4926-28-7

Basic information

• Product Name: 2-Bromo-4-methylpyridine
• Synonyms: 2-BROMO-4-METHYLPYRIDINE;2-BROMO-4-PICOLINE;RARECHEM AH CK 0041;2-BROMO-4-METHYLPYRIDINE 99%;2-Bromo-4-MythylPyridine;2-BROMO-4-MEFHYL PYRIDINE;-Bromo-4-methylpyridine;2-BROMO-4-METHYLPYRIDINE (2-BROMO-4-PICOLINE)
• CAS NO: 4926-28-7
• Molecular Formula: C₆H₆BrN
• Molecular Weight: 172.02
• EINECS: -0
• Product Categories: compounds of pyridine;Pyridine;pyridine derivative;Pyridine Series;Pyridines, Pyrimidines, Purines and Pteredines;Pyridines;Bromopyridines;Halopyridines;Boronic Acid;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Brominated heterocyclic series;Aromatics;Heterocycles;alkyl bromide
• Mol File: 4926-28-7.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 87 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow/Liquid
• Density: 1.545 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.173mmHg at 25°C
• Refractive Index: n20/D 1.561(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol (Slightly)
• PKA: 1.46±0.10(Predicted)
• BRN: 107331
• CAS DataBase Reference: 2-Bromo-4-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4-methylpyridine(4926-28-7)
• EPA Substance Registry System: 2-Bromo-4-methylpyridine(4926-28-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 4926-28-7(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to orange oily liqui

Uses

2-Bromo-4-methylpyridine may be used:in the total synthesis of ocular age pigment A2-E (2 equiv of retinal (vitamin A) and 1 equiv of ethanolamine)in the preparation of methoxy-2-(2-pyridyl)indolesin the preparation of 2-(2′,4′-difluorophenyl)-4-methylpyridine, via a Suzuki coupling reaction with 2,4-difluorophenylboronic acid

InChI:InChI=1/C6H6BrN/c1-5-2-3-8-6(7)4-5/h2-4H,1H3

Synthetic route

2-Amino-4-methylpyridine (695-34-1) → 2-Bromo-4-picoline (4926-28-7)

Conditions	Yield
With hydrogen bromide; bromine; sodium nitrite In water at 0℃; for 3h;	94%
With sodium hydroxide; hydrogen bromide; bromine; sodium nitrite In water	90%
With hydrogen bromide; bromine; sodium nitrite at 5℃;	87%

picoline (108-89-4) → 2-Bromo-4-picoline (4926-28-7)

Conditions	Yield
Stage #1: picoline With n-butyllithium; 2-(N,N-dimethylamino)ethanol In hexane at 0℃; for 1h; Stage #2: With carbon tetrabromide In tetrahydrofuran; hexane at -78℃; for 1h; Further stages.;	70%

picoline (108-89-4) + acetyl hypofluorite (78948-09-1) → 2-Bromo-4-picoline (4926-28-7) + 4-methylpyridin-2-yl acetate (108168-80-5)

Conditions	Yield
With 1,2-dibromomethane Ambient temperature;	A 55% B n/a

2-hydroksy-4-methyl-pyridine (13466-41-6) + ethyl acetate-water + Bromoform (75-25-2) → 2-Bromo-4-picoline (4926-28-7)

Conditions	Yield
With phosphorus tribromide In water

2-Amino-4-methylpyridine (695-34-1) → 2-Bromo-4-picoline (4926-28-7) + 2-bromo-4-bromomethyl pyridine (83004-14-2)

4-methylpicolinic acid (4021-08-3) → 2-Bromo-4-picoline (4926-28-7)

Conditions	Yield
With tert-butylhypochlorite; dichloromethane; oxygen; sodium hydrogencarbonate at 70℃; for 20h; Green chemistry;	55 %Spectr.

