2-Hydroxy-5-methylpyridine Chemical Properties

Melting point:

183-187 °C (lit.)

Boiling point:

304.2±15.0 °C(Predicted)

Density 

1.053±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)

form 

Solid

pka

12.43±0.10(Predicted)

color 

Pale Yellow to Light Yellow

BRN 

107074

InChI

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

InChIKey

SOHMZGMHXUQHGE-UHFFFAOYSA-N

SMILES

C1(=O)NC=C(C)C=C1

CAS DataBase Reference

1003-68-5(CAS DataBase Reference)

NIST Chemistry Reference

2(1H)-pyridinone, 5-methyl-(1003-68-5)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41-36/37/39

Safety Statements 

26-36-37

WGK Germany 

3

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Hydroxy-5-methylpyridine Usage And Synthesis

Chemical Properties

White Solid

Uses

2-Hydroxy-5-methylpyridine (cas# 1003-68-5) is a useful compound for organic synthesis. In particular it has been used for the diastereoselective preparation of cyclobutane-fused pyridinyl sulfonyl fluorides. 2-hydroxy-5-methylpyridine and Iodobenzene were the impurities present in Pirfenidone (PFD) drug substance. PFD is a novel antifibrotic agent approved for mild to moderate Idiopathic pulmonary fibrosis (IPF) as orphan drug[1].

Definition

ChEBI: 5-Methyl-2-pyridinol is a member of methylpyridines.

Synthesis

3-cyano-6-hydroxypyridine and sodium lauryl sulfate were added to a mixed solvent of n-butanol and water. Subsequently, the temperature was raised to 50 °C., and sulfuric acid water obtained by dissolving 98% sulfuric acid in water was added dropwise at the temperature. After stirring for about 20 minutes, the mixture was cooled to room temperature, and 5% Pd / C was added. The system was replaced with hydrogen, and hydrogenation was carried out at atmospheric pressure for 6 hours. After the reaction was completed, the catalyst was removed by filtration, and the solution was washed with 10% sodium hydroxide aqueous solution. After partially neutralizing to H = 5 and extraction with n-butanol, a solution of crude 3-methyl-6-hydroxypyridine in butanol was obtained. When this solution was quantified by liquid chromatography, the pass-through rate was 99.2%, and the yield of 2-hydroxy-5-methylpyridine was 83%.

References

[1] Suresh Babu Bodempudi, ;K. S. Reddy, Ravichandra Babur. “Development and Substantiation of a RP-HPLC Method for Monitoring of Impurities in Pirfenidone Drug Substance.” 美国分析化学(英文) 6 1 (2015): 1019–1029.

2-Hydroxy-5-methylpyridine(1003-68-5)Related Product Information

• 2-Hydroxypyridine
• Kresoxim-methyl
• 2-Hydroxy-5-nitropyridine
• Methyl acetate
• 2,6-Lutidine
• METSULFURON METHYL
• Tribenuron methyl
• Azamethiphos
• CHLOROPHOSPHONAZO III
• Methyl propyl carbonate
• Pirimiphos-methyl
• 4-Methylpyridine
• 3-Hydroxypyridine
• 2-Chloro-5-chloromethylpyridine
• Methyl salicylate
• Thiophanate-methyl
• 2,4,6-Collidine
• 3-Amino-6-hydroxypyridine