73583-37-6

Basic information

• Product Name: 2-Chloro-4-bromopyridine
• Synonyms: 2-Chloro-4-boroMopyridine;2 - chloro - 4 - broMide pyridine;PYRIDINE, 4-BROMO-2-CHLORO-;4-BROMO-2-CHLOROPYRIDINE;2-CHLORO-4-BROMOPYRIDINE;4-Bromo-2-chloropyridine 98%;2-chloro-4-bromopyridne;2-CHLORO-4-FLUOROYRIDINE
• CAS NO: 73583-37-6
• Molecular Formula: C₅H₃BrClN
• Molecular Weight: 192.44
• EINECS: -0
• Product Categories: blocks;Bromides;Pyridines;Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;pharmacetical;Pyridine series;Halides;Bromopyridines;Chloropyridines;Halopyridines;Boronic Acid;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Variety of halogenated heterocyclic series
• Mol File: 73583-37-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 27 C
• Boiling Point: 70 °C / 3mmHg
• Flash Point: 225 °F
• Appearance: Yellow/Powder
• Density: 1.7336 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.122mmHg at 25°C
• Refractive Index: n20/D 1.5900(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 0.24±0.10(Predicted)
• Water Solubility: Not miscible or difficult to mix in water.
• CAS DataBase Reference: 2-Chloro-4-bromopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-bromopyridine(73583-37-6)
• EPA Substance Registry System: 2-Chloro-4-bromopyridine(73583-37-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38
• Safety Statements: 26-36-36/37/39-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 73583-37-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-white Cryst

Uses

It is used in the synthesis of quaterpyridine nemertelline.

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

Upstream product

• 14432-12-3 4-Amino-2-chloropyridine 
• 30766-03-1 4-bromo-2-picolinic acid 
• 14432-16-7 2-chloro-4-nitropyridine-N-oxide 
• 2402-95-1 2-chloropyridine-N-oxide 
• 52200-48-3 3-bromo-2-chloropyridine 

Downstream Products

• 128071-84-1 bromo-4 chloro-2 formyl-3 pyridine 
• 1289555-51-6 2-chloro-4-(thiophen-2-yl)pyridine 
• 1375500-72-3 {4-[2-(4-fluoro-phenyl)-pyrrolidin-1-yl]-pyridin-2-yl}-urea 
• 1375502-01-4 4-[2-(4-fluoro-phenyl)-pyrrolidin-1-yl]-pyridin-2-ylamine 
• 1375501-99-7 2-chloro-4-[2-(4-fluoro-phenyl)-pyrrolidin-1-yl]-pyridine 
• 1006052-78-3 8-(2-(benzyloxy)pyridine-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane 
• 1253415-35-8 1-(2-(benzyloxy)pyridine-4-yl)piperidin-4-one 
• 1253410-14-8 C₂₂H₂₄N₆O₃S 
• 458532-84-8 2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine 
• 42260-39-9 2-chloro-4-(phenyl)pyridine 
• 1333467-73-4 N-(4-(4-Fluoro-2-methoxyphenyl)pyridin-2-yl)cyclohexanecarboxamide 
• 1000933-25-4 2-chloropyridine-4-sulfonyl chloride 
• 1268621-57-3 1-(2-fluoro-5-methylphenyl)-3-{4-[2-(1H-pyrrol-2-yl)pyridin-4-yl]phenyl}urea 
• 1268621-54-0 tert-butyl (4-(2-chloropyridin-4-yl)phenyl)carbamate 

Relevant articles and documents

Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis

The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.

Concise Entries to 4-Halo-2-pyridones and 3-Bromo-4-halo-2-pyridones

Methods for the synthesis of both simple 4-halo-2-pyridones and more functionalized 3,4-di- and (3,4,5-tri)-halo-2-pyridones are described that are based on a combination of Sandmeyer and regioselective (copper-mediated) halogenation, with a 2-chloro or a 2-benzyloxy moiety serving as a masked 2-pyridone.

Synthesis of a naphthyridone p38 MAP kinase inhibitor

Compound 1 is a p38 MAP kinase inhibitor potentially useful for the treatment of rheumatoid arthritis and psoriasis. A novel six-step synthesis suitable for large-scale preparation was developed in support of a drug development program at Merck Research Laboratories. The key steps include a tandem Heck-lactamization, N-oxidation, and a highly chemoselective Grignard addition of 4-(N-tert-butylpiperidinyl)-magnesium chloride to a naphthyridone N-oxide. The N-oxide exerted complete chemoselectivity via chelation in directing the Grignard addition to the α position as opposed to 1,4-addition on the enelactam. The dihydropyridyl adduct was in situ aromatized with isobutylchloroformate followed by heating in pyridine. Syntheses of Grignard precursor, N-tert-butyl-4-chloro-piperidine, were accomplished via transamination with a quaternary ammonium piperidone or via addition of methylmagnesium chloride to an iminium ion. Utilizing this chemistry, multi-kilogram preparation of compound 1 was successfully demonstrated. American Chemical Society.