2-Bromo-4-picoline (4926-28-7) + 4'-((2-butyl-4-oxo-8-oxa-1,3-diazaspiro[4.5]dec-1-en-3-yl)methyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-carbonitrile → 4'-((2-butyl-4-oxo-8-oxa-1,3-diazaspiro[4.5]dec-1-en-3-yl)methyl)-5-(4-methylpyridin-2-yl)-[1,1'-biphenyl]-2-carbonitrile

Conditions	Yield
With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In tetrahydrofuran at 120℃; for 0.75h; Inert atmosphere; Sealed tube; Microwave irradiation;	100%

2-Bromo-4-picoline (4926-28-7) + benzyl bromide (100-39-0) → 2-benzyl-4-methyl pyridine (5191-54-8)

Conditions	Yield
With zinc; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Alkylation;	99%

2-Bromo-4-picoline (4926-28-7) + 2-(3-(quinolin-2-yl)phenoxy)-9H-carbazole → 9-(4-methylpyridin-2-yl)-2-(3-(quinolin-2-yl)phenoxy)-9H-carbazole

Conditions	Yield
With 1H-imidazole; copper(l) iodide; potassium carbonate In toluene at 120℃; for 72.41h; Inert atmosphere;	99%

2-Bromo-4-picoline (4926-28-7) + 2-methyl-1-propenylbromide (3017-69-4) → 4-methyl-2-(2-methylprop-1-en-1-yl)pyridine

Conditions	Yield
With potassium fluoride; bis(1,5-cyclooctadiene)nickel (0); N,N-dimethyl acetamide; 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; zinc at 0 - 20℃; for 15h; Schlenk technique; Sealed tube; Inert atmosphere; chemoselective reaction;	99%

2-Bromo-4-picoline (4926-28-7) + 3-Bromophenol (591-20-8) → 2-(3-bromophenoxy)-4-methylpyridine

Conditions	Yield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 105℃; for 48h; Inert atmosphere;	99%
With 2-Picolinic acid; copper(l) iodide In dimethyl sulfoxide at 120℃; for 48h; Inert atmosphere;	55%
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 120℃; for 48h; Inert atmosphere;	55%

2-Bromo-4-picoline (4926-28-7) + 9-phenanthrenylboronic acid (68572-87-2) → 4-methyl-2-(phenanthren-9-yl)pyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 24h; Suzuki Coupling; Inert atmosphere;	98.9%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 80℃; for 24h; Inert atmosphere;	98.9%

2-Bromo-4-picoline (4926-28-7) + 1-bromo-1-propene (590-14-7) → (E)-4-methyl-2-(prop-1-en-1-yl)pyridine

Conditions	Yield
With potassium fluoride; bis(1,5-cyclooctadiene)nickel (0); N,N-dimethyl acetamide; 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; zinc at 0 - 20℃; for 15h; Schlenk technique; Sealed tube; Inert atmosphere; chemoselective reaction;	98%

2-Bromo-4-picoline (4926-28-7) + 2-methoxy-9H-carbazole (6933-49-9) → 2-methoxy-9-(4-methylpyridin-2-yl)-9H-carbazole

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 125℃; for 18h; Inert atmosphere;	98%

2-Bromo-4-picoline (4926-28-7) + 1-bromo-1-propene (590-14-7) → 2-propenyl-4-methylpyridine

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; zinc In N,N-dimethyl acetamide at 20℃; Schlenk technique; Cooling with ice;	98%

2-Bromo-4-picoline (4926-28-7) → 2-iodo-4-methylpyridine (22282-60-6)

Conditions	Yield
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 18h; Finkelstein Reaction; Inert atmosphere; Schlenk technique;	97%
Stage #1: 2-Bromo-4-picoline With nBu4ZnLi2*TMEDA In toluene at 20℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; toluene at 20℃; for 1h; Inert atmosphere; chemoselective reaction;	88%

2-Bromo-4-picoline (4926-28-7) + 1-Naphthylboronic acid (13922-41-3) → 4-methyl-2-(naphthalen-1-yl)pyridine (100004-76-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In toluene Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;	97%
With tetrakis(triphenylphosphine) palladium(0); 1-chloroisoquinoline; sodium carbonate In ethanol; water; toluene at 120℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique;

2-Bromo-4-picoline (4926-28-7) + 4-methyl-1-naphthylboronic acid (103986-53-4) → C17H15N

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In toluene Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;	97%

2-Bromo-4-picoline (4926-28-7) + 4-(diphenylamino)phenyl boronic acid (201802-67-7) → N,N-diphenyl-4-(4-methylpyridinyl-2-yl)aniline (1422183-04-7)

