3430-17-9

Basic information

• Product Name: 2-Bromo-3-methylpyridine
• Synonyms: 2-BROMO-3-METHYLPYRIDINE;2-BROMO-3-PICOLINE;2-BROMO-3-METHYLPYRIDINE 98%;2-BROMO-3-METHYLPYRIDINE (2-BROMO-3-PICOLINE);2-Bromo-3-methylpyridine, 98+%;2-bormo-3-methylpyridine;2-Bromo-3-methylpyridine,95%;2-BroMo-3-Methylpyridine, 95% 25ML
• CAS NO: 3430-17-9
• Molecular Formula: C₆H₆BrN
• Molecular Weight: 172.02
• EINECS: -0
• Product Categories: blocks;Bromides;Pyridines;Pyridine;Pyridine Series;Indoles and derivatives;Halides;Pyridines derivates;Bromopyridines;Halopyridines;Boronic Acid;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Brominated heterocyclic series;OLED materials,pharm chemical,electronic;alkyl bromide
• Mol File: 3430-17-9.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 218-219 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear slightly yellow to light brown/Liquid
• Density: 1.544 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.218mmHg at 25°C
• Refractive Index: n20/D 1.568(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 1.08±0.10(Predicted)
• BRN: 107896
• CAS DataBase Reference: 2-Bromo-3-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-3-methylpyridine(3430-17-9)
• EPA Substance Registry System: 2-Bromo-3-methylpyridine(3430-17-9)

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
• PackingGroup: III
• Hazardous Substances Data: 3430-17-9(Hazardous Substances Data)

Usage

Chemical Properties

clear slightly yellow to light brown liquid

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

Synthetic route

3-methylpyridin-2-ylamine (1603-40-3) → 2-bromo-3-picoline (3430-17-9)

Conditions	Yield
With hydrogen bromide; bromine; sodium nitrite at 5℃;	88%
With hydrogen bromide; bromine; sodium nitrite In water; triethylamine at -20℃;	88%
With hydrogen bromide; bromine; sodium nitrite at 0℃;	80%

3-methylpyridin-2-ol (1003-56-1, 91914-04-4) → 2-bromo-3-picoline (3430-17-9)

Conditions	Yield
With phosphorus tribromide at 190℃;

2,6-Dibromopyridine (626-05-1) + methyl iodide (74-88-4) → 2-bromo-3-picoline (3430-17-9)

Conditions	Yield
Yield given. Multistep reaction;

2-bromo-pyridine (109-04-6) + methyl iodide (74-88-4) → 2-bromo-3-picoline (3430-17-9)

Conditions	Yield
With lithium diisopropyl amide 1.) THF, -70 deg C, 4 h, 2.) THF; Yield given. Multistep reaction;

2,3-dibromopyridine (13534-89-9) + methyl iodide (74-88-4) → 2-bromo-pyridine (109-04-6) + 2-bromo-3-picoline (3430-17-9)

Conditions	Yield
Stage #1: 2,3-dibromopyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.183333h; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; for 0.183333h;	A 24 %Chromat. B 48 %Chromat.
Stage #1: 2,3-dibromopyridine With n-butyllithium In tetrahydrofuran; hexane at -48℃; for 0.183333h; Stage #2: methyl iodide In tetrahydrofuran; hexane at -48℃; for 0.183333h;	A 26 %Chromat. B 19 %Chromat.

2-bromo-3-picoline (3430-17-9) + 8-methoxy-naphthalen-1-ylboronic acid → 8'-methoxy-1'-(3-methylpyridin-2-yl)naphthalene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water at 100℃; for 3.5h; Suzuki-Miyaura coupling reaction;	100%

2-bromo-3-picoline (3430-17-9) + 5-methoxy-2-(N,N-diethylcarboxamido)phenylboronic acid (185033-59-4) → N,N-diethyl-4-methoxy-2-(3-methylpyridin-2-yl)benzamide (958219-58-4)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water for 5h; Heating / reflux;	100%

2-bromo-3-picoline (3430-17-9) + acetonitrile (75-05-8) → (3-methyl-pyridin-2-yl)-acetonitrile (38203-11-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 2.08333h;	100%
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 4h;	91%

2-bromo-3-picoline (3430-17-9) + N-Boc-indole-2-boronic acid (213318-44-6) → tert-Butyl 2-(3-methyl-2-pyridyl)-1H-indole-1-carboxylate (290331-74-7)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane for 18h; Arylation; Suzuki reaction; Heating;	99%

2-bromo-3-picoline (3430-17-9) + [(1,10-phenanthroline)2Cu][OCH2CF3] → 3-methyl-2-(2,2,2-trifluoroethoxy)pyridine

Conditions	Yield
With sodium t-butanolate In N,N-dimethyl-formamide at 80℃; for 12h; Sealed tube;	99%
With sodium t-butanolate In N,N-dimethyl-formamide at 80℃;	96%
With sodium t-butanolate In N,N-dimethyl-formamide at 80℃; for 12h; Sealed tube; Inert atmosphere;	99 %Spectr.

