2-Bromo-4-methylpyridine supplier

Name
2-Bromo-4-methylpyridine
EINECS -0
CAS No. 4926-28-7
Article Data29
CAS DataBase
Density 1.494 g/cm³
Solubility
Melting Point 218 - 228oC
Formula C₆H₆BrN
Boiling Point 219.8 °C at 760 mmHg
Molecular Weight 172.024
Flash Point 86.7 °C
Transport Information
Appearance Colorless to orange oily liquid
Safety 26-36-36/37/39
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xi, Xn
Synonyms 4-Picoline,2-bromo- (6CI,7CI,8CI);2-Bromo-4-picoline;4-Methyl-2-bromopyridine;
PSA 12.89000
LogP 2.15250

Synthetic route

: 695-34-1
2-Amino-4-methylpyridine

: 4926-28-7
2-Bromo-4-picoline

Conditions

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%

: 108-89-4
picoline

: 4926-28-7
2-Bromo-4-picoline

Conditions

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%

: 108-89-4
picoline

: 78948-09-1
acetyl hypofluorite

A: 4926-28-7
2-Bromo-4-picoline

B: 108168-80-5
4-methylpyridin-2-yl acetate

Conditions

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

...Expand

: 13466-41-6
2-hydroksy-4-methyl-pyridine

ethyl acetate-water: ethyl acetate-water

: 75-25-2
Bromoform

: 4926-28-7
2-Bromo-4-picoline

Conditions

Conditions	Yield
With phosphorus tribromide In water

...Expand

: 695-34-1
2-Amino-4-methylpyridine

A: 4926-28-7
2-Bromo-4-picoline

B: 83004-14-2
2-bromo-4-bromomethyl pyridine

: 4021-08-3
4-methylpicolinic acid

: 4926-28-7
2-Bromo-4-picoline

Conditions

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

: 4926-28-7
2-Bromo-4-picoline

: 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

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%

: 4926-28-7
2-Bromo-4-picoline

: 100-39-0
benzyl bromide

: 5191-54-8
2-benzyl-4-methyl pyridine

Conditions

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

: 4926-28-7
2-Bromo-4-picoline

: 2-(3-(quinolin-2-yl)phenoxy)-9H-carbazole

: 9-(4-methylpyridin-2-yl)-2-(3-(quinolin-2-yl)phenoxy)-9H-carbazole

Conditions

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

: 4926-28-7
2-Bromo-4-picoline

: 3017-69-4
2-methyl-1-propenylbromide

: 4-methyl-2-(2-methylprop-1-en-1-yl)pyridine

Conditions

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%

: 4926-28-7
2-Bromo-4-picoline

: 591-20-8
3-Bromophenol

: 2-(3-bromophenoxy)-4-methylpyridine

Conditions

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%

: 4926-28-7
2-Bromo-4-picoline

: 68572-87-2
9-phenanthrenylboronic acid

: 4-methyl-2-(phenanthren-9-yl)pyridine

Conditions

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%

: 4926-28-7
2-Bromo-4-picoline

: 590-14-7
1-bromo-1-propene

: (E)-4-methyl-2-(prop-1-en-1-yl)pyridine

Conditions

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%

: 4926-28-7
2-Bromo-4-picoline

: 6933-49-9
2-methoxy-9H-carbazole

: 2-methoxy-9-(4-methylpyridin-2-yl)-9H-carbazole

Conditions

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%

: 4926-28-7
2-Bromo-4-picoline

: 590-14-7
1-bromo-1-propene

: 2-propenyl-4-methylpyridine

Conditions

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%

: 4926-28-7
2-Bromo-4-picoline

: 22282-60-6
2-iodo-4-methylpyridine

Conditions

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%

: 4926-28-7
2-Bromo-4-picoline

: 13922-41-3
1-Naphthylboronic acid

: 100004-76-0
4-methyl-2-(naphthalen-1-yl)pyridine

Conditions

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;

: 4926-28-7
2-Bromo-4-picoline

: 103986-53-4
4-methyl-1-naphthylboronic acid

: C17H15N

Conditions

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

: 4926-28-7
2-Bromo-4-picoline

: 201802-67-7
4-(diphenylamino)phenyl boronic acid

: 1422183-04-7
N,N-diphenyl-4-(4-methylpyridinyl-2-yl)aniline

Conditions

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;

: 4926-28-7
2-Bromo-4-picoline

: 16750-63-3
2-methoxyphenylmagnesium bromide

: 100004-77-1
2-(2-methoxyphenyl)-4-methylpyridine

Conditions

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

: 4926-28-7
2-Bromo-4-picoline

: 55477-80-0
methyl 2-[(tert-butoxycarbonyl)amino]acrylate

: C15H22N2O4

Conditions

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%

: 4926-28-7
2-Bromo-4-picoline

: C10H11BrClMgNSi*LiCl

: 3-bromo-4'-methyl-6-((trimethylsilyl)ethynyl)-2,2'-bipyridine

Conditions

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%

: 4926-28-7
2-Bromo-4-picoline

: 62-53-3
aniline

: 19933-06-3
4-methyl-N-phenyl-2-aminopyridine

Conditions

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;

