2-Acetyl-4-methylpyridine supplier

Name
2-Acetyl-4-methylpyridine
EINECS
CAS No. 59576-26-0
Article Data12
CAS DataBase
Density 1.036 g/cm³
Solubility
Melting Point 30-34 °C(lit.)
Formula C₈H₉NO
Boiling Point 227.1 °C at 760 mmHg
Molecular Weight 135.166
Flash Point 96.5 °C
Transport Information
Appearance
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Ketone,methyl 4-methyl-2-pyridyl (6CI);1-(4-Methyl-2-pyridyl)-1-ethanone;Ethanone,1-(4-methyl-2-pyridinyl)-;4-Methyl-2-acetylpyridine;
PSA 29.96000
LogP 1.59260

Synthetic route

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

: 127-19-5
N,N-dimethyl acetamide

: 59576-26-0
2-acetyl-4-methylpyridine

Conditions

Conditions	Yield
Stage #1: 2-Bromo-4-picoline With n-butyllithium In diethyl ether; hexane at -78℃; for 0.166667 - 0.5h; Stage #2: N,N-dimethyl acetamide In diethyl ether; hexane at 20℃; for 2 - 14.5h; Product distribution / selectivity;	59%
Stage #1: 2-Bromo-4-picoline With n-butyllithium In diethyl ether; hexane at -78℃; for 0.166667h; Stage #2: N,N-dimethyl acetamide In diethyl ether; hexane at 20℃; for 14.5h;	59%
With n-butyllithium In diethyl ether; hexane	37%

: 1620-76-4
2-Cyano-4-methylpyridin

: 917-64-6
methyl magnesium iodide

: 59576-26-0
2-acetyl-4-methylpyridine

Conditions

Conditions	Yield
Stage #1: 2-Cyano-4-methylpyridin; methyl magnesium iodide In diethyl ether; benzene at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: With water; ammonium chloride In diethyl ether; benzene Inert atmosphere;	52%
With diethyl ether; benzene Behandeln des Reaktionsgemisches mit wss.Ammoniumchlorid-Loesung;

: 108-89-4
picoline

: 123-63-7
paracetaldehyde

: 59576-26-0
2-acetyl-4-methylpyridine

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; iron(II) sulfate; trifluoroacetic acid In acetonitrile for 4h; Heating;	20%

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

: 59576-26-0
2-acetyl-4-methylpyridine

: 4-Methyl-2-isovalerylpyridine

A: 59576-26-0
2-acetyl-4-methylpyridine

B: 2,2-Dimethyl-1-(4-methyl-pyridin-2-yl)-cyclopropanol

C: cis-3-Methyl-1-<2-(4-methylpyridyl)>-1-cyclobutanol

D: trans-3-Methyl-1-<2-(4-methylpyridyl)>-1-cyclobutanol

Conditions

Conditions	Yield
In tert-butyl alcohol; benzene for 5h; Irradiation;
In tert-butyl alcohol; benzene for 5h; Quantum yield; Irradiation;

...Expand

: 108-89-4
picoline

: 59576-26-0
2-acetyl-4-methylpyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 30 percent / silver nitrate, ammonium persulfate, conc. H2SO4 / H2O; CH2Cl2 / 3 h / 40 °C 2: benzene; 2-methyl-propan-2-ol / 5 h / Irradiation View Scheme

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

: 59576-26-0
2-acetyl-4-methylpyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diazonium reaction View Scheme

: 1620-76-4
2-Cyano-4-methylpyridin

: 75-16-1
methylmagnesium bromide

: 59576-26-0
2-acetyl-4-methylpyridine

Conditions

Conditions	Yield
Stage #1: 2-Cyano-4-methylpyridin; methylmagnesium bromide In tetrahydrofuran; diethyl ether at -20 - -10℃; Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at -40℃; for 0.0833333h;

: 59576-26-0
2-acetyl-4-methylpyridine

: 13846-13-4
2-aminobenzenesulfonic acid sodium salt

: C14H13N2O3S(1-)*Na(1+)

