74133-20-3

Basic information

• Product Name: 4-Methoxypyridine-3-carbonitrile
• Synonyms: 4-METHOXY-NICOTINONITRILE ;4-Methoxypyridine-3-carbonitrile;4-Methoxy-3-Pyridinecarbonitrile
• CAS NO: 74133-20-3
• Molecular Formula: C₇H₆N₂O
• Molecular Weight: 134.14
• Mol File: 74133-20-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 269.1oC at 760 mmHg
• Flash Point: 116.6oC
• Appearance: /
• Density: 1.16g/cm3
• Vapor Pressure: 0.00738mmHg at 25°C
• Refractive Index: 1.526
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 4-Methoxypyridine-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxypyridine-3-carbonitrile(74133-20-3)
• EPA Substance Registry System: 4-Methoxypyridine-3-carbonitrile(74133-20-3)

Safety Data

• Hazardous Substances Data: 74133-20-3(Hazardous Substances Data)

Usage

General Description

4-Methoxypyridine-3-carbonitrile is a chemical compound with the molecular formula C7H6N2O. It is a derivative of pyridine and contains a methoxy group and a cyano group attached to the third position of the pyridine ring. 4-Methoxypyridine-3-carbonitrile is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It can also be used as a building block in the production of heterocyclic compounds. 4-Methoxypyridine-3-carbonitrile is a yellowish to orange solid with a melting point of around 98-100°C, and it is sparingly soluble in water but soluble in organic solvents such as methanol and ethanol. It is important to handle this compound with care as it can be harmful if inhaled, swallowed, or absorbed through the skin, and it may cause irritation to the respiratory system, skin, and eyes.

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

Upstream product

• 98645-43-3 2-chloro-3-cyano-4-methoxypyridine 
• 98645-42-2 2-bromo-4-methoxypyridine-3-carbonitrile 
• 33631-09-3 4-methoxypyridin-3-amine 
• 143-33-9 sodium cyanide 
• 124-41-4 sodium methylate 
• 89284-61-7 4-chloro-nicotinonitrile 
• 82257-15-6 4-methoxynicotinaldehyde 
• 620-08-6 4-methoxypyridine 
• 95689-38-6 1,1-dicyano-4-(N,N-dimethylamino)-2-methoxy-1,3-butadiene 

Downstream Products

• 524-40-3 ricinin 
• 609-70-1 4-hydroxynicotinic acid 

Relevant articles and documents

Characterization of nicotinamidases: Steady state kinetic parameters, classwide inhibition by nicotinaldehydes, and catalytic mechanism

Nicotinamidases are metabolic enzymes that hydrolyze nicotinamide to nicotinic acid. These enzymes are widely distributed across biology, with examples found encoded in the genomes of Mycobacteria, Archaea, Eubacteria, Protozoa, yeast, and invertebrates, but there are none found in mammals. Although recent structural work has improved our understanding of these enzymes, their catalytic mechanism is still not well understood. Recent data show that nicotinamidases are required for the growth and virulence of several pathogenic microbes. The enzymes of Saccharomyces cerevisiae, Drosophila melanogaster, and Caenorhabditis elegans regulate life span in their respective organisms, consistent with proposed roles in the regulation of NAD+ metabolism and organismal aging. In this work, the steady state kinetic parameters of nicotinamidase enzymes from C. elegans, Sa. cerevisiae, Streptococcus pneumoniae (a pathogen responsible for human pneumonia), Borrelia burgdorferi (the pathogen that causes Lyme disease), and Plasmodium falciparum (responsible for most human malaria) are reported. Nicotinamidases are generally efficient catalysts with steady state kcat values typically exceeding 1 s -1. The Km values for nicotinamide are low and in the range of 2 -110 μM. Nicotinaldehyde was determined to be a potent competitive inhibitor of these enzymes, binding in the low micromolar to low nanomolar range for all nicotinamidases tested. A variety of nicotinaldehyde derivatives were synthesized and evaluated as inhibitors in kinetic assays. Inhibitions are consistent with reaction of the universally conserved catalytic Cys on each enzyme with the aldehyde carbonyl carbon to form a thiohemiacetal complex that is stabilized by a conserved oxyanion hole. The S. pneumoniae nicotinamidase can catalyze exchange of 18O into the carboxy oxygens of nicotinic acid with H218O. The collected data, along with kinetic analysis of several mutants, allowed us to propose a catalytic mechanism that explains nicotinamidase and nicotinic acid 18O exchange chemistry for the S. pneumoniae enzyme involving key catalytic residues, a catalytic transition metal ion, and the intermediacy of a thioester intermediate.

Syntheses with nitriles LXXI: Synthesis of 4-hydroxynicotinic acid from butadienedicarbonitriles

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