Conditions	Yield
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 0.133333h; Suzuki Coupling;	96%
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; Suzuki Coupling;
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 1h; Suzuki Coupling;

2-Bromo-4-picoline (4926-28-7) + 2-methoxyphenylmagnesium bromide (16750-63-3) → 2-(2-methoxyphenyl)-4-methylpyridine (100004-77-1)

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran	96%

2-Bromo-4-picoline (4926-28-7) + methyl 2-[(tert-butoxycarbonyl)amino]acrylate (55477-80-0) → C15H22N2O4

Conditions	Yield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In water; dimethyl sulfoxide at 23℃; for 16h; Irradiation;	96%

2-Bromo-4-picoline (4926-28-7) + C10H11BrClMgNSi*LiCl → 3-bromo-4'-methyl-6-((trimethylsilyl)ethynyl)-2,2'-bipyridine

Conditions	Yield
Stage #1: 2-Bromo-4-picoline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: With magnesium chloride In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #3: C10H11BrClMgNSi*LiCl Further stages;	96%

2-Bromo-4-picoline (4926-28-7) + aniline (62-53-3) → 4-methyl-N-phenyl-2-aminopyridine (19933-06-3)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 100℃; Inert atmosphere;	95%
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 100℃; Inert atmosphere;	90%
With copper at 140 - 150℃; under 40 Torr; Badtemperatur;

2-Bromo-4-picoline (4926-28-7) + phenylmagnesium chloride (100-59-4) → 4-methyl-2-phenylpyridine (3475-21-6)

Conditions	Yield
1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at -25℃; for 18h;	95%

2-Bromo-4-picoline (4926-28-7) + phenylboronic acid (98-80-6) → 4-methyl-2-phenylpyridine (3475-21-6)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran at 60℃; for 12h; Schlenk technique; Inert atmosphere;	95%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol at 100℃; for 15h; Inert atmosphere;	94%
With palladium diacetate; potassium carbonate; triphenylphosphine In methanol; acetonitrile at 65℃; for 24h; Inert atmosphere;	85%

2-Bromo-4-picoline (4926-28-7) + 3,4-ethylenedioxythiophene-2-carboxaldehyde (204905-77-1) → 2-(2-bromopyrid-4-yl)-1-(3,4-ethylenedioxythien-2-yl)ethanol (1281847-13-9)

Conditions	Yield
Stage #1: 2-Bromo-4-picoline With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Stage #2: 3,4-ethylenedioxythiophene-2-carboxaldehyde In tetrahydrofuran at 20℃; for 0.5h; Stage #3: With water In tetrahydrofuran; ethyl acetate	95%
Stage #1: 2-Bromo-4-picoline With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Stage #2: 3,4-ethylenedioxythiophene-2-carboxaldehyde In tetrahydrofuran at 20℃; for 0.5h; Stage #3: With water In tetrahydrofuran; ethyl acetate	95%
Stage #1: 2-Bromo-4-picoline With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Stage #2: 3,4-ethylenedioxythiophene-2-carboxaldehyde In tetrahydrofuran at 20℃; for 0.5h;	94%

2-Bromo-4-picoline (4926-28-7) + 2-bromo-9H-carbazole (3652-90-2) → 2-bromo-9-(4-methylpyridine-2-yl)-9H-carbazole (1404169-08-9)

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 2.5h; Inert atmosphere;	95%
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 2.5h; Ullmann Condensation; chemoselective reaction;	95%
With 1-methyl-1H-imidazole; copper(l) iodide; lithium tert-butoxide In toluene at 20 - 130℃; for 48h; Inert atmosphere;	95%

2-Bromo-4-picoline (4926-28-7) + 1-butyn-4-ol (927-74-2) → 4-(4-methylpyridin-2-yl)but-3-yn-1-ol

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 24h; Sonogashira Cross-Coupling; Inert atmosphere;	95%

2-Bromo-4-picoline (4926-28-7) + C14H13NO → C20H18N2O

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) iodide; lithium tert-butoxide In toluene Inert atmosphere; Heating; Sealed tube;	95%

