6940-57-4

Basic information

• Product Name: 1-(6-METHYL-PYRIDIN-2-YL)-ETHANONE
• Synonyms: 1-(6-METHYL-PYRIDIN-2-YL)-ETHANONE;2-ACETYL-6-METHYLPYRIDINE;1-(6-Methyl-2-pyridinyl)ethanone;6-Acetyl-2-methylpyridine;1-(6-Methylpyridin-2-yl)ethan-1-one;2-ACETYL-6-METHYLPYRIDINE 1-(6-METHYL-PYRIDIN-2-YL)-ETHANONE;Ethanone, 1-(6-methyl-2-pyridinyl)-;6-methyl-2-acetylpyridine
• CAS NO: 6940-57-4
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.16
• Product Categories: Pyridine series;Building Blocks;Pyridine;Pyridines
• Mol File: 6940-57-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 209℃
• Flash Point: 84°(183°F)
• Appearance: Pale yellow/Solid
• Density: 1.036 g/cm³
• Vapor Pressure: 0.208mmHg at 25°C
• Refractive Index: 1.5150
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 3.24±0.10(Predicted)
• CAS DataBase Reference: 1-(6-METHYL-PYRIDIN-2-YL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(6-METHYL-PYRIDIN-2-YL)-ETHANONE(6940-57-4)
• EPA Substance Registry System: 1-(6-METHYL-PYRIDIN-2-YL)-ETHANONE(6940-57-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36
• Hazardous Substances Data: 6940-57-4(Hazardous Substances Data)

Usage

Uses

2-Acetyl-6-methylpyridine is a flavor constituent of rum. A useful synthetic and industrial reagent.

InChI:InChI=1/C8H9NO/c1-6-4-3-5-8(9-6)7(2)10/h3-5H,1-2H3

Synthetic route

N-methoxy-N,6-dimethylpyridine-2-carboxamide (476471-33-7) + methylmagnesium bromide (75-16-1) → 2-acetyl-6-methylpyridine (6940-57-4)

Conditions	Yield
In tetrahydrofuran at -30 - 20℃; for 2h; Inert atmosphere;	100%

(+/-)-1-[2-(6-methylpyridyl)]ethanol (71777-66-7) → 2-acetyl-6-methylpyridine (6940-57-4)

Conditions	Yield
Stage #1: (+/-)-1-[2-(6-methylpyridyl)]ethanol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -75℃; for 1.33333h; Stage #2: With triethylamine In dichloromethane at -75 - 20℃; for 2h;	92%

oxalyl dichloride (79-37-8) + (+/-)-1-[2-(6-methylpyridyl)]ethanol (71777-66-7) → 2-acetyl-6-methylpyridine (6940-57-4)

Conditions	Yield
With triethylamine In dichloromethane; dimethyl sulfoxide	92%

2-bromo-6-methylpyridine (5315-25-3) + N,N-dimethyl acetamide (127-19-5) → 2-acetyl-6-methylpyridine (6940-57-4)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; diethyl ether; hexane	88%
With n-butyllithium In diethyl ether; hexane	24%
With n-butyllithium 1.) diethyl ether, hexane, THF, -78 deg C, 2.) diethyl ether, hexane, THF, 5-30 min; Multistep reaction;

N-methoxy-N,6-dimethylpyridine-2-carboxamide (476471-33-7) + methylmagnesium bromide (75-16-1) → 2-acetyl-6-methylpyridine (6940-57-4)

Conditions	Yield
In tetrahydrofuran at -30 - 20℃; for 2h; Inert atmosphere;	100%

(+/-)-1-[2-(6-methylpyridyl)]ethanol (71777-66-7) → 2-acetyl-6-methylpyridine (6940-57-4)