2-bromo-3-picoline (3430-17-9) + 1-Naphthylboronic acid (13922-41-3) → 3-methyl-2-(naphthalen-1-yl)pyridine

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 1-(7-benzofuranyl)-2-di(3,5-di-tert-butyl-4-methoxyphenyl)phosphinenaphthalene In toluene at 80℃; for 3h; Reagent/catalyst; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere;	99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water for 24h; Inert atmosphere; Schlenk technique; Reflux;	95%
With 2C32H41O4P*Pd(2+)*2Cl(1-); water In tetrahydrofuran at 60℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere;	92%
With tetrakis(triphenylphosphine) palladium(0); 1-chloroisoquinoline; sodium carbonate In ethanol; water; toluene at 120℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique;

2-bromo-3-picoline (3430-17-9) + 1,3,5-tri(pyridin-2-yl)benzene (124960-21-0) → 2,2',2''-(2,4,6-tri(pyridin-2-yl)benzene-1,3,5-triyl)tris(3-methylpyridine)

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;	96%

2-bromo-3-picoline (3430-17-9) + 1,4-Phenyldiboronic acid (4612-26-4) → 1,4-bis(3-methylpyridin-2-yl)benzene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere;	96%

2-bromo-3-picoline (3430-17-9) + 2-methyl-4-(pyrid-2-yl)but-3-yn-2-ol (29767-97-3) → 3-methyl-2-(pyridin-2'-ylethynyl)pyridine (1137275-98-9)

Conditions	Yield
With copper(l) iodide; palladium 10% on activated carbon; triethylamine; triphenylphosphine; sodium hydroxide In acetonitrile at 76℃; for 23h; Sonogashira coupling; Inert atmosphere;	95%

2-bromo-3-picoline (3430-17-9) + trimethylsilylacetylene (1066-54-2) → C11H15NSi

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 12h;	95%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Inert atmosphere;	65.8%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20 - 70℃; for 6h;

2-bromo-3-picoline (3430-17-9) + bis[4-(dimethylamino)phenyl]zinc → 2-(4-(N,N-dimethylamino)phenyl)-3-methylpyridine (31640-78-5)

Conditions	Yield
With dichloro{bis[1-(dicyclohexylphosphanyl)piperidine]}palladium(II) In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 100℃; for 15h; Negishi cross-coupling reaction; In air;	94%

2-bromo-3-picoline (3430-17-9) + [3-(ethoxycarbonyl)phenyl]boronic acid (4334-87-6) → ethyl 3-(3-methylpyridin-2-yl)benzoate

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; toluene at 80℃; for 2h; Inert atmosphere;	94%

2-bromo-3-picoline (3430-17-9) + 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;	94%

2-bromo-3-picoline (3430-17-9) + pyrrole (109-97-7) → 3-methyl-2-(1H-pyrrol-1-yl)pyridine

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 120℃; for 18h;	94%

2-bromo-3-picoline (3430-17-9) + methanol (67-56-1) + carbon monoxide (201230-82-2) → 3-methyl-pyridine-2-carboxylic acid methyl ester (59718-84-2)

Conditions	Yield
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine at 80℃; under 2585.81 Torr; for 16h;	93.6%

2-bromo-3-picoline (3430-17-9) + 4-Phenyl-1-butyne (16520-62-0) → 3-methyl-2-(4-phenylbut-1-yn-1-yl)pyridine (1428857-27-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 60℃; for 1h; Sonogashira Cross-Coupling;	93%

2-bromo-3-picoline (3430-17-9) + 3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) → tert-butyl 3-(3-methylpyridin-2-yl)benzoate (1083057-12-8)

Conditions	Yield
Stage #1: 2-bromo-3-picoline With potassium carbonate In water; toluene at 65℃; Inert atmosphere; Stage #2: 3-(tert-butoxycarbonyl)phenylboronic acid With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; toluene for 18h; Inert atmosphere; Reflux;	92%
Stage #1: 2-bromo-3-picoline With potassium carbonate In water; toluene at 65℃; for 1h; Stage #2: 3-(tert-butoxycarbonyl)phenylboronic acid; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; toluene at 80℃; for 2h;	82%
Stage #1: 2-bromo-3-picoline With potassium carbonate In toluene at 65℃; for 1h; Inert atmosphere; Stage #2: 3-(tert-butoxycarbonyl)phenylboronic acid With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In toluene at 80℃; for 2h; Inert atmosphere;	82%

2-bromo-3-picoline (3430-17-9) + Triisopropyl borate (5419-55-6) → (3-methylpyridin-2-yl)boronic acid

Conditions	Yield
Stage #1: 2-bromo-3-picoline With isopropylmagnesium chloride In tetrahydrofuran; diethyl ether at 0℃; for 3h; Stage #2: Triisopropyl borate In tetrahydrofuran; Dimethyl ether at 20℃; for 1h;	92%

2-bromo-3-picoline (3430-17-9) + C15H21ClMgN2*LiCl → 6-(3-methylpyridin-2-yl)-1-octyl-1H-pyrrolo[2,3-b]pyridine

