65550-77-8

Basic information

• Product Name: 2-Bromo-3-methyl-5-chloropyridine
• Synonyms: 2-CHLORO-5-BROMO-3-PICOLINE;2-BROMO-5-CHLORO-3-PICOLINE;5-BROMO-2-CHLORO-3-METHYLPYRIDINE;2-bromo-3-methyl-5-chloropyridine;2-BROMO-5-CHLORO-3-METHYLPYRIDINE;2-BROMO-3-METHYL-5-CHLOROPURIDINE;6-Bromo-5-chloro-3-picoline;Bromo chloro picoline
• CAS NO: 65550-77-8
• Molecular Formula: C₆H₅BrClN
• Molecular Weight: 206.47
• Product Categories: Pyridine;Pyridines;Boronic Acid;Pyridine Series;Heterocycle-Pyridine series
• Mol File: 65550-77-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 40-44 °C
• Boiling Point: 240.3 °C at 760 mmHg
• Flash Point: 99.1 °C
• Appearance: /
• Density: 1.624
• Vapor Pressure: 0.0593mmHg at 25°C
• Refractive Index: 1.571
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: soluble in Methanol
• PKA: -1.20±0.20(Predicted)
• CAS DataBase Reference: 2-Bromo-3-methyl-5-chloropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-3-methyl-5-chloropyridine(65550-77-8)
• EPA Substance Registry System: 2-Bromo-3-methyl-5-chloropyridine(65550-77-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 37/39-26-39
• Hazardous Substances Data: 65550-77-8(Hazardous Substances Data)

Usage

General Description

2-Bromo-3-methyl-5-chloropyridine is a chemical compound with the molecular formula C6H5BrClN. It is a heterocyclic compound, which contains a pyridine ring with bromine, methyl, and chlorine substituents. 2-Bromo-3-methyl-5-chloropyridine is used as a building block in organic synthesis, particularly in the pharmaceutical industry for the production of various pharmaceuticals, agrochemicals, and other fine chemicals. It has also been studied for its potential use in the development of new drug candidates. Additionally, 2-Bromo-3-methyl-5-chloropyridine is known for its reactivity and is used in a variety of chemical reactions to introduce the pyridine ring into various organic molecules.

InChI:InChI=1/C6H5BrClN/c1-4-2-5(8)3-9-6(4)7/h2-3H,1H3

Synthetic route

3-methylpyridin-2-ylamine (1603-40-3) → 2-bromine-3-methyl-5-chloropyridine (65550-77-8)

Conditions	Yield
With hydrogen bromide; bromine; sodium nitrite 1.) chlorination; 2.) water, -10 deg C, 1.5 h, 0 deg C, 0.5 h; Multistep reaction;

2-bromine-3-methyl-5-chloropyridine (65550-77-8) + 2-methylpyridine-4-boronic acid (579476-63-4) → 5-chloro-2',3-dimethyl-2,4'-bipyridine

Conditions	Yield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); triethylamine In water; acetone at 20℃; for 4h; Solvent; Temperature; Suzuki Coupling;	100%

2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (660867-80-1) + 2-bromine-3-methyl-5-chloropyridine (65550-77-8) → 5-chloro-2',3-dimethyl-2,4'-bipyridine

Conditions	Yield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); TPGS-750-M; triethylamine In water; acetone at 45℃; for 31h; Solvent; Suzuki-Miyaura Coupling; Inert atmosphere;	85%

2-bromine-3-methyl-5-chloropyridine (65550-77-8) + Trimethylenediamine (109-76-2) → N-(5-chloro-3-methyl-2-pyridyl)-1,3-diaminopropane (92992-77-3) + N,N'-Bis-(5-chloro-3-methyl-pyridin-2-yl)-propane-1,3-diamine

Conditions	Yield
In pyridine for 3.5h;	A 76% B n/a

zinc(II) cyanide (557-21-1) + tris-(dibenzylideneacetone)dipalladium(0) (52409-22-0, 51364-51-3) + 2-bromine-3-methyl-5-chloropyridine (65550-77-8) → 5-chloro-3-methylpyridine-2-carbonitrile (156072-84-3)

