Product Name

  • Name

    3,5-Dibromo-4-methylpyridine

  • EINECS
  • CAS No. 3430-23-7
  • Article Data8
  • CAS DataBase
  • Density 1.911 g/cm3
  • Solubility
  • Melting Point 104-107 °C
  • Formula C6H5Br2N
  • Boiling Point 243 °C at 760 mmHg
  • Molecular Weight 250.92
  • Flash Point 100.7 °C
  • Transport Information
  • Appearance
  • Safety 26-36/37/39
  • Risk Codes 20/21/22-36/37/38
  • Molecular Structure Molecular Structure of 3430-23-7 (3,5-Dibromo-4-methylpyridine)
  • Hazard Symbols R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.; R36/37/38:Irritating to eyes, respiratory system
  • Synonyms 4-Picoline,3,5-dibromo- (7CI,8CI);
  • PSA 12.89000
  • LogP 2.91500

Synthetic route

3,5-dibromopyridine
625-92-3

3,5-dibromopyridine

methyl iodide
74-88-4

methyl iodide

3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

Conditions
ConditionsYield
Stage #1: 3,5-dibromopyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran at -78 - 20℃; for 18h;		66%
Stage #1: 3,5-dibromopyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - -10℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #1: 3,5-dibromopyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃;
Stage #2: methyl iodide In tetrahydrofuran at -78℃;
3,5-dibromopyridine
625-92-3

3,5-dibromopyridine

methyl iodide
74-88-4

methyl iodide

A

3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

B

3,5-dibromo-4-ethylpyridine
125419-80-9

3,5-dibromo-4-ethylpyridine

Conditions
ConditionsYield
With lithium diisopropyl amide 1.) THF, -78 deg C, 5 min; 2.) THF, -78 deg C, excess MeI; Yield given. Multistep reaction. Yields of byproduct given;
...Expand
3,5-dibromopyridine
625-92-3

3,5-dibromopyridine

methyl iodide
74-88-4

methyl iodide

A

3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

B

3,5,3',5'-Tetrabromo-1,4-dihydro-[4,4']bipyridinyl

3,5,3',5'-Tetrabromo-1,4-dihydro-[4,4']bipyridinyl

Conditions
ConditionsYield
With lithium diisopropyl amide 1.) THF, -78 deg C, 5 min; 2.) -78 deg C, 2h; Yield given. Multistep reaction;
...Expand
methyl iodide
74-88-4

methyl iodide

3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

Conditions
ConditionsYield
Stage #1: 3,5-dibromopyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - -10℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; for 2h;
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

C8H7Br2NO2

C8H7Br2NO2

Conditions
ConditionsYield
Stage #1: 3,5-dibromo-4-methyl-pyridine With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Stage #2: carbonic acid dimethyl ester In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;		93%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

2.3-dihydro-1,4-benzodioxin-6-ylboronic acid

2.3-dihydro-1,4-benzodioxin-6-ylboronic acid

C14H12BrNO2

C14H12BrNO2

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 85℃; for 16h; Inert atmosphere;80%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

[3-(hydroxymethyl)phenyl]boronic acid
87199-15-3

[3-(hydroxymethyl)phenyl]boronic acid

a-[3-(5-Bromo-4-methyl-pyridin-3-yl)-phenyl]-methanol
351458-12-3

a-[3-(5-Bromo-4-methyl-pyridin-3-yl)-phenyl]-methanol

Conditions
ConditionsYield
79%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

5-bromo-4-methyl-pyridine-3-carbaldehyde
351457-86-8

5-bromo-4-methyl-pyridine-3-carbaldehyde

Conditions
ConditionsYield
Stage #1: 3,5-dibromo-4-methyl-pyridine With n-butyllithium In tetrahydrofuran; hexane at -100℃; for 0.0833333h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -100 - -78℃; for 1.33333h;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water Saturated solution;		72%
Stage #1: 3,5-dibromo-4-methyl-pyridine With n-butyllithium at -78℃;
Stage #2: N,N-dimethyl-formamide Further stages.;
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

phenylboronic acid
98-80-6

phenylboronic acid

C12H10BrN

C12H10BrN

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 16h; Inert atmosphere;71%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

potassium vinyltrifluoroborate

potassium vinyltrifluoroborate

C8H8BrN

C8H8BrN

Conditions
ConditionsYield
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine In ethanol at 90℃; for 4h; Suzuki Coupling; Inert atmosphere;66%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