Conditions	Yield
Stage #1: 2-bromo-3-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: C15H21ClMgN2*LiCl Further stages;	92%

2-bromo-3-picoline (3430-17-9) + (3-methylpyridin-2-yl)(phenyl)(p-tolyl)sulfonium trifluoromethanesulfonate → 3,3'-dimethyl-2,2'-bipyridine (1762-32-9)

Conditions	Yield
Stage #1: 2-bromo-3-picoline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.533333h; Sealed tube; Inert atmosphere; Stage #2: (3-methylpyridin-2-yl)(phenyl)(p-tolyl)sulfonium trifluoromethanesulfonate In tetrahydrofuran; hexane at -78℃; for 2h; Sealed tube; Inert atmosphere;	92%

2-bromo-3-picoline (3430-17-9) + di(1-adamantyl) ketone (38256-01-8) → [2-(3-methylpyridyl)]di(1-adamantyl)methanol

Conditions	Yield
Stage #1: 2-bromo-3-picoline With n-butyllithium In diethyl ether; pentane at -75℃; for 0.5h; Metallation; Stage #2: di(1-adamantyl) ketone In diethyl ether; pentane at -75 - 0℃; for 2h; Substitution;	91%

Upstream product

• 109-04-6 2-bromo-pyridine 
• 74-88-4 methyl iodide 
• 4021-07-2 3-methyl-pyridine-2-carboxylic acid 
• 13534-89-9 2,3-dibromopyridine 
• 626-05-1 2,6-Dibromopyridine 
• 1003-56-1 3-methylpyridin-2-ol 
• 1603-40-3 3-methylpyridin-2-ylamine 

Downstream Products

• 63065-79-2 (3-methyl-pyridin-2-yl)-phenyl-acetonitrile 
• 35905-85-2 2-bromonicotinic acid 
• 1762-32-9 3,3'-dimethyl-2,2'-bipyridine 
• 175602-48-9 2-(2,4-Di-tert-butyl-6-methoxy-phenyl)-3-methyl-pyridine 
• 68039-43-0 1,3-di-tert-butyl-5-methoxybenzene 
• 210752-31-1 2-(1-phenylethyl-amino)-3-methylpyridine 
• 252358-83-1 2,2',2''-(1,3,5-benzenetriyl)tris[3-methylpyridine] 
• 290331-74-7 tert-Butyl 2-(3-methyl-2-pyridyl)-1H-indole-1-carboxylate 
• 10273-90-2 2-phenyl-3-methylpyridine 
• 503627-61-0 difluoro-(3-methyl-pyridin-2-yl)-acetic acid ethyl ester 
• 19230-57-0 2-bromo-3-methylpyridine 1-oxide 
• 497854-89-4 (4-fluorophenyl)(3-methylpyridin-2-yl)acetonitrile 
• 64291-96-9 3-methyl-2-(4-methylphenyl)pyridine 
• 879005-44-4 2-(2,6-dimethoxyphenyl)-3-methylpyridine 

Relevant articles and documents

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Preparation and characterization of methyl substituted 2,2′-dipyridyl diselenides and -ditellurides: X-ray structure of 6,6′-dimethyl-2,2′-dipyridyl diselenide

A convenient method for the preparation of various methyl substituted 2,2′-dipyridyl diselenides and -ditellurides by the aerial oxidation of lithium 2-pyridylselenolate/tellurolate, prepared from the lithium-halogen exchange between n-butyllithium and 2-bromo methyl substituted pyridines is reported. All the compounds prepared are new and have been characterized by elemental analysis, IR, 1H, 13C, 11Se NMR, and mass spectral studies. Crystal structure of 6,6′-dimethyl-2,2′-dipyridyl diselenide has been determined.

Photophysical behavior of a novel 4-aza-indole derivative in different solvents: reverse solvatochromism

The photophysical properties of a new 4-aza-indole derivative [ethyl 1-((2-(2-ethoxy-2-oxoethyl)pyridin-3-yl)carbamoyl)-2-hydroxy-1H-pyrrolo-[3,2-b]pyridine-3-carboxylate, 12] were determined in different solvents. Compound 12 exhibited an absorbance peak at 340–360?nm with high fluorescence intensity in the wavelength range from 405 to 417?nm in all solvents except N,N-dimethylformamide (DMF). Compound 12 exhibited reverse solvatochromism behavior depending on the solvent polarity. Furthermore, compound 12 showed very high quantum yield in all solvents independent of their polarity. The results suggest that this novel dye could be used for many applications, e.g., as a labeling agent and in bio- or analytical sensors and/or optoelectronic devices.

NEW COMPOUND

PROBLEM TO BE SOLVED: To provide a new compound that does not have structural similarity to ceramide and has excellent CERT inhibitory activity. SOLUTION: The present invention provides a new compound of structural formula (I). A bond group -X- is cis-cyclopropyl-, R1, R2, R3, R4, and R5 independently represent a hydrogen atom, a halogen atom, a linear or branched C1-C8 alkyl group that may have a halogen atom, or OR6. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2020,JPOandINPIT