7516-31-6

Basic information

• Product Name: 2,6-dimethyl-1H-pyridin-4-one
• Synonyms: 2,6-dimethyl-1H-pyridin-4-one;4(1H)-Pyridinone, 2,6-dimethyl-;4(1H)-Pyridinone,2,6-dimethyl;2,6-diMethyl-4(1H)-Pyridinone;2,6-DiMethylpyridin-4(1H)-one
• CAS NO: 7516-31-6
• Molecular Formula: C₇H₉NO
• Molecular Weight: 123.15
• Mol File: 7516-31-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 225 °C
• Boiling Point: 220-225 °C(Press: 30 Torr)
• Appearance: /
• Density: 1.013±0.06 g/cm3(Predicted)
• PKA: 12.25±0.69(Predicted)
• CAS DataBase Reference: 2,6-dimethyl-1H-pyridin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-dimethyl-1H-pyridin-4-one(7516-31-6)
• EPA Substance Registry System: 2,6-dimethyl-1H-pyridin-4-one(7516-31-6)

Safety Data

• Hazardous Substances Data: 7516-31-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 27, p. 379, 1971 DOI: 10.1016/S0040-4020(01)90708-2

Upstream product

• 591-78-6 n-hexan-2-one 
• 100-58-3 phenylmagnesium bromide 
• 78526-27-9 4'-Butylsulfanyl-2,6-dimethyl-4'H-[1,1']bipyridinyl-4-one 
• 76639-06-0 2,6-Dimethyl-4'-(2-oxo-propyl)-4'H-[1,1']bipyridinyl-4-one 
• 78526-28-0 4'-Cyclohexylsulfanyl-2,6-dimethyl-4'H-[1,1']bipyridinyl-4-one 
• 71831-53-3 4'-(3,3-Dimethyl-2-oxo-butyl)-2,6-dimethyl-4'H-[1,1']bipyridinyl-4-one 
• 78526-31-5 2,6-Dimethyl-4'-phenylsulfanyl-4'H-[1,1']bipyridinyl-4-one 
• 71831-52-2 2,6-Dimethyl-4'-(4-methyl-2-oxo-pentyl)-4'H-[1,1']bipyridinyl-4-one 
• 79756-96-0 (2',6'-Dimethyl-4'-oxo-4H,4'H-[1,1']bipyridinyl-4-yl)-acetic acid ethyl ester 
• 71831-63-5 4'-Benzylsulfanyl-2,6-dimethyl-4'H-[1,1']bipyridinyl-4-one 
• 78526-32-6 2,6-Dimethyl-4'-p-tolylsulfanyl-4'H-[1,1']bipyridinyl-4-one 
• 71831-58-8 2,6-Dimethyl-4'-(2-oxo-2-phenyl-ethyl)-4'H-[1,1']bipyridinyl-4-one 
• 71831-55-5 2,6-Dimethyl-4'-(2-oxo-cyclohexyl)-4'H-[1,1']bipyridinyl-4-one 
• 76639-16-2 2,6-Dimethyl-4'-(2-oxo-cyclohex-3-enyl)-4'H-[1,1']bipyridinyl-4-one 

Downstream Products

• 108-48-5 2,6-dimethylpyridine 
• 3512-75-2 4-chloro-2,6-lutidine 
• 13603-45-7 2,6-dimethyl-4-hydroxy-3-nitropyridine 
• 86775-90-8 (2,6-dimethyl-pyridin-4-yl)-phenyl-amine 
• 138642-53-2 2,6-dimethyl-3-formyl-4(1H)-pyridone 
• 31872-55-6 2,6-dimethyl-3,5-dinitro-4-pyridinol 
• 116387-98-5 2-(2,6-Dimethyl-pyridin-4-yloxy)-1-phenyl-ethanone 
• 122957-45-3 2,6-dimethyl-3-nitro-4(1H)-pyridone 
• 15513-48-1 4-chloro-2,6-dimethyl-3-nitropyridine 
• 138677-38-0 2,6-Dimethyl-4-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethoxy]-pyridine-3-carbaldehyde 
• 111079-38-0 4,6-dimethyl-2-phenylthieno<3,2-c>pyridine 
• 111079-37-9 4-chloro-2,6-dimethyl-3-phenylethynylpyridine 
• 88545-07-7 3-chloro-2,6-dimethyl-4(1H)-pyridinone 
• 909848-16-4 5-chloro-2,6-dimethyl-6'-({4-[(trifluoromethyl)oxy]phenyl}oxy)-3,3'-bipyridin-4(1H)-one 

Relevant articles and documents

Synthetic Applications of N-N Linked Heterocycles. Part 12. The Preparation of 4-Alkylthio- and 4-Arylthio-pyridines by Regiospecific Attack of Thioalkoxide Ions on N-(4-Oxopyridin-1-yl)pyridinium Salts

Thiolate ions add regiospecifically to N-(4-oxopyridin-1-yl)pyridinium salts (2)-(7) to give in good to excellent yields only the 1,4-dihydropyridine adducts (8)-(13), regardless of whether or not the pyridone moiety carries substituents for sterically shielding the 2- and 6-positions of the pyridinium ring.The addition is believed to be thermodynamically controlled.Decomposition of the dihydro-adducts under free-radical conditions, or by pyrolysis, gives good yields of pyridin-4-yl thioethers (14) and (16) though the reaction failed with the 2-methyl adducts (9).An improved synthesis of 6-methyl-4-oxopyran-2-carboxylic acid is also described.

Synthetic Applications of N-N Linked Heterocycles. Part 14. The Preparation of α-(4-Pyridyl)esters and α-(4-Pyridyl)nitriles by Regiospecific Attack of Ester and Nitrile Anions on Pyridinium Salts

Reactions between N-(2,6-dimethyl-4-oxopyridin-1-yl)pyridinium tetrafluoroborate (1) and lithio-derivatives of esters and nitriles give only low yields of 1,4-dihydro-adducts (3) and (7) due apparently to competing proton abstraction from the pyridone methyl groups.This limitation with salt (1) appears only with C-H acids of pKa > 20.Decomposition of the adducts under free-radical conditions yields α-(4-pyridyl)-esters (4) and -nitriles (8) essentially quantitatively.The same pyridyl-esters and -nitriles may be prepared conveniently in good overall yields by the reaction between the appropriate lithium salts and N-triphenylmethylpyridinium salts.The scope and limitations of the method are discucced. 2-Methyl-N-triphenylmethylpyridinium tetrafluoroborate is reported for the first time.

Synthetic Applications of N-N Linked Heterocycles. Part 7. The Preparation of 4-Alkyl- and 4-Aryl-pyridines by Regiospecific Attack of Grignard Reagents γ to Quaternary Nitrogen in N-(2,6-Dimethyl-4-oxopyridin-1-yl)pyridinium Salts

N-(2,6-Dimethyl-4-oxopyridin-1-yl)pyridinium salts (4), new reagents for the regiospecific synthesis of 4-substituted pyridines, give moderate to high yields of 4-alkyl- and 4-aryl-pyridines (8) - (10) on reaction with Grignard reagents.The scope and limitations on the reaction, which proceeds via 1,4-dihydro-intermediates (5) - (7), are explored.No 2-substituted pyridines were detected.Some reactions with organolithium compounds are also described.