Conditions	Yield
Stage #1: (+/-)-1-[2-(6-methylpyridyl)]ethanol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -75℃; for 1.33333h; Stage #2: With triethylamine In dichloromethane at -75 - 20℃; for 2h;	92%

oxalyl dichloride (79-37-8) + (+/-)-1-[2-(6-methylpyridyl)]ethanol (71777-66-7) → 2-acetyl-6-methylpyridine (6940-57-4)

Conditions	Yield
With triethylamine In dichloromethane; dimethyl sulfoxide	92%

2-bromo-6-methylpyridine (5315-25-3) + N,N-dimethyl acetamide (127-19-5) → 2-acetyl-6-methylpyridine (6940-57-4)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; diethyl ether; hexane	88%
With n-butyllithium In diethyl ether; hexane	24%
With n-butyllithium 1.) diethyl ether, hexane, THF, -78 deg C, 2.) diethyl ether, hexane, THF, 5-30 min; Multistep reaction;

2-Cyano-6-methylpyridine (1620-75-3) + methylmagnesium bromide (75-16-1) → 2-acetyl-6-methylpyridine (6940-57-4)

Conditions	Yield
Stage #1: 2-Cyano-6-methylpyridine; methylmagnesium bromide In tetrahydrofuran; diethyl ether at -20 - -10℃; Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at -40℃; for 0.0833333h;	83%
In tetrahydrofuran at -20℃; for 5h;	72%

2-Cyano-6-methylpyridine (1620-75-3) + methyllithium (917-54-4) → 2-acetyl-6-methylpyridine (6940-57-4)

Conditions	Yield
In diethyl ether at -78℃; for 6h; Inert atmosphere;	78%

6-methylpicolinic acid methyl ester (13602-11-4) → 2-acetyl-6-methylpyridine (6940-57-4)

Conditions	Yield
With sodium ethanolate In ethyl acetate Acidic conditions;	68%

2-methyl-6-vinylpyridine (1122-70-9) → 2-acetyl-6-methylpyridine (6940-57-4)

Conditions	Yield
With sodium hydroxide; chlorine

β-oxo-β-<6-methyl-pyridyl-(2)>-propionic acid ethyl ester → 2-acetyl-6-methylpyridine (6940-57-4)

Conditions	Yield
With hydrogenchloride

hydrogenchloride (7647-01-0) + 3-(6-methyl-[2]pyridyl)-3-oxo-propionic acid ethyl ester; potassium-compound → 2-acetyl-6-methylpyridine (6940-57-4)

6-methyl-2-pyridinecarboxylic acid (934-60-1) → 2-acetyl-6-methylpyridine (6940-57-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: Acidic conditions 2: sodium ethanolate / ethyl acetate / Acidic conditions View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 3 h / 20 °C 2: tetrahydrofuran / 2 h / -30 - 20 °C / Inert atmosphere View Scheme

2-acetyl-6-methylpyridine (6940-57-4) → 2-bromo-1-(6-methyl-pyridin-2-yl)-ethanone hydrobromide (147097-80-1)

Conditions	Yield
With hydrogen bromide; bromine; acetic acid In dichloromethane at 20℃; for 3h; Cooling with ice;	95%
With hydrogen bromide; bromine; acetic acid for 1h;

2-acetyl-6-methylpyridine (6940-57-4) → 1-(6-methyl-1-oxido-2-pyridinyl)ethanone (1563017-55-9)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃;	94%

2-acetyl-6-methylpyridine (6940-57-4) + ethylene glycol (107-21-1) → 2-methyl-6-(2-methyl-1,3-dioxolan-2-yl)pyridine (1425936-72-6)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 8h; Dean-Stark; Reflux;	93%
With toluene-4-sulfonic acid In toluene at 20℃; for 24h; Reflux;	22 g

2-acetyl-6-methylpyridine (6940-57-4) + 4-fluorophenylhydrazine (371-14-2) → C14H14FN3 (1429087-95-5)

Conditions	Yield
In ethanol for 0.5h; Reflux;	92.5%
In ethanol for 0.5h; Reflux;	16.5 g