Conditions	Yield
	76%

zinc(II) cyanide (557-21-1) + 2-bromine-3-methyl-5-chloropyridine (65550-77-8) → 5-chloro-3-methylpyridine-2-carbonitrile (156072-84-3)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In N,N-dimethyl acetamide at 110℃; for 4h;	76%
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In N,N-dimethyl acetamide at 110℃; for 4h;	76%
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In N,N-dimethyl acetamide at 110℃; for 4h;	76%

2-bromine-3-methyl-5-chloropyridine (65550-77-8) + ethylenediamine (107-15-3) → 2-(2-aminoethylamino)-5-chloro-3-methylpyridine (92992-98-8) + N,N'-Bis-(5-chloro-3-methyl-pyridin-2-yl)-ethane-1,2-diamine

Conditions	Yield
In pyridine for 6.5h; Heating;	A 73% B n/a

1-methyl-piperazine (109-01-3) + 2-bromine-3-methyl-5-chloropyridine (65550-77-8) → 1-(5-chloro-3-methyl-2-pyridyl)-4-methylpiperazine

Conditions	Yield
With dichloro[4,5-bis(diphenylphosphino)-9,9’-dimethylxanthene]palladium(II); sodium t-butanolate at 75℃; Buchwald-Hartwig Coupling; Inert atmosphere;	73%

2-bromine-3-methyl-5-chloropyridine (65550-77-8) + 1,4-diaminobutane (110-60-1) → 2-(4-aminobutylamino)-5-chloro-3-methylpyridine (92993-00-5) + N,N'-Bis-(5-chloro-3-methyl-pyridin-2-yl)-butane-1,4-diamine

Conditions	Yield
In pyridine for 4h; Heating;	A 72% B n/a

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → 2-[2-(5-chloro-3-methylpyrid-2-ylamino)ethylamino]-5-(6-methylpyrid-3-ylmethyl)-4-pyrimidone (92992-99-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / pyridine / 6.5 h / Heating 2: 86 percent / pyridine / 22 h / Heating View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → 2-<3-(5-chloro-3-methyl-2-pyridylamino)propylamino>-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone (92992-78-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / pyridine / 3.5 h 2: 83 percent / pyridine / 22 h / Heating View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → 2-[4-(5-chloro-3-methylpyrid-2-ylamino)butylamino]-5-(6-methylpyrid-3-ylmethyl)-4-pyrimidone (92993-01-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / pyridine / 4 h / Heating 2: 39 percent / 5 h / 140 °C View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) + ethanol (64-17-5) → 2-bromo-5-ethoxy-3-methylpyridine (1509949-25-0)

Conditions	Yield
Stage #1: ethanol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 2-bromine-3-methyl-5-chloropyridine In N,N-dimethyl-formamide at 20℃;

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → N-(3-((4S,6S)-2-benzamido-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloro-3-methylpicolinamide

Conditions	Yield
Multi-step reaction with 3 steps 2: ethanol 3: N-ethyl-N,N-diisopropylamine / ethyl acetate View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → N-(3-((4SR,6SR)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloro-3-methyl-2-pyridinecarboxamide

Conditions	Yield
Multi-step reaction with 4 steps 2: ethanol 3: N-ethyl-N,N-diisopropylamine / ethyl acetate 4: ammonia / methanol; dichloromethane View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → N-(5-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-6-fluoropyridin-3-yl)-5-chloro-3-methylpicolinamide (1624603-63-9)

Conditions	Yield
Multi-step reaction with 4 steps 2: ethanol View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → 5-chloro-3-methylpicolinamide (1256790-98-3)

Conditions	Yield
Multi-step reaction with 3 steps 2: ethanol View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloro-3-methylpyridine-2-carbothioamide (1624603-92-4)

Conditions	Yield
Multi-step reaction with 4 steps 2: ethanol 4: ethyl acetate; toluene View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloro-3-methyl-2-pyridinecarboxamide (1624603-18-4)

Conditions	Yield
Multi-step reaction with 3 steps 2: ethanol View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → 5-chloro-3-methylpyridine-2-carboxylic acid (886365-46-4)