Conditions

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene; ethanol Reflux;	97%

: 98-01-1
furfural

: 59576-26-0
2-acetyl-4-methylpyridine

: C13H11NO2

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water at 20℃; for 2h;	97%

: 59576-26-0
2-acetyl-4-methylpyridine

: C8H11NO

Conditions

Conditions	Yield
Stage #1: 2-acetyl-4-methylpyridine 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;	97%

: 59576-26-0
2-acetyl-4-methylpyridine

: 5392-12-1
2-methoxy-1-naphthaldehyde

: (E)-3-(2-methoxynaphthalen-1-yl)-1-(4-methylpyridin-2-yl)prop-2-en-1-one

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; for 1h; Inert atmosphere;	96%

: 59576-26-0
2-acetyl-4-methylpyridine

: 95-92-1
oxalic acid diethyl ester

: 741288-24-4
ethyl 4-(4-methylpyridin-2-yl)-2,4-dioxobutanoate

Conditions

Conditions	Yield
With sodium ethanolate In ethanol at 20℃;	95%
Stage #1: oxalic acid diethyl ester With sodium ethanolate In ethanol at 20℃; for 0.166667h; Stage #2: 2-acetyl-4-methylpyridine In ethanol for 0.5h; Stage #3: With hydrogenchloride; water Product distribution / selectivity; more than 3 stages;	82%
Stage #1: 2-acetyl-4-methylpyridine; oxalic acid diethyl ester With sodium ethanolate In ethanol at 20 - 60℃; for 9h; Stage #2: With water In diethyl ether; ethanol Product distribution / selectivity;

: 59576-26-0
2-acetyl-4-methylpyridine

: 1563017-51-5
1-(4-methyl-1-oxido-2-pyridinyl)ethanone

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃;	88%

: 59576-26-0
2-acetyl-4-methylpyridine

: 247174-18-1
6-bromo-2-methoxynaphthalene-1-carbaldehyde

: (E)-3-(6-bromo-2-methoxynaphthalen-1-yl)-1-(4-methylpyridin-2-yl)prop-2-en-1-one

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 5 - 10℃; Inert atmosphere;	83%

: 59576-26-0
2-acetyl-4-methylpyridine

: 405-18-5
trans-2-phenylethene-1-sulfonyl fluoride

: 6-(4-methylpyridin-2-yl)-4-phenyl-3,4-dihydro-1,2-oxathiine 2,2-dioxide

Conditions

Conditions	Yield
With nickel(II) nitrate hexahydrate; potassium carbonate In acetonitrile at 20℃; for 24h;	82%

: 59576-26-0
2-acetyl-4-methylpyridine

: 75-15-0
carbon disulfide

: 75-03-6
ethyl iodide

: 170653-78-8
2-(3',3'-bis(ethylthio)-1'-oxoprop-2'-en-1'-yl)-4-methylpyridine

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran Ambient temperature;	81%

...Expand

: 59576-26-0
2-acetyl-4-methylpyridine

: 2-bromo-1-(4-methylpyridin-2-yl)ethanone hydrobromide

Conditions

Conditions	Yield
With hydrogen bromide; bromine; acetic acid at 20℃; for 2h; Inert atmosphere;	81%
With bromine In HBr-AcOH; diethyl ether; acetic acid	10.8 g (63 %)

: 59576-26-0
2-acetyl-4-methylpyridine

: 5973-71-7
3,4-dimethylbenzaldehyde

: 1-[2-(4-methyl)pyridyl]-3-(3,4-dimethylphenyl)propen-1-one

Conditions

Conditions	Yield
Stage #1: 3,4-dimethylbenzaldehyde With sodium hydroxide In ethanol; water at 20℃; Stage #2: 2-acetyl-4-methylpyridine In ethanol; water at 20℃; for 0.166667h;	81%

