3510-66-5

Basic information

• Product Name: 2-Bromo-5-methylpyridine
• Synonyms: 6-BROMO-3-PICOLINE;2-BROMO-5-PICOLINE;2-BROMO-5-METHYLPYRIDINE;2-BROMO-5-METHYLPYRIDINE 98%;2-Bromo5MythylPyridine;2-BROMO-5-METHYLPYRIDINE (2-BROMO-5-PICOLINE);2-Bromo-5-methylpyridine, 98+%;6-Bromo-β-picoline
• CAS NO: 3510-66-5
• Molecular Formula: C₆H₆BrN
• Molecular Weight: 172.02
• EINECS: -0
• Product Categories: compounds of pyridine;blocks;Bromides;Pyridines;Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;Pyridine series;Pyridines derivates;Aromatics Compounds;Bromopyridines;Halopyridines;Aromatics;Heterocycles;Boronic Acid;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocycle-Pyridine series;alkyl bromide
• Mol File: 3510-66-5.mol
• Article Data: 30

Chemical Properties

• Melting Point: 41-43 °C(lit.)
• Boiling Point: 95-96 °C12.5 mm Hg(lit.)
• Flash Point: 218 °F
• Appearance: White to light yellow or pale brown/Low Melting Crystalline Solid or Crystals
• Density: 1.4964 (rough estimate)
• Vapor Pressure: 0.183mmHg at 25°C
• Refractive Index: 1.5680 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Dimethyl Sulfoxide, Methanol,
• PKA: 1.08±0.10(Predicted)
• BRN: 107323
• CAS DataBase Reference: 2-Bromo-5-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-5-methylpyridine(3510-66-5)
• EPA Substance Registry System: 2-Bromo-5-methylpyridine(3510-66-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36/37/39-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3510-66-5(Hazardous Substances Data)

Usage

Chemical Properties

2-Bromo-5-methylpyridine is Light Brown Solid

Uses

Different sources of media describe the Uses of 3510-66-5 differently. You can refer to the following data:
1. 2-Bromo-5-methylpyridine is used for preparation of [[(triazolylmethyl)pyridyl]phenyl]tetrazoles and related compounds as cardiovascular agents.
2. 2-Bromo-5-methylpyridine has been used as starting reagent for the synthesis of:5,5′-dimethyl-2,2′-bipyridine5-methyl-2,2′:6′,2″-terpyridine5-bromo-5″-methyl-2,2′:6′,2″-terpyridine

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

Synthetic route

(5-methyl-pyridin-2-yl)amine (1603-41-4) → 2-Bromo-5-methylpyridine (3510-66-5)

Conditions	Yield
With hydrogen bromide; bromine; sodium nitrite 1.) -20 deg C, 90 min; 2.) 15 deg C, 1 h 45 min;	93%
With hydrogen bromide; bromine; sodium nitrite at 0℃;	91%
Stage #1: (5-methyl-pyridin-2-yl)amine With hydrogen bromide; bromine In water at -20℃; for 3h; Stage #2: With sodium nitrite at -20℃; for 1h;	90%

(5-methyl-pyridin-2-yl)amine (1603-41-4) → 2-Bromo-5-methylpyridine (3510-66-5) + 3-[4-(5-methylpyrid-2-yl)piperazin-1-yl]methyl-1H-pyrrolo[2,3-b]pyridine

Conditions	Yield
With sodium hydroxide; bromine; sodium nitrite In water; hydrogen bromide	A n/a B 75%

3-Methylpyridine (108-99-6) → 2-Bromo-5-methylpyridine (3510-66-5)

Conditions	Yield
Stage #1: 3-Methylpyridine With n-butyllithium; lithium 2-(dimethylamino)ethanolate In hexane at 0℃; for 1h; Metallation; Stage #2: With carbon tetrabromide In tetrahydrofuran; hexane at -78℃; for 1h; Substitution; Further stages.;	65%
Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / diethyl ether / 0.17 h / 0 °C / Inert atmosphere 2.1: n-butyllithium; diisopropylamine / diethyl ether / 0.42 h / -78 °C 2.2: -78 - 20 °C View Scheme