2-acetyl-6-methylpyridine (6940-57-4) + 2-aminobenzaldehyde (529-23-7) → 2-(6-methylpyridin-2-yl)quinoline (56100-29-9)

Conditions	Yield
With potassium hydroxide In ethanol Reflux;	92%
With potassium hydroxide In ethanol at 85℃; for 3h; Inert atmosphere;	57%
With potassium hydroxide In ethanol at 85℃; for 3h;	57%

2-acetyl-6-methylpyridine (6940-57-4) → C8H11NO

Conditions	Yield
Stage #1: 2-acetyl-6-methylpyridine With trimethylaluminum; (R)-2,2’-diphenyl-(4-biphenanthrol); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 20℃; for 2h; Glovebox; Inert atmosphere; Stage #2: With methanol for 0.5h; enantioselective reaction;	92%

2-acetyl-6-methylpyridine (6940-57-4) + (S)-1-phenyl-ethylamine (2627-86-3) → N-(1-(6-methylpyridin-2-yl)ethylidene)-11-phenylethanamine

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 48h; Reflux; Inert atmosphere;	90%

2-acetyl-6-methylpyridine (6940-57-4) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → (E)-3-(dimethylamino)-1-(6-methylpyridin-2-yl)prop-2-en-1-one (854923-64-1)

Conditions	Yield
at 110℃; for 7h;	89%
at 105℃; for 7h; Inert atmosphere;	80%

2-acetyl-6-methylpyridine (6940-57-4) + ethylene glycol (107-21-1) → 2‐bromo‐6‐(2‐methyl‐1,3‐dioxolan‐2‐yl)pyridine (49669-14-9)

Conditions	Yield
With toluene-4-sulfonic acid In benzene	88%

2-acetyl-6-methylpyridine (6940-57-4) + N-(2-bromophenyl)hydrazinecarbothioamide (25688-12-4) → (E)-N-(2-bromophenyl)-2-(1-(6-methylpyridin-2-yl)ethylidene)hydrazine-1-carbothioamide

Conditions	Yield
With acetic acid In methanol for 2h; Reflux;	85%

2-acetyl-6-methylpyridine (6940-57-4) + hydrazinecarbodithioic acid methyl ester (5397-03-5) → 3-<1-(6-Methyl-2-pyridyl)ethylidene>hydrazinecarbothioate (26155-39-5)

Conditions	Yield
In ethanol at 60℃; for 3h;	84%

2-acetyl-6-methylpyridine (6940-57-4) + N-methyl-hydrazinecarbodithioic acid methyl ester (20184-94-5) → methyl 3-<1-(6-methyl-2-pyridyl)ethylidene>methylhydrazinecarbodithioate (74752-60-6)

Conditions	Yield
With acetic acid In ethanol for 20h; Heating;	79%

2-acetyl-6-methylpyridine (6940-57-4) + 6-chloroquinoline (612-57-7) → 1-(6-methylpyridin-2-yl)-2-(quinolin-6-yl)ethanone (476472-48-7)

Conditions	Yield
Stage #1: 2-acetyl-6-methylpyridine; 6-chloroquinoline With potassium tert-butylate; palladium diacetate; DavePhos In tetrahydrofuran at 80℃; for 18h; Stage #2: With acetic acid In tetrahydrofuran at 20℃;	78%
With potassium tert-butylate; palladium diacetate; DavePhos In tetrahydrofuran at 80℃; Inert atmosphere;	75%
With potassium tert-butylate; palladium diacetate; DavePhos In tetrahydrofuran at 75℃; for 14h;	75%

2-acetyl-6-methylpyridine (6940-57-4) + 6-chloroquinoline (612-57-7) + DavePhos (213697-53-1) → 1-(6-methylpyridin-2-yl)-2-(quinolin-6-yl)ethanone (476472-48-7)