: 59576-26-0
2-acetyl-4-methylpyridine

: 78570-34-0
3,3-bis(methylsulfanyl)-1-pyridin-2-ylprop-2-en-1-one

: 108295-36-9
4-methyl-4'-(methylthio)-2,2':6',2"-terpyridine

Conditions

Conditions	Yield
Stage #1: 2-acetyl-4-methylpyridine With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 3,3-bis(methylsulfanyl)-1-pyridin-2-ylprop-2-en-1-one In tetrahydrofuran for 16h; Stage #3: With ammonium acetate; acetic acid In tetrahydrofuran for 4h; Heating;	77%
With potassium tert-butylate; ammonium acetate 2) AcOH, heating; Multistep reaction;

: 59576-26-0
2-acetyl-4-methylpyridine

: 13331-31-2
S-benzyldithiocarbazate

: 1599471-47-2
C16H17N3S2

Conditions

Conditions	Yield
In ethanol	74%

: 59576-26-0
2-acetyl-4-methylpyridine

: 3-(3,4,5-trimethoxyphenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde

: (Z)-1-(4-methylpyridin-2-yl)-3-(1-phenyl-3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-4-yl)prop-2-en-1-one

Conditions

Conditions	Yield
With sodium hydroxide In methanol Claisen-Schmidt Condensation; Reflux;	72%

: 59576-26-0
2-acetyl-4-methylpyridine

: 1384956-00-6
3,5-dimethyl-[1,2,3]triazolo[1,5-a]pyridine

Conditions

Conditions	Yield
Stage #1: 2-acetyl-4-methylpyridine With hydrazine hydrate In ethanol for 1h; Reflux; Stage #2: With [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 0.5h;	70%
Multi-step reaction with 2 steps 1: methanol / Cooling with ice 2: morpholine / 90 - 100 °C View Scheme
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol / 1 h / Reflux 2: [bis(acetoxy)iodo]benzene / dichloromethane / 0.5 h / 20 °C View Scheme

: 59576-26-0
2-acetyl-4-methylpyridine

: 34930-10-4
S-(2-methylbenzyl)dithiocarbazate

: C17H19N3S2

Conditions

Conditions	Yield
In ethanol; acetonitrile Heating;	70%

: 59576-26-0
2-acetyl-4-methylpyridine

: 25688-12-4
N-(2-bromophenyl)hydrazinecarbothioamide

: (E)-N-(2-bromophenyl)-2-(1-(4-methylpyridin-2-yl)ethylidene)hydrazine-1-carbothioamide

Conditions

Conditions	Yield
With acetic acid In methanol for 2h; Reflux;	69%

: 59576-26-0
2-acetyl-4-methylpyridine

: 56252-09-6
2,3-Dimethoxy-naphthalene-1-carbaldehyde

: (E)-3-(2,3-dimethoxynaphthalen-1-yl)-1-(4-methylpyridin-2-yl)prop-2-en-1-one

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 5 - 10℃; Inert atmosphere;	67%

: 110-86-1
pyridine

: 59576-26-0
2-acetyl-4-methylpyridine

: N-[(2-(4-methyl)pyridin-2'-yl)-2-oxoethyl]pyridinium iodide

Conditions

Conditions	Yield
With iodine at 20℃;	65%

: 59576-26-0
2-acetyl-4-methylpyridine

: 100-10-7
4-dimethylamino-benzaldehyde

: (E)-3-(4-(dimethylamino)phenyl)-1-(4-methylpyridin-2-yl)prop-2-en-1-one

Conditions

Conditions	Yield
With potassium hydroxide In ethanol; water at 20℃; for 3h;	62%

: 59576-26-0
2-acetyl-4-methylpyridine

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 166196-85-6
3-(dimethylamino)-1-(4-methylpyridin-2-yl)prop-2-en-1-one

Conditions

Conditions	Yield
for 20h; Heating;	61%
for 3h; Reflux; Inert atmosphere; Schlenk technique;	0.6 g

: 59576-26-0
2-acetyl-4-methylpyridine

: 1122-91-4
4-bromo-benzaldehyde

: 878007-29-5
1-(3-oxo-3-[2-(4-methylpyridyl)]propen-1-yl)-4-bromobenzene

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water at 25℃; for 1h; Claisen-Schmidt condensation;	60%

