93271-59-1

Basic information

• Product Name: 2-Hydroxy-4-methylpyridine-3-carbonitrile
• Synonyms: 2-Hydroxy-4-methylpyridine-3-carbonitrile;3-Cyano-4-methyl-2-pyridone;4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile;2-hydroxy-4-Methylnicotinonitrile;1,2-dihydro-4-Methyl-2-oxo-3-Pyridinecarbonitrile;1,2-dihydro-4-Methyl-2-oxopyridine-3-carbonitrile;3-Cyano-2-hydroxy-4-methylpyridine;3-Pyridinecarbonitrile,1,2-dihydro-4-Methyl-2-oxo-
• CAS NO: 93271-59-1
• Molecular Formula: C₇H₆N₂O
• Molecular Weight: 134.13
• Product Categories: Pyridine
• Mol File: 93271-59-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 234.7-236.1 °C
• Boiling Point: 337.65ºC at 760 mmHg
• Flash Point: 158.005ºC
• Appearance: /
• Density: 1.209g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.553
• PKA: 8.96±0.10(Predicted)
• CAS DataBase Reference: 2-Hydroxy-4-methylpyridine-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hydroxy-4-methylpyridine-3-carbonitrile(93271-59-1)
• EPA Substance Registry System: 2-Hydroxy-4-methylpyridine-3-carbonitrile(93271-59-1)

Safety Data

• Hazardous Substances Data: 93271-59-1(Hazardous Substances Data)

Usage

General Description

2-Hydroxy-4-methylpyridine-3-carbonitrile is a chemical compound with the molecular formula C7H6N2O. It is an important intermediate used in the synthesis of pharmaceuticals and agrochemicals. 2-Hydroxy-4-methylpyridine-3-carbonitrile has a pyridine ring with a hydroxyl group and a methyl group attached to it, as well as a cyano group attached to the third carbon atom. It is commonly used in the production of various drugs and pesticides due to its versatile reactivity and functional groups, making it a valuable building block for the pharmaceutical and agricultural industries. Additionally, it is also used as a precursor in the manufacturing of organic and inorganic compounds, and can also be employed as a chelating agent and metal complexation reagent in chemical research and industrial processes.

InChI:InChI=1/C7H6N2O/c1-5-2-3-9-7(10)6(5)4-8/h2-3H,1H3,(H,9,10)

Upstream product

• 65996-11-4 1-carbethoxy-1-cyano-2-methyl-4-dimethylamino-1,4-butadiene 
• 71493-76-0 2-amino-4-methylpyridine-3-carbonitrile 
• 41125-09-1 3-oxo-butyraldehyde; sodium enolate 
• 107-91-5 cyanoacetic acid amide 
• 5436-21-5 acetylacetaldehyde dimethyl acetal 
• 109-77-3 malononitrile 
• 1025080-30-1 [(2E)-3-methoxy-1-methylprop-2-en-1-ylidene]malononitrile 
• 410547-37-4 4,4-dicyano-3-methyl-3-butenal dimethyl acetal 
• 410547-38-5 1,1-dicyano-4-methoxy-2-methyl-1,3-butadiene 
• 759-58-0 ethyl isopropylidenecyanoacetate 
• 93271-58-0 2-isopropylidenecyanoacetamide 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 

Downstream Products

• 65169-38-2 2-chloro-4-methyl-3-pyridinecarbonitrile 
• 57839-80-2 3-Acetyl-4-methyl-2(1H)-pyridon 
• 133627-45-9 3-Amino-2-chloro-4-methylpyridine 
• 1698293-93-4 4-methyl-2-(1-methylethyl)-3-pyridinamine 

Relevant articles and documents

Antitumor compound used as AXL inhibitor and application of antitumor compound

The invention discloses a compound shown in a general formula (I) or pharmaceutically acceptable salt of the compound and preparation methods of the compound and the salt, and further discloses pharmaceutical composition containing the compound and an application of the compound and the pharmaceutical composition in preparation of an AXL inhibitory drug. The AXL inhibitory drug is used for treating tumor, nephropathy, immune system disease or circulatory system disease.

Polypharmacological profile of 1,2-dihydro-2-oxo-pyridine-3-carboxamides in the endocannabinoid system

The endocannabinoid system (ECS) represents one of the major neuromodulatory systems involved in different physiological and pathological processes. Multi-target compounds exert their activities by acting via multiple mechanisms of action and represent a promising pharmacological modulation of the ECS. In this work we report 4-substituted and 4,5-disubstituted 1,2-dihydro-2-oxo-pyridine-3-carboxamide derivatives with a broad spectrum of affinity and functional activity towards both cannabinoid receptors and additional effects on the main components of the ECS. In particular compound B3 showed high affinity for CB1R (Ki = 23.1 nM, partial agonist) and CB2R (Ki = 6.9 nM, inverse agonist) and also significant inhibitory activity (IC50 = 70 nM) on FAAH with moderate inhibition of ABHD12 (IC50 = 2.5 μΜ). Compounds B4, B5 and B6 that act as full agonists at CB1R and as partial agonists (B5 and B6) or antagonist (B4) at CB2R, exhibited an additional multi-target property by inhibiting anandamide uptake with sub-micromolar IC50 values (0.28–0.62 μΜ). The best derivatives showed cytotoxic activity on U937 lymphoblastoid cells. Finally, molecular docking analysis carried out on the three-dimensional structures of CB1R and CB2R and of FAAH allowed to rationalize the structure-activity relationships of this series of compounds.

A concise synthesis of 2-chloro-3-amino-4-methylpyridine

An improved and commercially valuable process is developed for the scalable synthesis of 2-chloro-3-amino-4-methylpyridine (CAPIC), a key intermediate of Nevirapine. The synthesis was accomplished in four steps, featuring condensation starting from 4,4-dimethoxyl-2-butanone and cyanoacetamide with ammonium acetate and acetic acid as catalysts. The total yield of the process is 62.1%. The pure CAPIC sample was confirmed with FTIR, 1H NMR, and 13C NMR spectra.