3749-51-7

Basic information

• Product Name: 2,4-DIHYDROXY-6-METHYLPYRIDINE
• Synonyms: 2,4-Dihydroxy-6-Methylpyridine, 97% 5GR;2,4-Dihydroxy-6-methylpyridine, 4,6-Dihydroxy-2-picoline;2,4-DIHYDROXY-6-METHYLPYRIDINE;4-HYDROXY-6-METHYL-2-PYRIDINONE;6-Methylpyridine-2,4-diol;4-Hydroxy-6-methyl-2(1H)-pyridone;4-Hydroxy-6-methylpyridin-2(1H)-one;2,4-Dihydroxy-6-methylpyridine,97%
• CAS NO: 3749-51-7
• Molecular Formula: C₆H₇NO₂
• Molecular Weight: 125.13
• Product Categories: Pyridines
• Mol File: 3749-51-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 324-327
• Boiling Point: 255.8 °C at 760 mmHg
• Flash Point: 108.5 °C
• Appearance: Beige/Powder
• Density: 1.269
• Vapor Pressure: 0.00241mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 2,4-DIHYDROXY-6-METHYLPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIHYDROXY-6-METHYLPYRIDINE(3749-51-7)
• EPA Substance Registry System: 2,4-DIHYDROXY-6-METHYLPYRIDINE(3749-51-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• Hazardous Substances Data: 3749-51-7(Hazardous Substances Data)

Usage

Description

2,4-Dihydroxy-6-methylpyridine is an organic compound characterized by its beige powder form. It is a significant synthetic intermediate in the chemical industry, known for its role in the preparation of various pharmaceutical compounds and substances with antimicrobial properties.

Uses

Used in Pharmaceutical Industry:
2,4-Dihydroxy-6-methylpyridine is used as a synthetic intermediate for the development of p38 kinase inhibitors. These inhibitors play a crucial role in managing and treating a range of inflammatory diseases and conditions by targeting the p38 kinase enzyme, which is involved in the regulation of cellular responses to stress and inflammation.
Additionally, 2,4-Dihydroxy-6-methylpyridine is utilized in the synthesis of Favipucine analogs. Favipucine is an antimicrobial and fungicidal agent, and its analogs are developed to enhance the effectiveness against various microbial infections, including bacterial and fungal pathogens. This application is particularly relevant in the field of medicine and pharmaceuticals, where the continuous development of new antimicrobial agents is essential to combat drug-resistant infections.

InChI:InChI=1/C6H7NO2/c1-4-2-5(8)3-6(9)7-4/h2-3H,1H3,(H2,7,8,9)

Upstream product

• 856834-08-7 2,4-diethoxy-6-methyl-pyridine 
• 10350-10-4 ethyl 2,4-dihydroxy-6-methylnicotinate 
• 520-45-6 Dehydracetic acid 
• 42779-56-6 2,4-dichloro-6-methyl-pyridine 
• 3749-51-7 4-hydroxy-6-methyl-2-pyridone 
• 67-64-1 acetone 
• 100-46-9 benzylamine 
• 7647-01-0 hydrogenchloride 
• 541-98-0 6-methyl-pyran-2,4-dione 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 1332372-75-4 C₉H₁₃NO₃ 
• 130473-38-0 2,2-dimethyl-6-(2-oxo-2-methylethyl)-4H-1,3-dioxin-4-one 

Downstream Products

• 13959-08-5 4-acetoxy-6-methyl-pyridin-2-ol 
• 79055-52-0 2,4-dibromo-6-methylpyridine 
• 42779-56-6 2,4-dichloro-6-methyl-pyridine 
• 4966-90-9 2,4-Dihydroxy-6-methyl-3-nitropyridine 
• 58096-00-7 6-methyl-4-(N'-phenyl-hydrazino)-pyridin-2-ol 
• 59225-86-4 4,7-dimethyl-6H-pyrano[3,2-c]pyridine-2,5-dione 
• 59225-87-5 2,7-dimethyl-6H-pyrano[3,2-c]pyridine-4,5-dione 
• 40334-96-1 2,4-dimethoxy-6-methyl-pyridine 
• 40334-98-3 2-Methoxy-1,6-dimethyl-4-pyridone 
• 72982-87-7 4-Methoxy-6-methyl-2-pyridone 
• 74990-56-0 4-(3-Methoxy-phenylamino)-6-methyl-1H-pyridin-2-one 
• 74990-57-1 4-(3-chloro-anilino)-6-methyl-1H-pyridin-2-one 
• 61190-99-6 methyl-6 benzylamino-4 pyridone 
• 193887-94-4 2-amino-5,6-dihydro-7-methyl-5-oxo-4-phenyl-4H-pyrano[3,2-c]pyridine-3-carbonitrile 

Relevant articles and documents

Structural and electronic modifications of pyridones and pyrones via regioselective bromination and trifluoromethylation

We report regioselective functionalization of pyridones and pyrones via electrophilic bromination (Br2) or radical trifluoromethylation (NaSO2CF3/tBuOOH) at the 3-position. Counter-intuitively, the 3-position EW groups decreased the carbonyl stretching energy by 6–23 cm?1; however, 3,5-dibromination increased the C[dbnd]O frequency by 10–22 cm?1 compared to the 3-Br pyridones. X-ray crystallography revealed pyridone tautomers with contracted C[dbnd]O bond metrics. pKa values and 1H NMR shifts for the series 3-H→Br→CF3 revealed the expected trend of increasing acidity (pKa = 8.85 → 8.33→6.78, MeOH) and increasing chemical shifts (10.97 → 11.42→11.71 DMSO-d6). We conclude that the paradoxical decrease in CO stretching frequencies by the 3-positoin EW groups is explained by an ‘assistive’ electron-withdrawing effect, whereby the 3-position EW group assists the electronegative oxygen atom in recruiting more electron density, and – as a result – attaining more oxyanion character (decreased the C[dbnd]O bond strength).

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COUMARIN-LIKE CYCLIC COMPOUND AS MEK INHIBITOR AND USE THEREOF

Disclosed are a class of coumarin-like cyclic compounds as MEK inhibitors and pharmaceutical compositions comprising the compounds, and the use of same in the preparation of a drug for treating MEK-related diseases. Particularly disclosed are compounds as shown in formula (I) and pharmaceutically acceptable salts thereof or tautomers thereof.

Small molecule inhibitors of anthrax edema factor

Anthrax is a highly lethal disease caused by the Gram-(+) bacteria Bacillus anthracis. Edema toxin (ET) is a major contributor to the pathogenesis of disease in humans exposed to B. anthracis. ET is a bipartite toxin composed of two proteins secreted by the vegetative bacteria, edema factor (EF) and protective antigen (PA). Our work towards identifying a small molecule inhibitor of anthrax edema factor is the subject of this letter. First we demonstrate that the small molecule probe 5′-Fluorosulfonylbenzoyl 5′-adenosine (FSBA) reacts irreversibly with EF and blocks enzymatic activity. We then show that the adenosine portion of FSBA can be replaced to provide more drug-like molecules which are up to 1000-fold more potent against EF relative to FSBA, display low cross reactivity when tested against a panel of kinases, and are nanomolar inhibitors of EF in a cell-based assay of cAMP production.