3,5-diiodo-4-methyl-pyridine
98139-01-6

3,5-diiodo-4-methyl-pyridine

Conditions
ConditionsYield
With copper(l) iodide; potassium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 130℃; for 16h;65%
With copper(l) iodide; potassium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 16h; Inert atmosphere;
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane Reflux;
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

1-[4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)phenyl]pyrrolidin-2-one
1003309-09-8

1-[4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)phenyl]pyrrolidin-2-one

1-(4-(5-bromo-4-methylpyridin-3-yl)phenyl)pyrrolidin-2-one

1-(4-(5-bromo-4-methylpyridin-3-yl)phenyl)pyrrolidin-2-one

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 85℃; for 3h; Inert atmosphere;63%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

Ethyl isobutyrate
97-62-1

Ethyl isobutyrate

1-(3,5-dibromopyridin-4-yl)-3-methylbutan-2-one

1-(3,5-dibromopyridin-4-yl)-3-methylbutan-2-one

Conditions
ConditionsYield
Stage #1: 3,5-dibromo-4-methyl-pyridine With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 1.16667h; Inert atmosphere;
Stage #2: Ethyl isobutyrate In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;		63%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

carbon dioxide
124-38-9

carbon dioxide

5-bromo-4-methylpyridine-3-carboxylic acid
677702-58-8

5-bromo-4-methylpyridine-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: 3,5-dibromo-4-methyl-pyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: carbon dioxide In tetrahydrofuran; hexane at -78 - 20℃; for 1h;		53%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

methylamine
74-89-5

methylamine

5-bromo-N,4-dimethylpyridin-3-amine

5-bromo-N,4-dimethylpyridin-3-amine

Conditions
ConditionsYield
With copper In 1,4-dioxane at 100℃; for 5h;50%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

5-bromo-4-methylnicotinonitrile
890092-52-1

5-bromo-4-methylnicotinonitrile

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; palladium diacetate; sodium hydride; 1,2-bis-(diphenylphosphino)ethane; potassium iodide In N,N-dimethyl-formamide at 130℃; for 22h; Inert atmosphere;48%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

tert-butyl 4-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]piperazine-1-carboxylate
470478-90-1

tert-butyl 4-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]piperazine-1-carboxylate

tert-butyl 4-(4-(5-bromo-4-methylpyridin-3-yl)phenyl)piperazine-1-carboxylate

tert-butyl 4-(4-(5-bromo-4-methylpyridin-3-yl)phenyl)piperazine-1-carboxylate

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate monohydrate In 1,4-dioxane; water at 85℃; Suzuki-Miyaura Coupling;47%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

3-bromo-5-(4-methoxyphenyl)-4-methylpyridine
885681-79-8

3-bromo-5-(4-methoxyphenyl)-4-methylpyridine

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 80℃; for 4h;46%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline
1021868-08-5

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

5-(5-bromo-4-methylpyridin-3-yl)quinoline

5-(5-bromo-4-methylpyridin-3-yl)quinoline

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere;41.2%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

2-(3-ethoxy-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(3-ethoxy-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

3-bromo-5-(3-ethoxy-4-methoxyphenyl)-4-methylpyridine

3-bromo-5-(3-ethoxy-4-methoxyphenyl)-4-methylpyridine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; potassium carbonate In 1,4-dioxane; water at 120℃; for 2h; Inert atmosphere;35%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

ethyl bromoacetate
105-36-2

ethyl bromoacetate

ethyl 3-(3,5-dibromopyridin-4-yl)propanoate
1440520-08-0

ethyl 3-(3,5-dibromopyridin-4-yl)propanoate

Conditions
ConditionsYield
Stage #1: 3,5-dibromo-4-methyl-pyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: ethyl bromoacetate In tetrahydrofuran at -78℃; for 3h;		33.5%
Stage #1: 3,5-dibromo-4-methyl-pyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: ethyl bromoacetate In tetrahydrofuran at -78℃; for 2.5h; Inert atmosphere;		33%
Stage #1: 3,5-dibromo-4-methyl-pyridine With lithium diisopropyl amide In tetrahydrofuran at -78 - -70℃; for 0.5h; Inert atmosphere;
Stage #2: ethyl bromoacetate In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere;		32%
Stage #1: 3,5-dibromo-4-methyl-pyridine With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - -70℃; for 0.5h; Inert atmosphere;
Stage #2: ethyl bromoacetate In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere;		32%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

tetramethylstannane
594-27-4

tetramethylstannane

3,4,5-trimethylpyridine
20579-43-5

3,4,5-trimethylpyridine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride In toluene for 18h; Heating;33%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

