52200-48-3

Basic information

• Product Name: 3-Bromo-2-chloropyridine
• Synonyms: 3-Bromo-2-chlorolpyridine;3-BROMO-2-CHLOROPYRIDINE 98+%;3-broMo -2-chlorine pyridine;2 - chloro - 3 - broMide pyridine;52200-48-3;3-Bromo-2-chloropyridine 98%;TIMTEC-BB SBB003618;OTAVA-BB BB7110952626
• CAS NO: 52200-48-3
• Molecular Formula: C₅H₃BrClN
• Molecular Weight: 192.44102
• EINECS: -0
• Product Categories: compounds of pyridine;blocks;Bromides;Pyridines;Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;Halides;Pyridine series;Bromopyridines;Chloropyridines;Halopyridines;Boronic Acid;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Variety of halogenated heterocyclic series;alkyl chloride| alkyl bromide
• Mol File: 52200-48-3.mol

Chemical Properties

• Melting Point: 54-57 °C(lit.)
• Boiling Point: 97 °C / 10mmHg
• Flash Point: 86.8 °C
• Appearance: White to yellow/Crystalline Powder, Crystals or Flakes or Solid
• Density: 1.7783 (rough estimate)
• Vapor Pressure: 0.173mmHg at 25°C
• Refractive Index: 1.5400 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -0.63±0.10(Predicted)
• BRN: 109812
• CAS DataBase Reference: 3-Bromo-2-chloropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-2-chloropyridine(52200-48-3)
• EPA Substance Registry System: 3-Bromo-2-chloropyridine(52200-48-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 52200-48-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-2-chloropyridine is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its application reason is due to its unique chemical structure, which allows for the creation of a range of molecules with potential therapeutic properties.
Used in Chemical Synthesis:
3-Bromo-2-chloropyridine is used as a building block in the synthesis of complex organic molecules. It serves as a key component in the production of various compounds, such as:
1. Acetylenic dipyridone: 3-Bromo-2-chloropyridine is used as a starting material for the synthesis of acetylenic dipyridone, which may have potential applications in medicinal chemistry.
2. 3-Ethynyl-2-(phenylmethoxy)-pyridine: 3-Bromo-2-chloropyridine is synthesized using 3-bromo-2-chloropyridine and is potentially useful in the development of new pharmaceutical agents.
3. Nemertelline: 3-Bromo-2-chloropyridine is utilized in the synthesis of nemertelline, a compound that may have biological activities of interest.
4. Ortho-chlorodiheteroarylamine: 3-Bromo-2-chloropyridine is synthesized from 3-bromo-2-chloropyridine and is used in the development of new chemical entities with potential applications in various fields.
5. 2-Chloro-N-(2,3,7-trimethylbenzo[b]thien-6-yl)pyridin-3-amine: 3-Bromo-2-chloropyridine is used in the synthesis of this compound, which may have potential applications in the pharmaceutical industry.

InChI:InChI=1/C5H3BrClN/c6-4-2-1-3-8-5(4)7/h1-3H

Upstream product

• 109-09-1 2-chloropyridine 
• 2402-97-3 3-bromopyridine N-oxide 
• 13472-59-8 3-Bromo-2-methoxypyridine 
• 6298-19-7 2-chloro-3-aminopyridine 
• 52200-49-4 3-bromo-2-(phenylmethoxy)pyridine 
• 7791-25-5 sulfuryl dichloride 
• 77332-76-4 2-chloro-3-(trimethylsilyl)pyridine 
• 13534-89-9 2,3-dibromopyridine 
• 2942-59-8 2-chloronicotinic acid 
• 30683-23-9 3-bromopicolinic acid 
• 13466-43-8 3-bromo-pyridin-2-ol 

Downstream Products

• 87394-56-7 1-(3-bromo-2-pyridyl)piperazine 
• 87394-59-0 3-Brom-2-(4-methyl-1-piperazinyl)pyridin 
• 109-09-1 2-chloropyridine 
• 73589-41-0 chloro-2 bromo-4 butyl-3 pyridine 
• 109-04-6 2-bromo-pyridine 
• 100921-62-8 bromo-4 chloro-2 deuterio-3 pyridine 
• 73583-36-5 chloro-2 butyl-3 pyridine 
• 100921-61-7 chloro-2 deuterio-3 pyridine 
• 100921-63-9 chloro-2 butyl-4 pyridine 
• 128071-88-5 bromo-4 chloro-2 (hydroxy-1 ethyl)-3 pyridine 
• 128071-84-1 bromo-4 chloro-2 formyl-3 pyridine 
• 96592-19-7 3-Bromo-2-(1-methyl-1H-imidazol-2-ylsulfanyl)-pyridine 
• 128071-86-3 bromo-4 chloro-2 methyl-3 pyridine 
• 73583-38-7 bromo-4 chloro-2 (chloro-2' pyridyl-4')-3 pyridine 

Relevant articles and documents

Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions

A convenient and efficient method for the synthesis of 2-halogen-substituted pyridines is described. The decarboxylative halogenation of 2-picolinic acids with dihalomethane proceeded smoothly via N-chlorocarbene intermediates to afford 2-halogen-substituted pyridines in satisfactory to excellent yields under transition-metal-free conditions. This new type of decarboxylative halogenation is operationally simple and exhibits high functional-group tolerance.