Conditions	Yield
With potassium tert-butylate; acetic acid; palladium diacetate In tetrahydrofuran	78%

2-acetyl-6-methylpyridine (6940-57-4) + 3-(3,4,5-trimethoxyphenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde → (Z)-1-(6-methylpyridin-2-yl)-3-[1-phenyl-3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-4-yl]prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In methanol Claisen-Schmidt Condensation; Reflux;	78%

2-acetyl-6-methylpyridine (6940-57-4) + 2-(2-aminophenyl)-1H-indole (32566-01-1) → [2-(1H-indol-2-yl)phenyl]-[1-(6-methyl-pyridin-2-yl)ethylidene]amine (1331843-80-1)

Conditions	Yield
With acetic acid In ethanol for 3h; Reflux;	75%

2-acetyl-6-methylpyridine (6940-57-4) + 2-methylthioaniline → N-[1-(6-methylpyridin-2-yl)ethylidene]-2-(methylthio)aniline

Conditions	Yield
With acetic acid; aniline; zinc(II) chloride for 2h; Reflux;	75%

2-acetyl-6-methylpyridine (6940-57-4) + 6-methylpicolinic acid methyl ester (13602-11-4) → 1,3-bis-(6-methyl-pyridin-2-yl)-propane-1,3-dione (93733-12-1)

Conditions	Yield
With sodium ethanolate In toluene	75%

2-acetyl-6-methylpyridine (6940-57-4) → 2-bromo-1-(6-methylpyridin-2-yl)ethan-1-one (88625-09-6)

Conditions	Yield
With hydrogen bromide; bromine; acetic acid at 0 - 20℃; for 1h;	75%

2-acetyl-6-methylpyridine (6940-57-4) + 2-amino-5-bromobenzophenone (39859-36-4) → 4-phenyl-6-bromo-2-(2'-(6'-methyl)pyridinyl)quinoline

Conditions	Yield
With phosphorus pentaoxide In various solvent(s) at 135℃; Friedlander reaction;	71%

2-acetyl-6-methylpyridine (6940-57-4) + 1,3-bis(4-methylphenyl)prop-2-yn-1-one (97691-66-2) → (4′-methyl-3,5-bis(6-methylpyridin-2-yl)-[1,1′-biphenyl]-2-yl)(p-tolyl)methanone

Conditions	Yield
With [2,2]bipyridinyl; cobalt(II) bromide; zinc In 1,4-dioxane at 140℃; Sealed tube; Inert atmosphere; regioselective reaction;	71%

2-acetyl-6-methylpyridine (6940-57-4) + [(2-methylpropane-1,3-diyl)bis(oxy)]diammonium dibromide → 1-(6-methylpyridin-2-yl)ethanone O,O'-(2-methylpropane-1,3-diyl)oxime (1034419-32-3)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol for 4h; Product distribution / selectivity; Heating; Reflux;	70%

2-acetyl-6-methylpyridine (6940-57-4) + anthranilic acid nitrile (1885-29-6) → 2-[[1-(6-methylpyridin-2-yl)ethylidene]amino]benzonitrile

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating / reflux;	67.6%

Upstream product

• 5315-25-3 2-bromo-6-methylpyridine 
• 127-19-5 N,N-dimethyl acetamide 
• 7647-01-0 hydrogenchloride 
• 79-37-8 oxalyl dichloride 
• 71777-66-7 (+/-)-1-[2-(6-methylpyridyl)]ethanol 
• 1620-75-3 2-Cyano-6-methylpyridine 
• 917-54-4 methyllithium 
• 934-60-1 6-methyl-2-pyridinecarboxylic acid 
• 13602-11-4 6-methylpicolinic acid methyl ester 
• 476471-33-7 N-methoxy-N,6-dimethylpyridine-2-carboxamide 
• 75-16-1 methylmagnesium bromide 
• 1122-70-9 2-methyl-6-vinylpyridine 

