2,5-dibromopyridine
N,N-dimethyl acetamide
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
With n-butyllithium In hexane; toluene at -40 - 20℃; for 2h; Inert atmosphere; | 100% |
Stage #1: 2,5-dibromopyridine With n-butyllithium In hexane; toluene at -40℃; for 0.666667h; Stage #2: N,N-dimethyl acetamide In hexane; toluene at 20℃; for 1h; Further stages.; | 83% |
Stage #1: 2,5-dibromopyridine With n-butyllithium In toluene Inert atmosphere; Stage #2: N,N-dimethyl acetamide In toluene Inert atmosphere; | 83% |
N,N-dimethyl acetamide
2-iodo-5-bromopyridine
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
Stage #1: 2-iodo-5-bromopyridine With n-butyllithium In hexane; toluene at -40℃; for 1h; Stage #2: N,N-dimethyl acetamide In hexane; toluene at -40 - 20℃; for 1h; | 91% |
5-bromo-N-methyoxy-N-methylpyridine-2-carboxamide
methylmagnesium chloride
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 1h; | 90% |
3-bromo-6-(trimethylsilylethynyl)pyridine
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
With sulfuric acid; mercury(II) diacetate In water; acetone for 1h; Heating; | 80% |
methylmagnesium bromide
2-Cyano-5-bromopyridine
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
Stage #1: methylmagnesium bromide; 2-Cyano-5-bromopyridine In tetrahydrofuran at -20 - -10℃; for 3h; Stage #2: With hydrogenchloride In tetrahydrofuran at -35℃; for 0.166667h; Further stages.; | 65% |
Stage #1: methylmagnesium bromide; 2-Cyano-5-bromopyridine In tetrahydrofuran at -20 - -10℃; for 3h; Stage #2: With hydrogenchloride; water In tetrahydrofuran at -40 - -35℃; for 0.166667h; | 65% |
Stage #1: methylmagnesium bromide; 2-Cyano-5-bromopyridine In tetrahydrofuran at -20 - -10℃; for 3h; Stage #2: With hydrogenchloride; water In tetrahydrofuran at -40 - -35℃; for 0.166667h; Stage #3: In tetrahydrofuran; water pH=7; potassium phosphate buffer; | 65% |
2,5-dibromopyridine
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 65 percent / NaCN / dimethylformamide / 3 h / Heating 2: tetrahydrofuran / 2 h / -20 °C View Scheme |
methylmagnesium chloride
2-Cyano-5-bromopyridine
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
Stage #1: methylmagnesium chloride; 2-Cyano-5-bromopyridine In tetrahydrofuran at -20℃; for 2h; Stage #2: With water; ammonium chloride In tetrahydrofuran | |
Stage #1: methylmagnesium chloride; 2-Cyano-5-bromopyridine In tetrahydrofuran at -20℃; for 2h; Stage #2: With water; ammonium chloride In tetrahydrofuran |
5-bromoisonicotinic acid
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 48 h / 18 - 25 °C 2: tetrahydrofuran / 1 h / -78 °C View Scheme | |
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C 2: tetrahydrofuran / 1 h / 0 - 20 °C View Scheme |
5-bromo-2-(N-methylaminocarbonyl)pyridine
methyllithium
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; for 1h; |
2-iodo-5-bromopyridine
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: isopropylmagnesium bromide / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice 1.2: 0.5 h / 20 °C / Cooling with ice 2.1: manganese(IV) oxide / dichloromethane / 40 °C View Scheme |
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
With manganese(IV) oxide In dichloromethane at 40℃; | 7.39 g |
methylmagnesium chloride
1-(5-bromopyridin-2-yl)ethanone
2-(5-bromopyridin-2-yl)propan-2-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 1h; | 100% |
In tetrahydrofuran at 0 - 20℃; for 12h; | 86% |
4-methoxyphenylboronic acid
1-(5-bromopyridin-2-yl)ethanone
1-(5-(4-methoxyphenyl)pyridin-2-yl)ethanone
Conditions | Yield |
---|---|