5-methyl-pyridin-2-ol (1003-68-5) → 2-Bromo-5-methylpyridine (3510-66-5)

Conditions	Yield
With phosphorus tribromide at 190℃;

6-hydroxy-3-methylpicolinic acid (115185-81-4) → 2-Bromo-5-methylpyridine (3510-66-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper-powder / 300 °C 2: phosphorus (III)-bromide / 190 °C View Scheme

5-methyl-6-carboxy-2-pyrone (3060-42-2) → 2-Bromo-5-methylpyridine (3510-66-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: aqueous NH3 / 120 - 140 °C 2: copper-powder / 300 °C 3: phosphorus (III)-bromide / 190 °C View Scheme

(5-methyl-pyridin-2-yl)amine (1603-41-4) + ice-ethanol → 2-Bromo-5-methylpyridine (3510-66-5)

Conditions	Yield
With sodium hydroxide; bromine; sodium hydrogensulfite; sodium nitrite In hexane; water

2,5-dibromopyridine (624-28-2) + methyl iodide (74-88-4) → 2-Bromo-5-methylpyridine (3510-66-5)

Conditions	Yield
Stage #1: 2,5-dibromopyridine With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1.52778E-05h; Stage #2: methyl iodide In tetrahydrofuran; hexane at 0℃; for 0.0025h;	84 %Chromat.
Stage #1: 2,5-dibromopyridine With n-butyllithium In hexane at 0℃; for 1.52778E-05h; Stage #2: methyl iodide In tetrahydrofuran; hexane at 0℃; for 0.0025h;	84 %Chromat.

(3-methylpyridine)BF3 (6457-37-0) → 2-Bromo-5-methylpyridine (3510-66-5)

Conditions	Yield
Stage #1: (3-methylpyridine)BF3 With n-butyllithium; diisopropylamine In diethyl ether at -78℃; for 0.416667h; Stage #2: With bromine In diethyl ether at -78 - 20℃; Stage #3: With water In diethyl ether regioselective reaction;	1.05 g

2-chloro-5-methylpyridine (18368-64-4) → 2-Bromo-5-methylpyridine (3510-66-5)

Conditions	Yield
With hydrogen bromide; lithium bromide Reflux;

2-carboxy-5-methylpyridine (4434-13-3) → 2-Bromo-5-methylpyridine (3510-66-5)

Conditions	Yield
With tert-butylhypochlorite; dichloromethane; oxygen; sodium hydrogencarbonate at 70℃; for 30h; Green chemistry;	40 %Spectr.

2-bromo-pyridine (109-04-6) + 2-Bromo-5-methylpyridine (3510-66-5) → 5-methyl-2,2'-bipyridine (56100-20-0)

Conditions	Yield
Stage #1: 2-bromo-pyridine With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h; Stage #2: With zinc(II) chloride In tetrahydrofuran; pentane at 20℃; for 2.5h; Stage #3: 2-Bromo-5-methylpyridine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; pentane at 20℃; for 18h; Negishi cross-coupling reaction; Further stages.;	100%
Stage #1: 2-bromo-pyridine With tert.-butyl lithium In tetrahydrofuran at -78℃; Stage #2: With zinc(II) chloride In tetrahydrofuran at -78 - 20℃; Stage #3: 2-Bromo-5-methylpyridine With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃;	73%

2-Bromo-5-methylpyridine (3510-66-5) + phenylboronic acid (98-80-6) → 5-methyl-2-phenylpyridine (27012-22-2)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux;	100%
With potassium phosphate tribasic heptahydrate; palladium diacetate In ethylene glycol at 80℃; for 0.583333h; Suzuki coupling;	99%
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 0.333333h; Suzuki Coupling;	96%

2-Bromo-5-methylpyridine (3510-66-5) → (5-methyl-pyridin-2-yl)amine (1603-41-4)

Conditions	Yield
With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 120℃; for 16h; Sealed tube;	100%
With ammonium hydroxide; potassium phosphate; 1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-1-one; copper(I) bromide In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; Sealed tube;	85%

4-(carbazol-9-yl)phenylboronic acid (419536-33-7) + 2-Bromo-5-methylpyridine (3510-66-5) → 9-(4-(5-methylpyridin-2-yl)phenyl)-9H-carbazole (1380225-65-9)