PROCESS FOR PREPARING A COMPOUND BY A NOVEL SANDMEYER-LIKE REACTION USING A NITROXIDE RADICAL COMPOUND AS A REACTION CATALYST

The present invention provides a novel process for preparing a substituted aromatic compound such as an aromatic halo compound or a salt thereof through a transformation reaction of an aromatic diazonium salt from an aromatic amino compound at stable high yields utilizing a novel Sandmeyer-like reaction using a nitroxide radical compound as a reaction catalyst.

Large-scale solvent-free chlorination of hydroxy-pyrimidines,-pyridines,- pyrazines and-amides using equimolar POCl3

Chlorination with equimolar POCl3 can be efficiently achieved not only for hydroxypyrimidines, but also for many other substrates such as 2-hydroxy-pyridines,-quinoxalines, or even-amides. The procedure is solvent-free and involves heating in a sealed reactor at high temperatures using one equivalent of pyridine as base. It is suitable for large scale (multigram) batch preparations.

A novel mode of reactivity for gold(I): The decarboxylative activation of (hetero)aromatic carboxylic acids

Gold(I) salts are found to mediate the decarboxylation of a variety of aromatic and heteroaromatic carboxylic acids at significatively lower temperatures (as low as 60°C) than the currently used copper(I) (180-190°C) and silver(I) (80-140°C) systems. In contrast to silver(I)- and copper(I)-mediated decarboxylations, the resulting aryl-gold(I) complexes are stable towards protodemetallation and can be readily isolated.

Bromine-lithium exchange under non-cryogenic conditions: TMSCH 2Li-LiDMAE promoted C-2 lithiation of 2,3-dibromopyridine

The first C-2 selective bromine-lithium exchange in 2,3-dibromopyridine was performed at 0°C in toluene using the TMSCH2Li-LiDMAE reagent. The Royal Society of Chemistry.

Recommendable routes to trifluoromethyl-substituted pyridine- and quinolinecarboxylic acids

As part of a case study, rational strategies for the preparation of all ten 2-, 3-, or 4-pyridinecarboxylic acids and all nine 2-, 3-, 4-, or 8-quinolinecarboxylic acids bearing trifluoromethyl substituents at the 2-, 3-, or 4-position were elaborated. The trifluoromethyl group, if not already present in the precursor, was introduced either by the deoxygenative fluorination of suitable carboxylic acids with sulfur tetrafluoride or by the displacement of ring-bound bromine or iodine by trifluoromethylcopper generated in situ. The carboxy function was produced by treatment of organolithium or organomagnesium intermediates, products of halogen/metal or hydrogen/ metal permutation, with carbon dioxide. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

Substituent Effect on the Chlorination of 2-Alkoxypyridines to give 2-Chloropyridines under Vilsmeier-Haack Conditions

Various substituted 2-alkoxypyridines were converted into the corresponding 2-chloropyridines in 28-91% yields by use of POCl3 and DMF, in which the methyl, halogen, ester and nitro groups displayed an activating effect; in contrast, an amino group exhibited a deactivating effect.

Use of Hydrogen Bonds To Control Molecular Aggregation. Behavior of Dipyridones and Pyridone-Pyrimidones Designed To Form Cyclic Triplexes

The tendency of 2-pyridones and related heterocycles to form cyclic hydrogen-bonded dimers allows them to be used as sticky sites that induce molecules in which they are incorporated to associate in particular ways.Compound 7, which is constructed from pyridone and pyrimidone subunits linked to a rigid linear acetylenic spacer, incorporates an array of hydrogen-bonding sites designed to favor the formation of a cyclic triplex.Pyridone-pyrimidone 7 was synthesized and the structure of its DMSO solvate was determined by X-ray crystallography.Aggregation does not produce a cyclic triplex but rather gives chains in which adjacent molecules of compound 7 are linked by single hydrogen bonds.

Le phenyl-lithium: nouvel agent de metallation du cycle pyridinique

Nucleophilic addition was the sole reaction of phenyl-lithium with a pyridinic ring; now the novel catalysed metallation, with phenyl-lithium, of many substituted pyridine compounds giving various derivatives in high yields with many different reagents, has been achieved.

A Convenient Synthesis of Halogenated 2-Chloropyridines by Transformation of Halogenated 2-Methoxypyridines under Vilsmeier-Haack Conditions

Several halogenated 2-chloropyridines 2a-2h were conveniently synthesized by transformation of halogenated 2-methoxypyridines 1a-1h under Vilsmeier-Haack conditions in a yield of 50-71percent.