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CAS No.: | 3430-23-7 |
---|---|
Name: | 3,5-Dibromo-4-methylpyridine |
Article Data: | 8 |
Molecular Structure: | |
Formula: | C6H5Br2N |
Molecular Weight: | 250.92 |
Synonyms: | 4-Picoline,3,5-dibromo- (7CI,8CI); |
Density: | 1.911 g/cm3 |
Melting Point: | 104-107 °C |
Boiling Point: | 243 °C at 760 mmHg |
Flash Point: | 100.7 °C |
Hazard Symbols: | R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.; R36/37/38:Irritating to eyes, respiratory system |
Risk Codes: | 20/21/22-36/37/38 |
Safety: | 26-36/37/39 |
PSA: | 12.89000 |
LogP: | 2.91500 |
Conditions | Yield |
---|---|
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
methyl iodide
A
3,5-dibromo-4-methyl-pyridine
B
3,5-dibromo-4-ethylpyridine
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With lithium diisopropyl amide 1.) THF, -78 deg C, 5 min; 2.) -78 deg C, 2h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
[3-(hydroxymethyl)phenyl]boronic acid
a-[3-(5-Bromo-4-methyl-pyridin-3-yl)-phenyl]-methanol
Conditions | Yield |
---|---|
79% |
3,5-dibromo-4-methyl-pyridine
N,N-dimethyl-formamide
5-bromo-4-methyl-pyridine-3-carbaldehyde
Conditions | Yield |
---|---|
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.; |
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 16h; Inert atmosphere; | 71% |
Conditions | Yield |
---|---|
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine In ethanol at 90℃; for 4h; Suzuki Coupling; Inert atmosphere; | 66% |
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Risk Statements 20/21/22-36/37/38
Safety Statements 26-36/37/39