Conditions	Yield
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 0.333333h; Suzuki Coupling;	99%
With palladium diacetate; potassium carbonate In ethanol; water at 80℃;

2-Bromo-5-methylpyridine (3510-66-5) + (5-(tert-butyl)-2-methoxyphenyl)boronic acid (128733-85-7) → 2-(5-(tert-butyl)-2-methoxyphenyl)-5-methylpyridine (1609654-41-2)

Conditions	Yield
Stage #1: 2-Bromo-5-methylpyridine; (5-(tert-butyl)-2-methoxyphenyl)boronic acid With potassium carbonate In 1,2-dimethoxyethane; water for 0.333333h; Suzuki Coupling; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 80℃; for 22h; Suzuki Coupling; Inert atmosphere; Sealed tube;	99%

2-Bromo-5-methylpyridine (3510-66-5) + 2-methoxyphenylmagnesium bromide (16750-63-3) → 2-(2-methoxyphenyl)-5-methyl-pyridine (884494-43-3)

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran	99%

2-Bromo-5-methylpyridine (3510-66-5) + 1-tert-Butyl 4-methyl piperidine-1,4-dicarboxylate (124443-68-1) → 1-tert-butyl 4-methyl 4-(5-methylpyridin-2-yl)piperidine-1,4-dicarboxylate

Conditions	Yield
With lithium hexamethyldisilazane; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In toluene at 23℃; for 12h;	95%

2-Bromo-5-methylpyridine (3510-66-5) + 4-methoxyphenylboronic acid (5720-07-0) → 2-(4-methoxylphenyl)-5-methylpyridine (25363-55-7)

Conditions	Yield
With [Pd(Cl)κ2-S,N-C6H4CS=N-(4-Py)(PPh3)]; potassium carbonate In toluene at 80℃; for 5h; Suzuki coupling;	95%
With C28H23ClN3PPdS2; potassium carbonate In water; isopropyl alcohol at 80℃; for 5h; Suzuki-Miyaura Coupling;	89%
With potassium phosphate tribasic heptahydrate; palladium diacetate In isopropyl alcohol at 80℃; for 1h; Suzuki coupling;	85%

1H-imidazole (288-32-4) + 2-Bromo-5-methylpyridine (3510-66-5) → 2-(imidazol-1-yl)-5-methylpyridine (1343101-24-5)

Conditions	Yield
With potassium carbonate In neat (no solvent) at 190℃; for 18h; Schlenk technique; Inert atmosphere;	95%
With copper(l) iodide; potassium carbonate; L-proline In dimethyl sulfoxide at 100℃; for 24h; Ullmann Condensation;

2-Bromo-5-methylpyridine (3510-66-5) + 9H-carbazole (86-74-8) → 9-(4-methylpyridin-2-yl)-9H-carbazole (1570075-58-9)

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 11h; Ullmann Condensation;	95%

2-Bromo-5-methylpyridine (3510-66-5) + 3-phenyl-2H-thiete 1,1-dioxide (25903-17-7) → 4-(5-Methylpyridin-2-yl)-3-phenyl-2H-thiete 1,1-dioxide

Conditions	Yield
With palladium diacetate; potassium carbonate; tricyclohexylphosphine; Trimethylacetic acid In toluene at 120℃; for 16h; Inert atmosphere; Sealed tube;	95%

2-Bromo-5-methylpyridine (3510-66-5) + copper(II) bromide dihydrate → [Cu(2-bromo-5-methylpyridine)2Br2]

Conditions	Yield
In ethanol	95%

2-Bromo-5-methylpyridine (3510-66-5) + sodium methylate (124-41-4) → 2-methoxy-5-methylpyridine (13472-56-5)

Conditions	Yield
In methanol at 20 - 80℃; for 12h; Cooling with ice;	94.3%
polyethylene glycol dimethyl ether; copper(I) bromide In methanol at 90℃; for 17h;	91%

2-Bromo-5-methylpyridine (3510-66-5) + hex-1-yne (693-02-7) → 2-hex-1-ynyl-5-methyl-pyridine