2-Bromo-4-picoline (4926-28-7) + (4S)-4-isopropyl-1,3-oxazolidin-2-one (17016-83-0) → (S)-4-isopropyl-3-(4-methylpyridin-2-yl)oxazolidin-2-one (737760-93-9)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In toluene at 140℃; for 16h; Inert atmosphere; Schlenk technique;	95%

2-Bromo-4-picoline (4926-28-7) + 4-fluoro-N-methoxy-N-methylbenzamide (116332-54-8) → 2-(2-bromopyridin-4-yl)-1-(4-fluorophenyl)ethan-1-one (158876-70-1)

Conditions	Yield
Stage #1: 2-Bromo-4-picoline With lithium diisopropyl amide In tetrahydrofuran; hexane at -85℃; Stage #2: 4-fluoro-N-methoxy-N-methylbenzamide In tetrahydrofuran; hexane at -85 - 0℃;	94%

2-Bromo-4-picoline (4926-28-7) + 2-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy)-9H-carbazole (1393812-51-5) → 2-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy)-9-(4-methylpyridin-2-yl)-9H-carbazole

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In 1,4-dioxane; toluene at 95 - 105℃; for 48h; Inert atmosphere; Sealed tube;	94%
With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In 1,4-dioxane; toluene at 95 - 105℃; for 48h; Schlenk technique; Inert atmosphere; Sealed tube;	94%

2-Bromo-4-picoline (4926-28-7) + 4-dibenzofurylboronic acid (100124-06-9) → 2-(dibenzo[b,d]furan-4-yl)-4-methylpyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; ethanol; water for 24h; Suzuki-Miyaura Coupling; Reflux; Inert atmosphere;	94%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 2h;	67%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 2h;	67%

2-Bromo-4-picoline (4926-28-7) + 3-(trimethylsilyl)phenylboronic acid (177171-16-3) → 4-methyl-2-(3-trimethylsilylphenyl)pyridine

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 18h; Heating;	93%

2-Bromo-4-picoline (4926-28-7) + 2,4-difluorophenylboronic acid (144025-03-6) → 2-(2',4'-difluorophenyl)-4-methylpyridine (391250-41-2)

Conditions	Yield
Stage #1: 2-Bromo-4-picoline; 2,4-difluorophenylboronic acid With potassium carbonate In 1,2-dimethoxyethane for 0.5h; Stage #2: tetrakis(triphenylphosphine) palladium(0) In water-d2 at 90℃; for 18h; Heating / reflux;	93%
Stage #1: 2-Bromo-4-picoline; 2,4-difluorophenylboronic acid With potassium carbonate In 1,2-dimethoxyethane for 0.5h; Stage #2: tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 90℃; for 18h; Heating / reflux;	93%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; ethanol for 24h; Reflux; Inert atmosphere;	89%

Upstream product

• 4021-08-3 4-methylpicolinic acid 
• 695-34-1 2-Amino-4-methylpyridine 
• 13466-41-6 2-hydroksy-4-methyl-pyridine 
• 75-25-2 Bromoform 
• 108-89-4 picoline 
• 78948-09-1 acetyl hypofluorite 

Downstream Products

• 3475-21-6 4-methyl-2-phenylpyridine 
• 446852-65-9 2-(2-bromopyridin-4-yl)-1-(pyridin-2-yl)ethan-1-one 
• 222551-24-8 2-(4-fluorophenyl)-4-methylpyridine 
• 80635-97-8 2-(4-isopropylphenyl)-4-methylpyridine 
• 23182-19-6 2-(4-chlorophenyl)-4-methylpyridine 
• 452342-99-3 4-methyl-2-[4-(trifluoromethyl)phenyl]pyridine 
• 82226-09-3 (4-methylpyridin-2-yl)-3-phenylmethanol 
• 13959-34-7 4-methyl-2-vinylpyridine 
• 80636-01-7 2-(4-methoxyphenyl)-4-methylpyridine 
• 289469-97-2 4-(4-methylpyridin-2-yl)benzaldehyde 
• 83004-14-2 2-bromo-4-bromomethyl pyridine 
• 88443-57-6 2-bromo-4-dimethylaminomethylpyridine 
• 656257-50-0 2-(4-bromophenyl)-4-methylpyridine 
• 446880-80-4 2-(2-bromopyridin-4-yl)-1-(6-methylpyridin-2-yl)ethan-1-one 

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