27805-12-5

Basic information

• Product Name: 3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester
• Synonyms: 3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester;ethyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile;ETHYL 2-HYDROXYPYRIDINE-3-CARBOXYLATE;2-Oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester;2-Oxo-1,2-dihydro-pyridine-3-carboxylic acid tert-butyl ester;Ethyl 2-oxo-1,2-dihydropyridine-3-carboxylate
• CAS NO: 27805-12-5
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16
• Mol File: 27805-12-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 369.661°C at 760 mmHg
• Flash Point: 177.365°C
• Appearance: /
• Density: 1.214g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.512
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester(27805-12-5)
• EPA Substance Registry System: 3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester(27805-12-5)

Safety Data

• Hazardous Substances Data: 27805-12-5(Hazardous Substances Data)

Usage

Description

3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester, also known as Ethyl 2-oxo-1,2-dihydropyridine-3-carboxylate, is a chemical compound that belongs to the class of pyridinecarboxylic acids, specifically esters of such acids. It is a product of condensation between an acid and an alcohol, with a molecular formula of C9H9NO3. This ester is commonly used in organic synthesis and, like many esters, it likely has a fruity or sweet scent. As with all chemicals, appropriate safety and handling procedures must be followed due to potential hazards associated with its use.

Uses

Used in Organic Synthesis:
3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester is used as a key intermediate in the synthesis of various organic compounds. Its versatile chemical structure allows it to be a valuable building block in the preparation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester is used as a starting material for the development of new drugs. Its unique structure can be modified to create potential therapeutic agents with novel properties, such as improved efficacy, selectivity, or reduced side effects.
Used in Agrochemical Industry:
3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester is also used in the agrochemical industry as a precursor for the synthesis of new pesticides or herbicides. Its chemical properties can be tailored to target specific pests or weeds, leading to more effective and environmentally friendly agricultural products.
Used in Flavor and Fragrance Industry:
Due to its likely fruity or sweet scent, 3-Pyridinecarboxylic acid, 1,2-dihydro-2-oxo-, ethyl ester can be used as a component in the flavor and fragrance industry. It can contribute to the creation of new and complex scents for perfumes, cosmetics, or food products, enhancing the sensory experience for consumers.

InChI:InChI=1/C8H9NO3/c1-2-12-8(11)6-4-3-5-9-7(6)10/h3-5H,2H2,1H3,(H,9,10)

Upstream product

• 64-17-5 ethanol 
• 609-71-2 1,2-dihydro-2-oxonicotinic acid 
• 17758-13-3 1-phenyl-2(1H)-pyrimidinone 
• 105-53-3 diethyl malonate 
• 17758-14-4 1-p-tolylpyrimidin-2(1H)-one 
• 20577-27-9 2-hydroxy-3-cyanopyridine 
• 110-89-4 piperidine 
• 609-71-2 2-hydroxy-3-carboxypyridine 
• 28369-76-8 2-hydroxynicotinic acid chloride 

Downstream Products

• 10128-92-4 1,2-dihydro-2-oxopyridine-3-carboxamide 
• 153336-74-4 2-hydroxynicotinohydrazide 
• 16498-79-6 ethyl 2-methoxynicotinate 
• 15506-19-1 1-Methyl-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester 

Relevant articles and documents

ISOINDOLINONE DERIVATIVES AS IRAK4 MODULATORS

Compounds of Formula (0), and stereoisomers and pharmaceutically acceptable salts thereof, as well as methods of use as Interleukin-1 Receptor Associated Kinase (IRAK4) inhibitors are described herein.

Potent antimicrobial agents against azole-resistant fungi based on pyridinohydrazide and hydrazomethylpyridine structural motifs

Abstract Schiff base derivatives have recently been shown to possess antimicrobial activity, and these derivatives include a limited number of salicylaldehyde hydrazones. To further explore this structure-activity relationship between salicylaldehyde hydrazones and antifungal activity, we previously synthesized and analyzed a large series of salicylaldehyde and formylpyridinetrione hydrazones for their ability to inhibit fungal growth of both azole-susceptible and azole-resistant species of Candida. While many of these analogs showed excellent growth inhibition with low mammalian cell toxicity, their activity did not extend to azole-resistant species of Candida. To further dissect the structural features necessary to inhibit azole-resistant fungal species, we synthesized a new class of modified salicylaldehyde derivatives and subsequently identified a series of modified pyridine-based hydrazones that had potent fungicidal antifungal activity against multiple Candida spp. Here we would like to present our synthetic procedures as well as the results from fungal growth inhibition assays, mammalian cell toxicity assays, time-kill assays and synergy studies of these novel pyridine-based hydrazones on both azole-susceptible and azole-resistant fungal species.

Role of lactam vs. lactim tautomers in 2(1H)-pyridone catalysis of aromatic nucleophilic substitution

3-Ethylaminocarbonyl-2(1H)-pyridone 1 and 3-ethoxycarbonyl-2(1H)-pyridone 2 have been synthesised and tested as catalysts for the aromatic nucleophilic substitution of fluoride by piperidine in 2-fluoro-5-nitrobenzonitrile 3. A kinetic model which takes into account the dimerisation of the catalysts has been developed, which allows a quantitative analysis of measured data. 3-Ethylaminocarbonyl-2(1H)-pyridone 1 exists exclusively as a lactam tautomer, either monomeric or dimeric but 3-ethoxycarbonyl-2(1H)-pyridone 2 exists as a lactim monomer, whereas its dimer exists in the lactam form. Despite such differences, these two compounds exhibit similar catalytic efficiencies for the reaction studied, suggesting that lactim and lactam tautomers have comparable efficiencies in tautomeric catalysis.