With potassium carbonate In ethanol; water at 90℃; for 1h; Suzuki Coupling; Microwave irradiation; | 95% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 105℃; Suzuki reaction; Inert atmosphere; | 90% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 6h; Inert atmosphere; | 88% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 70℃; for 5h; Inert atmosphere; | 88% |
3-methyl-3-(tetrahydro-2H-pyran-2-yloxy)butyne
1-(5-bromopyridin-2-yl)ethanone
1-(5-(3-methyl-3-(THP-2-yloxy)but-1-ynyl)pyridin-2-yl)ethanone
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) at 50℃; for 10h; Sonogashira reaction; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene at 105℃; for 12h; Stille reaction; Inert atmosphere; | 94% |
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
Stage #1: 1-(5-bromopyridin-2-yl)ethanone With bis(acetylacetonate)nickel(II); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) In isopropyl alcohol for 0.333333h; Inert atmosphere; Schlenk technique; Stage #2: tert-butyl α-phenyl β-nitroacrylate In isopropyl alcohol at 20℃; for 12h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 94% |
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate at 20℃; for 0.166667h; | 91.9% |
With sodium tetrahydroborate; ethanol at 20℃; for 24h; Concentration; Time; | 90% |
With sodium tetrahydroborate; ethanol at 20℃; for 24h; Concentration; | 90% |
With methanol; sodium tetrahydroborate at 0 - 25℃; for 2h; | |
With methanol; sodium tetrahydroborate at 20℃; |
1-(5-bromopyridin-2-yl)ethanone
6-bromo-3-methyl-[1,2,3]triazolo[1,5-a]pyridine
Conditions | Yield |
---|---|
With hydrazine hydrate In methanol for 3h; Reflux; | 91% |
Stage #1: 1-(5-bromopyridin-2-yl)ethanone With hydrazine hydrate In ethanol for 1h; Reflux; Stage #2: With [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 0.5h; | 71% |
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
Stage #1: 1-(5-bromopyridin-2-yl)ethanone With trimethylaluminum; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; 3,3'-bis-(3,5-bis-trifluoromethyl-phenyl)-[1,1']binaphthalenyl-2,2'-diol In toluene at 20℃; for 2h; Glovebox; Inert atmosphere; Stage #2: With methanol for 0.5h; enantioselective reaction; | 91% |
With [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I); formic acid; triethylamine In dichloromethane at 20 - 30℃; |
bis(pinacol)diborane
1-(5-bromopyridin-2-yl)ethanone
1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaboralan-2-yl)pyridin-2-yl)ethan-1-one
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane for 4h; Inert atmosphere; Reflux; | 90% |
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 100℃; for 2.5h; | |
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; | |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; |
(trifluoromethyl)trimethylsilane
1-(5-bromopyridin-2-yl)ethanone
2-(5-bromo-2-pyridinyl)-1,1,1-trifluoro-2-propanol
Conditions | Yield |
---|---|
Stage #1: (trifluoromethyl)trimethylsilane; 1-(5-bromopyridin-2-yl)ethanone With cesium fluoride In 1,2-dimethoxyethane at 0℃; for 2.5h; Stage #2: With tetrabutyl ammonium fluoride In 1,2-dimethoxyethane at 20℃; for 2.5h; | 90% |
diethylzinc
1-(5-bromopyridin-2-yl)ethanone
1-(5-ethyl-2-pyridinyl)ethanone
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 50℃; for 1h; Inert atmosphere; | 88% |
palladium bis[bis(diphenylphosphino)ferrocene] dichloride In 1,4-dioxane; hexane at 50℃; Inert atmosphere; |
ethylene glycol
1-(5-bromopyridin-2-yl)ethanone
5-bromo-2-(2-methyl-1,3-dioxolan-2-yl)pyridine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 3h; Heating; | 86% |
With aniline; toluene-4-sulfonic acid for 3h; Heating; | |
With aniline; toluene-4-sulfonic acid for 3h; Heating; |
4-nitrophenylboronic acid
1-(5-bromopyridin-2-yl)ethanone
1-(5-(4-nitrophenyl)pyridin-2-yl)ethanone