: 4926-28-7
2-Bromo-4-picoline

: 100-59-4
phenylmagnesium chloride

: 3475-21-6
4-methyl-2-phenylpyridine

Conditions

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

: 4926-28-7
2-Bromo-4-picoline

: 98-80-6
phenylboronic acid

: 3475-21-6
4-methyl-2-phenylpyridine

Conditions

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%

: 4926-28-7
2-Bromo-4-picoline

: 204905-77-1
3,4-ethylenedioxythiophene-2-carboxaldehyde

: 1281847-13-9
2-(2-bromopyrid-4-yl)-1-(3,4-ethylenedioxythien-2-yl)ethanol

Conditions

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%

: 4926-28-7
2-Bromo-4-picoline

: 3652-90-2
2-bromo-9H-carbazole

: 1404169-08-9
2-bromo-9-(4-methylpyridine-2-yl)-9H-carbazole

Conditions

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%

: 4926-28-7
2-Bromo-4-picoline

: 927-74-2
1-butyn-4-ol

: 4-(4-methylpyridin-2-yl)but-3-yn-1-ol

Conditions

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

: 4926-28-7
2-Bromo-4-picoline

: C14H13NO

: C20H18N2O

Conditions

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

: 4926-28-7
2-Bromo-4-picoline

: 17016-83-0
(4S)-4-isopropyl-1,3-oxazolidin-2-one

: 737760-93-9
(S)-4-isopropyl-3-(4-methylpyridin-2-yl)oxazolidin-2-one

Conditions

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

: 4926-28-7
2-Bromo-4-picoline

: 116332-54-8
4-fluoro-N-methoxy-N-methylbenzamide

: 158876-70-1
2-(2-bromopyridin-4-yl)-1-(4-fluorophenyl)ethan-1-one

Conditions

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%

: 4926-28-7
2-Bromo-4-picoline

: 1393812-51-5
2-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy)-9H-carbazole

: 2-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy)-9-(4-methylpyridin-2-yl)-9H-carbazole

Conditions

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%

: 4926-28-7
2-Bromo-4-picoline

: 100124-06-9
4-dibenzofurylboronic acid

: 2-(dibenzo[b,d]furan-4-yl)-4-methylpyridine

Conditions

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%

: 4926-28-7
2-Bromo-4-picoline

: 177171-16-3
3-(trimethylsilyl)phenylboronic acid

: 4-methyl-2-(3-trimethylsilylphenyl)pyridine

Conditions

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

: 4926-28-7
2-Bromo-4-picoline

: 144025-03-6
2,4-difluorophenylboronic acid

: 391250-41-2
2-(2',4'-difluorophenyl)-4-methylpyridine

Conditions

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%

2-Bromo-4-methylpyridine Specification

The 2-Bromo-4-methylpyridine is an organic compound with the formula C₆H₆BrN. The IUPAC name of this chemical is 2-bromo-4-methylpyridine. With the CAS registry number 4926-28-7, it is also named as Pyridine, 2-bromo-4-methyl-. The product's categories are 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. Besides, it is colorless to orange oily liquid, which should be stored in a dark cool and dry place.

Physical properties about 2-Bromo-4-methylpyridine are: (1)ACD/LogP: 1.99; (2)ACD/LogD (pH 5.5): 1.99; (3)ACD/LogD (pH 7.4): 1.99; (4)ACD/BCF (pH 5.5): 19.2; (5)ACD/BCF (pH 7.4): 19.2; (6)ACD/KOC (pH 5.5): 288.5; (7)ACD/KOC (pH 7.4): 288.53; (8)#H bond acceptors: 1; (9)Polar Surface Area: 12.89 Å²; (10)Index of Refraction: 1.553; (11)Molar Refractivity: 36.85 cm³; (12)Molar Volume: 115.1 cm³; (13)Polarizability: 14.61×10^-24cm³; (14)Surface Tension: 40 dyne/cm; (15)Density: 1.494 g/cm³; (16)Flash Point: 86.7 °C; (17)Enthalpy of Vaporization: 43.76 kJ/mol; (18)Boiling Point: 219.8 °C at 760 mmHg; (19)Vapour Pressure: 0.173 mmHg at 25°C.

Preparation: this chemical can be prepared by 4-methyl-pyridin-2-ylamine. This reaction will need reagent NaNO₂, HBr and Br₂.

Uses of 2-Bromo-4-methylpyridine: it can be used to produce 4-methyl-2-trimethylsilanyl-pyridine at temperature of 70 °C. It will need reagent Mg, I₂ and solvent tetrahydrofuran with reaction time of 1 hour. The yield is about 73%.

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: Cc1ccnc(c1)Br
(2)InChI: InChI=1/C6H6BrN/c1-5-2-3-8-6(7)4-5/h2-4H,1H3
(3)InChIKey: LSZMVESSGLHDJE-UHFFFAOYAK
(4)Std. InChI: InChI=1S/C6H6BrN/c1-5-2-3-8-6(7)4-5/h2-4H,1H3
5)Std. InChIKey: LSZMVESSGLHDJE-UHFFFAOYSA-N

Product Name

2-Bromo-4-methylpyridine

Synthetic route

2-Bromo-4-methylpyridine Specification

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