Downstream Products

• 676476-21-4 (R)-(6-methylpyridin-2-yl)ethan-1-ol 
• 58088-67-8 1-(6-methylpyridin-2-yl)ethan-1-amine 
• 1308760-98-6 2-(5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-pyrazol-1-yl)-N-phenylacetamide 
• 1308760-89-5 2-(3-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-pyrazol-1-yl)-N-phenylacetamide 
• 1308760-99-7 N-(3-cyanophenyl)-2-(5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-pyrazol-1-yl)acetamide 
• 1308760-90-8 N-(3-cyanophenyl)-2-(3-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-pyrazol-1-yl)acetamide 
• 1308761-00-3 2-(4-(4-methoxyquinolin-6-yl-)-5-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl)-N-phenylacetamide 
• 1308760-92-0 2-(4-(4-methoxyquinolin-6-yl)-3-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl)-N-phenylacetamide 
• 1308761-02-5 N-(3-cyanophenyl)-2-(4-(4-methoxyquinolin-6-yl)-5-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl)acetamide 
• 1308760-93-1 N-(3-cyanophenyl)-2-(4-(4-methoxyquinolin-6-yl)-3-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl)acetamide 
• 1308760-95-3 3-(2-(3-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-pyrazol-yl)-1H-pyrazol-acetamido)benzamide 
• 1308761-05-8 3-(2-(5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-pyrazol-1-yl)acetamido)benzamide 
• 1308761-07-0 3-(3-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-pyrazol-1-yl)-N-phenylpropanamide 
• 1308761-08-1 N-(3-cyanophenyl)-3-(3-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-pyrazol-1-yl)propanamide 

Relevant articles and documents

ADENOSINE RECEPTOR BINDING COMPOUNDS

The present invention relates to pharmaceutical compounds and compositions of Formula (I) and methods of treatment using the compounds and compositions, especially for the treatment and/or prevention of a proliferation disorder, such as cancer. Compounds of Formula (I) as further described herein are shown modulators of the adenosine A2A receptor and exhibit antiproliferative activity. Accordingly, these compounds are useful to treat proliferative disorders such as cancer, and other adenosine receptor-related conditions including an inflammatory disease, renal disease, diabetes, vascular disease, lung disease, or an autoimmune disease.

NOVEL MORPHOLINE DERIVATIVE OR SALT THEREOF

There is provided a morpholine derivative represented by General Formula [1A] or a salt thereof. (In the formula, a ring A represents a ring represented by General Formula [I]; * represents a bonding position; Z2 represents CH or the like; Z1 represents CR6 or the like; R6 represents a hydrogen atom or the like; X1 represents CHR7 or the like; R7 represents a hydrogen atom or the like; X2 represents CH2 or the like; R1 and R2 are the same as or different from each other, and each of R1 and R2 represents a hydrogen atom or the like; R3, R4, and R5 are the same as or different from each other, and each of R3, R4, and R5 represents a hydrogen atom, NRaRb, or the like; and each of Ra and Rb represents a hydrogen atom, a C1-8 alkyl group which may have a substituent, or the like.)

A two-in-one pincer ligand and its diiron(II) complex showing spin state switching in solution through reversible ligand exchange

A novel pyrazolate-bridged ligand providing two {PNN} pincer-type compartments has been synthesized. Its diiron(II) complex LFe2(OTf)3(CH3CN) (1; Tf=triflate) features, in solid state, two bridging triflate ligands, with a terminal triflate and a MeCN ligand completing the octahedral coordination spheres of the two high-spin metalions. In MeCN solution, 1 is shown to undergo a sequential, reversible, and complete spin transition to the low-spin state upon cooling. Detailed UV/Vis and 19F NMR spectroscopic studies as well as magnetic measurements have unraveled that spin state switching correlates with a rapid multistep triflate/MeCN ligand exchange equilibrium. The spin transition temperature can be continuously tuned by varying the triflate concentration in solution.