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2732-28-7

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Basic Information

Molecular Structure:
CAS No.:	2732-28-7
Name:	1-(2-METHYLPYRIDIN-4-YL)ETHANONE
Article Data:	15

Formula:	C8H9 N O
Molecular Weight:	135.166
Synonyms:	Ketone,methyl 2-methyl-4-pyridyl (6CI,7CI,8CI); 1-(2-Methyl-4-pyridinyl)ethanone;2-Methyl-4-acetylpyridine; 4-Acetyl-2-methylpyridine
Density:	1.036g/cm³
Melting Point:	149 °C
Boiling Point:	226.8°C at 760 mmHg
Flash Point:	96.3°C
Hazard Symbols:	Xn
Risk Codes:	20/21/22-36/37
Safety:	26-36/37
PSA:	29.96000
LogP:	1.59260

Synthetic route

: 4-(1-ethoxyvinyl)-2-methylpyridine

: 2732-28-7
1-(2-methylpyridin-4-yl)ethan-1-one

Conditions	Yield
With hydrogenchloride; water at 20℃; for 3h;	82%

: 1211580-90-3
N-methoxy-N,2-dimethylisonicotinamide

: 917-54-4
methyllithium

: 2732-28-7
1-(2-methylpyridin-4-yl)ethan-1-one

Conditions	Yield
In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere;	56.4%
In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere;	56.4%
Stage #1: N-methoxy-N,2-dimethylisonicotinamide; methyllithium In tetrahydrofuran at -78 - 20℃; for 1.5h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran	51%
In tetrahydrofuran at -78 - 20℃; for 1.5h; Inert atmosphere;	51%

: 22282-99-1
4-bromo-2-methylpyridine

: 97674-02-7
tributyl(1-ethoxyvinyl)stannane

: 2732-28-7
1-(2-methylpyridin-4-yl)ethan-1-one

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In toluene at 80℃; Inert atmosphere;	44%

: 2214-53-1
2-methyl-4-cyanopyridine

: 75-16-1
methylmagnesium bromide

: 2732-28-7
1-(2-methylpyridin-4-yl)ethan-1-one

Conditions	Yield
In tetrahydrofuran; hexane at 0℃; Grignard reaction; Reflux;	25%
Stage #1: 2-methyl-4-cyanopyridine; methylmagnesium bromide In tetrahydrofuran; hexane at 0℃; Heating; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water at 20℃;	25%
Stage #1: 2-methyl-4-cyanopyridine; methylmagnesium bromide In diethyl ether at 20℃; for 16h; Stage #2: With hydrogenchloride In water

: 2214-53-1
2-methyl-4-cyanopyridine

: 2732-28-7
1-(2-methylpyridin-4-yl)ethan-1-one

Conditions	Yield
With methylmagnesium bromide In water
Product distribution / selectivity;

: 4021-11-8
2-methylisonicotinic acid

: 2732-28-7
1-(2-methylpyridin-4-yl)ethan-1-one

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 20 °C 2.1: tetrahydrofuran / 1.5 h / -78 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 20 °C 2.1: tetrahydrofuran / 1.5 h / -78 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 2 h / 20 °C 2.1: tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 12 h / 20 °C 2.1: tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere View Scheme

: 108-47-4
2,4-lutidine

: 2732-28-7
1-(2-methylpyridin-4-yl)ethan-1-one

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium permanganate / water / 14 h / 80 °C 2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 2 h / 20 °C 3.1: tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: potassium permanganate / water / 14 h / 80 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 12 h / 20 °C 3.1: tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere View Scheme

: 931-19-1
2-methylpyridine N-oxide

: 2732-28-7
1-(2-methylpyridin-4-yl)ethan-1-one

Conditions	Yield
Multi-step reaction with 2 steps 1.1: dimethyl sulfate / 16 h / 20 °C 1.2: 16 h / 20 °C 2.1: tetrahydrofuran; hexane / 0 °C / Heating; Reflux 2.2: 20 °C View Scheme

: 22282-99-1
4-bromo-2-methylpyridine

: 2732-28-7
1-(2-methylpyridin-4-yl)ethan-1-one

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0) / toluene / 16 h / 110 °C / Inert atmosphere 2: hydrogenchloride; water / 3 h / 20 °C View Scheme

: 2732-28-7
1-(2-methylpyridin-4-yl)ethan-1-one

: 1187669-34-6
2-bromo-1-(2-methylpyridin-4-yl)ethan-1-one hydrobromide

Conditions	Yield
With hydrogen bromide; bromine; acetic acid at 0 - 80℃; for 2h;	96%
With hydrogen bromide; bromine; acetic acid at 0 - 20℃;	80%
With hydrogen bromide; bromine; acetic acid at 0 - 20℃;	80%

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