: 59576-26-0
2-acetyl-4-methylpyridine

: 920518-65-6
3-dimethyl-amino-2-methylpropenal

: 1134-35-6
4,4'-dimethyl-2,2'-bipyridines

Conditions

Conditions	Yield
With ammonium acetate; sodium hydroxide; acetic acid In tetrahydrofuran; toluene	59.7%

: 59576-26-0
2-acetyl-4-methylpyridine

: 2,5-diaminobenzenesulfonic acid sodium salt

: C22H21N4O3S(1-)*Na(1+)

Conditions

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene; ethanol Reflux;	59%

: 59576-26-0
2-acetyl-4-methylpyridine

: 78-94-4
methyl vinyl ketone

A: 1567389-02-9
8-acetyl-1-aza-7-ethylbicyclo[4.3.0]nona-2,4,6,8-tetraene

B: 1567389-18-7
8-acetyl-1-aza-7-ethyl-9-(3-oxobutyl)bicyclo[4.3.0]nona-2,4,6,8-tetraene

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In water; acetonitrile at 0℃; for 12h; Baylis-Hillman Reaction; Reflux; Overall yield = 80 %;	A 57% B 23%

...Expand

: 59576-26-0
2-acetyl-4-methylpyridine

: 620-23-5
m-tolyl aldehyde

: 4′-(3-methylphenyl)-4,4″-dimethylterpyridine

Conditions

Conditions	Yield
With ammonia; potassium hydroxide In ethanol; water at 60℃; for 24h; Kroehnke Pyridine Synthesis;	51%

: 59576-26-0
2-acetyl-4-methylpyridine

: 54884-55-8
2-methoxy-6-methyl-benzaldehyde

: (E)-3-(2-methoxy-6-methylphenyl)-1-(pyridin-2-yl)prop-2-en-1-one

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; for 1h; Inert atmosphere;	48%

: 59576-26-0
2-acetyl-4-methylpyridine

: 87199-17-5
4-formylphenylboronic acid,

: C23H20BN3O2

Conditions

Conditions	Yield
Stage #1: 2-acetyl-4-methylpyridine; 4-formylphenylboronic acid, With sodium hydroxide In ethanol at 25℃; for 10h; Stage #2: With ammonium hydroxide In ethanol; water for 20h; Reflux;	47%

2-Acetyl-4-methylpyridine Chemical Properties

Empirical Formula: C₈H₉NO
Molecular Weight: 135.1632
Freely Rotating Bonds: 1
Polar Surface Area: 29.96 Å²
Index of Refraction: 1.512
Molar Refractivity: 39.19 cm³
Molar Volume: 130.4 cm³
Polarizability: 15.53× 10^-24cm³
Surface Tension: 38.1 dyne/cm
Density: 1.036 g/cm³
Flash Point: 96.5 °C
Enthalpy of Vaporization: 46.37 kJ/mol
Melting Point: 30-34 °C(lit.)
Boiling Point: 227.1 °C at 760 mmHg
Vapour Pressure: 0.0788 mmHg at 25°C
The Cas Register Number of 2-Acetyl-4-methylpyridine is 59576-26-0.The chemical synonyms of 2-Acetyl-4-methylpyridine (CAS NO.59576-26-0) are 1-(4-Methyl-2-pyridinyl)ethanone and ethanone, 1-(4-methyl-2-pyridinyl)- .The molecular structure of 2-Acetyl-4-methylpyridine (CAS NO.59576-26-0) is
.

2-Acetyl-4-methylpyridine Uses

2-Acetyl-4-methylpyridine (CAS NO.59576-26-0) is used as organic intermediate .

2-Acetyl-4-methylpyridine Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
WGK Germany: 3

Product Name

2-Acetyl-4-methylpyridine

Synthetic route

2-Acetyl-4-methylpyridine Chemical Properties

2-Acetyl-4-methylpyridine Uses

2-Acetyl-4-methylpyridine Safety Profile

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