-chloro-4-(trifluoromethyl)pyridine optionally at all three vacant positions, it is more straightforward to prepare only the 2-chloro-4- (trifluoromethyl)pyridine-3-carboxylic acid (1) from this precursor and the other 6-chloro-4-(trifluoromethyl)pyridine-2- and -3-carboxylic acids (2 and 3) from a different one, viz. 5-bromo-2-chloro-4-(trifluoromethyl)pyridine. In the same manner, it proved more convenient to convert 5-chloro-2-(trifluoromethyl) pyridine in only two of the corresponding acids (6 and 7) and to make the third one (8) from 3-bromo-5-chloro-2-(trifluoromethyl)pyridine as an alternative starting material. All model substrates for functionalization were readily accessible from the correspondingly substituted chloroiodopyridine through heavy halogen displacement by in situ generated (trifluoromethyl)copper. Graphical Abstract

3-bromo-5-chloro-pyridines used as intermediates in the synthesis of azatetralones

Compounds of the formula STR1 wherein R1 is hydrogen, fluoro, chloro, bromo, nitro, trifluoromethyl, C1 to C4 alkoxy, C1 to C4 alkylthio or C1 to C6 alkyl and R2 is a group of the formula STR2 wherein R3 is hydrogen or C1 to C6 alkyl, R4 is --CH=C2, --CH2 --YR5, or --COR6, R5 is hydrogen or an acid labile alcohol protecting group, Y is oxygen or sulfur, and R6 is --NR7 R8 or --OR9 wherein R7, R8 and R9 are independently selected from hydrogen or C1 to C6 alkyl, or an alkaline or alkaline earth metal salt thereof, which are intermediates in the preparation of hydantoin aldose reductase inhibitors and methods of preparing these intermediates.

6-CHLORO-3,4-DIHYDRO-PYRANO [2,3-B]PYRIDINES HAVING THE R CONFIGURATION

The present invention relates to processes and intermediates for the preparation of spiro-heteroazolones. The latter compounds are useful as aldose reductase inhibitors