3279-76-3

Basic information

• Product Name: 2-Hydroxy-6-methylpyridine
• Synonyms: 6-Methyl-2(1H)-pyridone;6-Methyl-2-hydroxypyridine;6-Methyl-2-pyridyl alcohol;6-Methylpyridinone;6-METHYL-2-PYRIDINONE;6-METHYLPYRIDIN-2(1H)-ONE;AKOS BBS-00002969;TIMTEC-BB SBB004345
• CAS NO: 3279-76-3
• Molecular Formula: C₆H₇NO
• Molecular Weight: 109.13
• EINECS: 221-919-5
• Product Categories: Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;Pyridines
• Mol File: 3279-76-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 157-159 °C(lit.)
• Boiling Point: 131-133C
• Flash Point: 123.884 °C
• Appearance: White to cream/Crystalline Powder
• Density: 1.1143 (rough estimate)
• Vapor Pressure: 0.000724mmHg at 25°C
• Refractive Index: 1.5040 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.12±0.10(Predicted)
• BRN: 107073
• CAS DataBase Reference: 2-Hydroxy-6-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hydroxy-6-methylpyridine(3279-76-3)
• EPA Substance Registry System: 2-Hydroxy-6-methylpyridine(3279-76-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-40
• Safety Statements: 26-36-22
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 3279-76-3(Hazardous Substances Data)

Usage

Chemical Properties

white to cream-colored crystalline powder

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 1186, 1949 DOI: 10.1021/ja01172a014

General Description

2-Hydroxy-6-methylpyridine reacts with carboxylic acids RCOOH to give an equilibrium mixture of products M(2)(O(2)CR)(n)(mhp)(4-n) where R = 2-thienyl and phenyl. mhp is the anion formed from deprotonation of 2-hydroxy-6-methylpyridine.

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

Upstream product

• 66909-37-3 6-hydroxy-2-methyl-nicotinic acid 
• 109-04-6 2-bromo-pyridine 
• 3480-65-7 [1,2']bipyridinyl-2-one 
• 63071-03-4 2-methoxy-6-methyl-pyridine 
• 5315-25-3 2-bromo-6-methylpyridine 
• 103548-82-9 (4aR,5R,10bR)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-prop[1]eno-1,7-phenanthrolin-8(7H)-one 
• 89478-72-8 1-(4,6-Diphenyl-pyridine-2-carbonyl)-6-methyl-1H-pyridin-2-one 
• 92138-20-0 natural Huperzine A 
• 18617-77-1 6-methyl-2-ethoxypyridine 
• 407-22-7 2-fluoro-6-methylpyridine 
• 18613-73-5 2-hydroxy-6-methyl-pyridine-3,5-dicarboxylic acid diethyl ester 
• 4027-39-8 2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester 
• 31163-12-9 ethyl 6-chloro-2-methylnicotinate 
• 3424-43-9 ethyl 6-hydroxy-2-methylnicotinate 

Downstream Products

• 18368-63-3 6-chloro-2-picoline 
• 5315-25-3 2-bromo-6-methylpyridine 
• 3430-15-7 2,3,5-tribromo-6-methyl-pyridine 
• 22109-55-3 3,5-Dichlor-6-methyl-pyridin-2-ol 
• 39745-39-6 6-methyl-3-nitrohydropyridin-2-one 
• 63071-03-4 2-methoxy-6-methyl-pyridine 
• 16097-09-9 6-Phenethyl-1H-pyridin-2-one 
• 28369-92-8 2-methyl-6-phenoxypyridine 
• 859296-04-1 3-(6-methyl-2-oxo-2H-[1]pyridyl)-propionic acid 
• 122474-21-9 RuH(CO)(C₅H₃NOCH₃)(P(C₆H₅)3)2 
• 122474-22-0 RuCl(CO)(C₅H₃CH₃NO)(P(C₆H₅)3)2 
• 39112-84-0 5-hydroxy-6-methyl-2-pyridone 
• 777940-46-2 3-iodo-6-methyl-1H-2-pyridone 

Relevant articles and documents

Rhodium(III)-Catalyzed Site-Selective C-H Alkylation and Arylation of Pyridones Using Organoboron Reagents

In this study we developed a method for the pyridine-directed, rhodium-catalyzed, site-selective C-H alkylation and arylation of pyridones using commercially available trifluoroborate reagents. This simple and versatile transformation proceeded smoothly under relatively mild conditions with perfect site selectivity. The coupling groups in the boron reagents can be extended to primary alkyl, benzyl, and cycloalkyl. Moreover, direct C-H arylation products could also be obtained under similar conditions.

Rh(I)-Catalyzed C6-Selective Decarbonylative Alkylation of 2-Pyridones with Alkyl Carboxylic Acids and Anhydrides

A Rh-catalyzed chelation-assisted C6-selective C-H activation/alkylation of 2-pyridones with readily available alkyl carboxylic acids or anhydrides is introduced. The reaction proceeds via substrate decarbonylation. This approach merges C-H functionalization with readily available anhydrides, allowing for the efficient synthesis of various C6-alkylated 2-pyridones with good functional group tolerance.

Synthesis of 4-, 5-, and 6-methyl-2,2'-bipyridine by a negishi cross-coupling strategy: 5-Methyl-2,2'-bipyridine: [2,2'-bipyridine, 5-methyl-]

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