Conditions	Yield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride at 60℃; for 1.5h;	94%

2-Bromo-5-methylpyridine (3510-66-5) + 4-(diphenylamino)phenyl boronic acid (201802-67-7) → N,N-diphenyl-4-(5-methylpyridinyl-2-yl)aniline (1263145-40-9)

Conditions	Yield
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 0.333333h; Suzuki Coupling;	94%
With potassium phosphate tribasic heptahydrate; palladium diacetate In water; isopropyl alcohol at 80℃; for 0.666667h; Suzuki reaction;	93%
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; Suzuki Coupling;
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-5-methylpyridine (3510-66-5) + 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-(5-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; Schlenk technique; Inert atmosphere; Sealed tube;	94%

2-Bromo-5-methylpyridine (3510-66-5) + 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;	93%

2-Bromo-5-methylpyridine (3510-66-5) + 1,4-di(pyrimidin-2-yl)benzene (174303-49-2) → 2,2'-(2,3,5,6-tetrakis(5-methylpyridin-2-yl)-1,4-phenylene)dipyrimidine

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium pivalate; sodium carbonate; triphenylphosphine In water at 200℃; for 4h; Inert atmosphere; Microwave irradiation;	93%

2-Bromo-5-methylpyridine (3510-66-5) + 6-amino-1H-indazole-7-carboxylic acid methyl ester (73907-98-9) → 9-methylpyrazolo[3,4-f]pyrido[2,1-b]quinazolin-12(1H)-one

Conditions	Yield
With 1,8-Cineole; palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 120℃; Buchwald-Hartwig Coupling;	93%

2-Bromo-5-methylpyridine (3510-66-5) + 4-formylphenylboronic acid, (87199-17-5) → 2-(4-formylphenyl)-5-methylpyridine (1008744-15-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 90℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	92%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 110℃; for 6h;

Upstream product

• 1003-68-5 5-methyl-pyridin-2-ol 
• 108-99-6 3-Methylpyridine 
• 624-28-2 2,5-dibromopyridine 
• 74-88-4 methyl iodide 
• 18368-64-4 2-chloro-5-methylpyridine 
• 4434-13-3 2-carboxy-5-methylpyridine 
• 6457-37-0 (3-methylpyridine)BF₃ 
• 1603-41-4 (5-methyl-pyridin-2-yl)amine 
• 3060-42-2 5-methyl-6-carboxy-2-pyrone 
• 115185-81-4 6-hydroxy-3-methylpicolinic acid 

Downstream Products

• 6311-35-9 6-bromonicotinic acid 
• 1762-34-1 5,5'-dimethyl-2,2'-bipyridine 
• 5825-11-6 (Z)-2-styryl-5-methylpyridine 
• 7370-20-9 (E)-2-styryl-5-methylpyridine 
• 201403-32-9 2-(p-methoxyphenyl)-9-(5'-methylpyridin-2'-yl)-1,10-phenanthroline 
• 1620-77-5 5-methylpicolinonitrile 
• 56100-20-0 5-methyl-2,2'-bipyridine 
• 371784-97-3 5-methyl-2-(prop-1-yn-1-yl)pyridine 
• 34123-86-9 5-methyl-2-(4-chlorophenyl)pyridine 
• 503627-67-6 2,2-difluoro-2-(5-methylpyridine-2-yl)acetic acid ethyl ester 
• 108-99-6 3-Methylpyridine 
• 51933-81-4 5-methyl-2-phenoxypyridine 
• 851775-42-3 2-(3-methylphenyl)-5-methylpyridine 
• 85237-71-4 2-(4-methylphenyl)-5-methylpyridine 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF ABAMETAPIR AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

The present invention relates to process for the preparation of Abametapir. The present 5 invention further relates to Abametapir salts and their preparation thereof.

Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide

A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.

2,6-DIOXO,-2,3-DIHYDRO-1H-PURINE COMPOUNDS USEFUL FOR TREATING DISORDERS RELATED TO THE ACTIVITY OF THE TRPA1 CHANNEL

Compounds of formula (VIII) and compositions for treating disorders related to TRPA1 are described herein.