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

Chemical Properties

CLEAR YELLOWISH TO BROWN-RED LIQUID AFTER MELTING

Uses

1-Methyl-2-pyridone is used as a reactant in the trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis.

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 
• 2044-27-1 1-methyl-2-pyridinethione 
• 67367-26-4 2-methoxynicotinic acid methyl ester 
• 74925-37-4 ethyl 2-methoxypyridine-5-carboxylate 
• 873968-81-1 2,2-dichloro-1-methyl-1,2-dihydro-pyridine 
• 7732-18-5 water 
• 1628-89-3 2-methoxypyridine 
• 882980-43-0 2-benzyloxy-1-methylpyridinium triflate 
• 57-88-5 cholesterol 
• 72657-23-9 methyl (R)-3-hydroxy-2-methylpropionate 

Downstream Products

• 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 
• 14529-54-5 3,5-dibromo-1-methyl-1H-pyridin-2-one 
• 32896-90-5 1-methyl-5-nitro-2(1H)-pyridone 
• 14150-94-8 3,5-dinitro-1-methyl-2-pyridone 
• 109-09-1 2-chloropyridine 
• 13070-07-0 1-methylpiperidine-2-thione 

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.

Iron-Catalyzed Reactions of 2-Pyridone Derivatives: 1,6-Addition and Formal Ring Opening/Cross Coupling

In the presence of simple iron salts, 2-pyridone derivatives react with Grignard reagents under mild conditions to give the corresponding 1,6-addition products; if the reaction medium is supplemented with an aprotic dipolar cosolvent after the actual addition step, the intermediates primarily formed succumb to ring opening, giving rise to non-thermodynamic Z,E-configured dienoic acid amide derivatives which are difficult to make otherwise. Control experiments as well as the isolation and crystallographic characterization of a (tricarbonyl)iron pyridone complex suggest that the active iron catalyst generated in situ exhibits high affinity to the polarized diene system embedded into the heterocyclic ring system of the substrates, which likely serves as the actual recognition element.