5-methylisoindolin-1-one
65399-03-3

5-methylisoindolin-1-one

2-(5-bromo-4-methylpyridin-3-yl)-5-methylisoindolin-1-one
1231891-05-6

2-(5-bromo-4-methylpyridin-3-yl)-5-methylisoindolin-1-one

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine In 1,4-dioxane at 100℃; for 15h;30%
trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

3-bromo-4-methyl-5-(prop-1-ynyl)pyridine
1383985-19-0

3-bromo-4-methyl-5-(prop-1-ynyl)pyridine

Conditions
ConditionsYield
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 70℃; Inert atmosphere;16%
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

butyraldehyde
123-72-8

butyraldehyde

1-(5-Bromo-4-methyl-pyridin-3-yl)-butan-1-ol

1-(5-Bromo-4-methyl-pyridin-3-yl)-butan-1-ol

Conditions
ConditionsYield
With n-butyllithium 1.) THF, -100 deg C, 4 min; 2.) 1 h, -78 deg C; Yield given. Multistep reaction;
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

5-[3-[4-methoxymethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-4-methyl-pyridine-3-carbaldehyde
916326-88-0

5-[3-[4-methoxymethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-4-methyl-pyridine-3-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: n-BuLi / -78 °C
2: 69 percent / Pd(PPh3)4 / 90 °C
View Scheme
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

C36H53N7O3Si2

C36H53N7O3Si2

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: n-BuLi / -78 °C
2: 69 percent / Pd(PPh3)4 / 90 °C
3: 99 percent / NaBH4
View Scheme
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

ethyl-{5-[3-(4-methoxymethyl-1H-benzoimidazol-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-4-methyl-pyridin-3-ylmethyl}-amine

ethyl-{5-[3-(4-methoxymethyl-1H-benzoimidazol-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-4-methyl-pyridin-3-ylmethyl}-amine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: n-BuLi / -78 °C
2: 69 percent / Pd(PPh3)4 / 90 °C
3: 99 percent / NaBH4
4: 38 percent / aq. HCl / ethanol
View Scheme
3,5-dibromo-4-methyl-pyridine
3430-23-7

3,5-dibromo-4-methyl-pyridine

2-{4-[1-(3,4-bis-difluoromethoxy-phenyl)-2-(3,5-dimethyl-pyridin-4-yl)-ethyl]-phenyl}-1,1,1,3,3,3-hexafluoro-propan-2-ol

2-{4-[1-(3,4-bis-difluoromethoxy-phenyl)-2-(3,5-dimethyl-pyridin-4-yl)-ethyl]-phenyl}-1,1,1,3,3,3-hexafluoro-propan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 33 percent / PdCl2(PPh3)2 / toluene / 18 h / Heating
2.1: LDA; HMPA / tetrahydrofuran / 0.5 h / -78 °C
2.2: 28 percent / HMPA / tetrahydrofuran / 3 h / -78 °C
3.1: TBAF / tetrahydrofuran / 6 h / 65 °C
View Scheme

3,5-Dibromo-4-methylpyridine Chemical Properties

The molecular formula of 3,5-Dibromo-4-methylpyridine(3430-23-7) is C6H5Br2N  and its formula weight is 250.92.
3,5-Dibromo-4-methylpyridine(3430-23-7) has a  melting point of  104-107°C.
The chemical synonyms of 3,5-Dibromo-4-methylpyridine(3430-23-7) are 3,5-Dibromo-4-picoline;4-Methyl-3,5-dibromopyridine;3,5-DIBROMO-4-METHYLPYRIDINE
The molecular structure of 3,5-Dibromo-4-methylpyridine(3430-23-7):

3,5-Dibromo-4-methylpyridine Safety Profile

Risk Statements  20/21/22-36/37/38
Safety Statements  26-36/37/39

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