694-85-9

Basic information

• Product Name: 1-Methyl-2-pyridone
• Synonyms: 1-Methyl-1,2-dihydro-2-pyridinone;1-Methyl-1H-pyridin-2-one;1-methyl-2(1h)-pyridinon;1-Methyl-2(1H)-pyridinone;1-methyl-2(1h)-pyridon;1-Methyl-2(1H)-pyridone;1-Methyl-2-oxopyridine;1-Methyl-2-pyridinone
• CAS NO: 694-85-9
• Molecular Formula: C₆H₇NO
• Molecular Weight: 109.13
• EINECS: 211-777-2
• Product Categories: Heterocyclic Compounds;C6;Heterocyclic Building Blocks;Pyridines
• Mol File: 694-85-9.mol
• Article Data: 50

Chemical Properties

• Melting Point: 30-32 °C(lit.)
• Boiling Point: 250 °C740 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear brown solid.
• Density: 1.129 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0222mmHg at 25°C
• Refractive Index: n20/D 1.569
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 0.30±0.62(Predicted)
• Water Solubility: Soluble in water (1000 mg/ml at 20°C).
• BRN: 107805
• CAS DataBase Reference: 1-Methyl-2-pyridone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-2-pyridone(694-85-9)
• EPA Substance Registry System: 1-Methyl-2-pyridone(694-85-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: UV1148100
• F: 10-21
• TSCA: Yes
• Hazardous Substances Data: 694-85-9(Hazardous Substances Data)

Usage

Description

1-Methyl-2-pyridone, also known as 2-acetylpyridine, is an organic compound with the chemical formula C6H6NO. It is a heterocyclic compound that features a pyridine ring with a methyl group at the 1-position and a carbonyl group at the 2-position. 1-Methyl-2-pyridone is known for its versatile reactivity and is commonly used in various chemical synthesis processes.

Uses

Used in Pharmaceutical Industry:
1-Methyl-2-pyridone is used as a reactant in the trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis. This process is particularly important in the synthesis of pharmaceutical compounds, as trifluoromethylated molecules often exhibit enhanced biological activity and metabolic stability.
Used in Chemical Synthesis:
1-Methyl-2-pyridone is used as a versatile building block in the synthesis of various organic compounds. Its reactivity allows it to participate in a wide range of chemical reactions, making it a valuable intermediate in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Chemical Properties:
1-Methyl-2-pyridone is a clear yellowish to brown-red liquid after melting. Its physical properties, such as solubility and boiling point, make it suitable for use in various chemical processes and reactions.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 416, 1956 DOI: 10.1021/ja01583a045The Journal of Organic Chemistry, 45, p. 4508, 1980 DOI: 10.1021/jo01310a052Tetrahedron Letters, 25, p. 1591, 1984 DOI: 10.1016/S0040-4039(01)90019-X

InChI:InChI=1/C6H7NO/c1-7-5-3-2-4-6(7)8/h2-5H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 142-08-5 2-Pyridone 
• 110-86-1 pyridine 
• 80-48-8 methyl p-toluene sulfonate 
• 74-88-4 methyl iodide 
• 41681-14-5 1-Methyl-2-(methylthio)pyridinium iodide 
• 3902-84-9 potassium 2-oxo-2H-pyridin-1-ide 
• 77-78-1 dimethyl sulfate 
• 4088-63-5 1-methyl-2(1H)-pyridinimine 
• 2044-27-1 1-methyl-2-pyridinethione 
• 3847-19-6 2-acetoxypyridine 
• 121-69-7 N,N-dimethyl-aniline 
• 110-94-1 1,5-pentanedioic acid 
• 67367-26-4 2-methoxynicotinic acid methyl ester 

Downstream Products

• 109-09-1 2-chloropyridine 
• 51859-09-7 1-methyl-2-pyridone phenylimine 
• 51859-08-6 2-benzylidene-1-methyl-1,2-dihydro-pyridine 
• 16110-09-1 2,5 dichloropyridine 
• 931-20-4 1-methylpiperidin-2-one 
• 13131-19-6 (1R,8S)-9-Methyl-9-aza-tricyclo[6.2.2.0^2,7]dodeca-2,4,6,11-tetraen-10-one 
• 13131-19-6 (1S,8R)-9-Methyl-9-aza-tricyclo[6.2.2.0^2,7]dodeca-2⁽⁷⁾,3,5,11-tetraen-10-one 
• 13131-19-6 2-methyl-5,6-benzo-2-azabicyclo<2.2.2>oct-7-ene-3-one 
• 86863-93-6 2-(Ethoxycarbonyl)-1-(trimethylsilyl)benzol 
• 121463-25-0 (1R,6R)-1,6-Bis-(2-chloro-phenyl)-1,6-diphenyl-hexa-2,4-diyne-1,6-diol; compound with 1-methyl-1H-pyridin-2-one 
• 91168-58-0 1,2-dihydro-2-(4-ethoxybenzoylcyanomethylidene)-1-methylpyridine 
• 121463-31-8 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1-methyl-1H-pyridin-2-one 
• 81971-39-3 5-bromo-1-methylpyridin-2(1H)-one 
• 81971-38-2 3-bromo-1-methyl-1H-pyridin-2-one 

Relevant articles and documents

Accelerated hydrolysis of α-halo and α-cyano pyridinium relative to uracil derivatives: A model for ODCase-catalyzed hydrolysis of 6-cyanoUMP

α-Halo and α-cyano pyridiniums were found to undergo facile hydrolysis, in contrast to the sluggish reactions of corresponding uracils. The greatly enhanced rates found with pyridinium compounds have indicated a possible source of the rate acceleration seen in the hydrolysis of 6-cyanouridine 5′-monophosphate catalyzed by orotidine 5′-monophosphate decarboxylase.

Micellar Effects upon the Reaction of Hydroxide Ion with N-Alkyl-2-bromopyridinium Ion

The reactivity of N-alkyl-2-bromopyridinium ions (alkyl = Me, Et, n-C12H25, n-C14H29, n-C16H33) toward OH(-) is affected by cationic micelles of alkyltrimethylammonium chloride or bromide (alkyl = n-C14H29, n-C16H33) which inhibit reactions of the methyl

Manganese-Promoted Regioselective Direct C3-Phosphinoylation of 2-Pyridones

A highly efficient and regioselective manganese-induced radical oxidative direct C?P bond formation between 2-pyridones and secondary phosphine oxides was developed. The C3-selective phosphinoylation was conveniently achieved through a combination of substoichiometric manganese and persulfate oxidant under mild conditions. Various 3-phosphinoylated pyridone products can be obtained in moderate to high yields. Preliminary mechanistic studies suggest that the reaction is likely to involve a radical pathway induced by catalytically active Mn3+ species.

Metal-free regioselective direct thiolation of 2-pyridones

A highly regioselective metal-free direct C-H thiolation of 2-pyridones with disulfides or thiols has been developed. A combination of persulfate and a commercially available halide source such as LiCl, NCS or I2 enables the successful direct incorporation of a sulfide moiety into the 5-position of pyridone under mild conditions, providing a useful and convenient approach for the preparation of a diverse array of 5-thio-substituted pyridones in moderate to excellent yields.