Conditions	Yield
Multi-step reaction with 2 steps 2: ethanol View Scheme
Multi-step reaction with 2 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl acetamide / 4 h / 110 °C 2.1: sodium hydroxide / ethanol / 18 h / 90 °C 2.2: pH 4 View Scheme
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl acetamide / 4 h / 110 °C 2: sodium hydroxide / ethanol / 18 h / 90 °C View Scheme
Multi-step reaction with 2 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl acetamide / 4 h / 110 °C 2.1: sodium hydroxide / ethanol / 18 h / 90 °C 2.2: pH 4 View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4,5-difluorophenyl)-5-chloro-3-methylpicolinamide (1624604-70-1)

Conditions	Yield
Multi-step reaction with 3 steps 2: ethanol View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → N-(3-((1S,2R,5R)-4-amino-2,5-dimethyl-8,8-dioxido-8-thia-3-azabicyclo[3.2.1]oct-3-en-2-yl)-4-fluorophenyl)-5-chloro-3-methyl-2-pyridinecarboxamide

Conditions

Yield

Multi-step reaction with 4 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl acetamide / 4 h / 110 °C 2: sodium hydroxide / ethanol / 18 h / 90 °C 3: pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → N-(3-((1S,2R,5R)-4-amino-1,2,5-trimethyl-8,8-dioxido-8-thia-3-azabicyclo[3.2.1]oct-3-en-2-yl)-4-fluorophenyl)-5-chloro-3-methyl-2-pyridinecarboxamide

Conditions

Yield

Multi-step reaction with 4 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl acetamide / 4 h / 110 °C 2: sodium hydroxide / ethanol / 18 h / 90 °C 3: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 1.5 h / 20 °C 4: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → N-(3-((1R,2R,5S)-4-amino-1,2,5-trimethyl-8,8-dioxido-8-thia-3-azabicyclo[3.2.1]oct-3-en-2-yl)-4-fluorophenyl)-5-chloro-3-methyl-2-pyridinecarboxamide

Conditions

Yield

Multi-step reaction with 4 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl acetamide / 4 h / 110 °C 2: sodium hydroxide / ethanol / 18 h / 90 °C 3: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 1.5 h / 20 °C 4: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → C32H40ClFN4O7S

Conditions	Yield
Multi-step reaction with 3 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl acetamide / 4 h / 110 °C 2: sodium hydroxide / ethanol / 18 h / 90 °C 3: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 1.5 h / 20 °C View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → C32H40ClFN4O7S

Conditions	Yield
Multi-step reaction with 3 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl acetamide / 4 h / 110 °C 2: sodium hydroxide / ethanol / 18 h / 90 °C 3: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 1.5 h / 20 °C View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → C31H36ClF2N3O8S

Conditions	Yield
Multi-step reaction with 3 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl acetamide / 4 h / 110 °C 2: sodium hydroxide / ethanol / 18 h / 90 °C 3: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / tetrahydrofuran; methanol / 0.17 h View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) → C31H38ClFN4O7S

Conditions	Yield
Multi-step reaction with 3 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl acetamide / 4 h / 110 °C 2: sodium hydroxide / ethanol / 18 h / 90 °C 3: pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C View Scheme

2-bromine-3-methyl-5-chloropyridine (65550-77-8) + 3-oxo-piperidine-1-carboxylic acid tert-butyl ester (98977-36-7) → tert-butyl 3-(5-chloro-3-methylpyridin-2-yl)-3-hydroxypiperidine-1-carboxylate

Conditions	Yield
Stage #1: 2-bromine-3-methyl-5-chloropyridine With n-butyllithium In diethyl ether; hexane at -70℃; for 1.83333h; Inert atmosphere; Stage #2: 3-oxo-piperidine-1-carboxylic acid tert-butyl ester In diethyl ether; hexane at -70 - 20℃;

Upstream product

• 1603-40-3 3-methylpyridin-2-ylamine 

Downstream Products

• 156072-84-3 5-chloro-3-methylpyridine-2-carbonitrile 
• 1624604-70-1 N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4,5-difluorophenyl)-5-chloro-3-methylpicolinamide 
• 886365-46-4 5-chloro-3-methylpyridine-2-carboxylic acid 
• 1624603-18-4 N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloro-3-methyl-2-pyridinecarboxamide 
• 1624603-92-4 N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloro-3-methylpyridine-2-carbothioamide 

Relevant articles and documents

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