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 6h; Inert atmosphere; | 86% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene Suzuki reaction; Inert atmosphere; Heating; | 100 mg |
1-(5-bromopyridin-2-yl)ethanone
1-(5-(3,5-bis(trifluoromethyl)phenyl)pyridin-2-yl)ethanone
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 105℃; for 12h; Suzuki reaction; Inert atmosphere; | 85% |
2-[3,5-bis(1,1-dimethylethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1-(5-bromopyridin-2-yl)ethanone
2-acetyl-5-[3,5-bis(1,1-dimethylethyl)phenyl]pyridine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 85℃; Inert atmosphere; | 84% |
trimethylsilylacetylene
1-(5-bromopyridin-2-yl)ethanone
1-(5-((trimethylsilyl)ethynyl)pyridin-2-yl)ethanone
Conditions | Yield |
---|---|
With bis(benzonitrile)palladium(II) dichloride; copper diacetate; diisopropylamine; triphenylphosphine at 80℃; for 4h; Sonogashira reaction; Inert atmosphere; | 84% |
2-methyl-but-3-yn-2-ol
1-(5-bromopyridin-2-yl)ethanone
1-(5-(3-methyl-1-butyn-3-ol-1-yl)pyridin-2-yl)ethanone
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) at 50℃; for 10h; Sonogashira reaction; Inert atmosphere; | 83% |
phenylboronic acid
1-(5-bromopyridin-2-yl)ethanone
1-(5-phenylpyridin-2-yl)ethanone
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 105℃; Suzuki reaction; Inert atmosphere; | 81% |
2-cyanopyridine-5-boronic acid pinacol ester
1-(5-bromopyridin-2-yl)ethanone
6'-acetyl-[3,3‘-bipyridine]-6-carbonitrile
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 75 - 80℃; for 6h; Inert atmosphere; | 80% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 80℃; for 16h; Inert atmosphere; | 77% |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 0℃; for 4h; | 75% |
With sodium hydroxide In methanol at 0℃; for 5h; | 75% |
4-Hydroxyacetophenone
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
With potassium phosphate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; [nickel(II) (4,4'-di-tert-butyl-2,2'-bipyridine)(bromide)2] at 25℃; for 36h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation; | 75% |
furan-3-boronic acid
1-(5-bromopyridin-2-yl)ethanone
1-(5-(furan-3-yl)pyridin-2-yl)ethanone
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 4h; Inert atmosphere; | 74% |
(3R,3aS)-3-(hydroxymethyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3a,4-dihydro-1H,3H-benzo[b]oxazolo[3,4-d][1,4]oxazin-1-one
1-(5-bromopyridin-2-yl)ethanone
(3R,3aS)-7-(6-acetylpyridin-3-yl)-3-(hydroxylmethyl)-3a,4-dihydrobenzo [b]oxazolo[3,4-d][1,4]oxazin-1(3H)-one
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere; | 72% |
4-fluoroboronic acid
1-(5-bromopyridin-2-yl)ethanone
1-(5-(4-fluorophenyl)pyridin-2-yl)ethanone
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 75 - 80℃; for 6h; Inert atmosphere; | 66% |
ammonium carbonate
1-(5-bromopyridin-2-yl)ethanone
Conditions | Yield |
---|---|
In ethanol; water at 55℃; for 18h; Bucherer-Bergs Reaction; | 66% |
Empirical Formula: C7H6BrNO
Molecular Weight: 200.0326
Nominal Mass: 199 Da
Average Mass: 200.0326 Da
Monoisotopic Mass: 198.963269 Da
Index of Refraction: 1.558
Molar Refractivity: 42.06 cm3
Molar Volume: 130.3 cm3
Surface Tension: 44.6 dyne/cm
Density: 1.534 g/cm3
Flash Point: 109.4 °C
Enthalpy of Vaporization: 49.48 kJ/mol
Boiling Point: 257.2 °C at 760 mmHg
Vapour Pressure: 0.0147 mmHg at 25 °C
Structure of 2-Acetyl-5-bromopyridine (CAS NO.214701-49-2):
Product Category of 2-Acetyl-5-bromopyridine (CAS NO.214701-49-2): API intermediates;Pyridines
2-Acetyl-5-bromopyridine , its cas register number is 214701-49-2. It also can be called 1-(5-Brom-2-pyridinyl)ethanon ; 1-(5-Bromo-2-pyridinyl)ethanone ; and 5-Bromo-2-acetylpyridine .
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