75358-89-3

Basic information

• Product Name: methyl 2-cyanopyridine-3-carboxylate
• Synonyms: Methyl 2-cyano-3-pyridinecarboxylate
• CAS NO: 75358-89-3
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.1454
• Mol File: 75358-89-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 318 °C at 760 mmHg
• Flash Point: 146.1 °C
• Appearance: /
• Density: 1.25 g/cm³
• Vapor Pressure: 0.000373mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: methyl 2-cyanopyridine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-cyanopyridine-3-carboxylate(75358-89-3)
• EPA Substance Registry System: methyl 2-cyanopyridine-3-carboxylate(75358-89-3)

Safety Data

• Hazardous Substances Data: 75358-89-3(Hazardous Substances Data)

Usage

General Description

Methyl 2-cyanopyridine-3-carboxylate is an organic compound with the chemical formula C8H6N2O2. It is a derivative of pyridine and contains a cyanide group and an ester group. It is a colorless to pale yellow liquid with a molecular weight of 162.14 g/mol. methyl 2-cyanopyridine-3-carboxylate has potential applications in the pharmaceutical industry for the development of new drugs and as a building block in organic synthesis. It is important to handle this chemical with care as it can be toxic and harmful if ingested, inhaled, or in contact with the skin.

InChI:InChI=1/C8H6N2O2/c1-12-8(11)6-3-2-4-10-7(6)5-9/h2-4H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 73112-09-1 2-cyanopyridine-3-carboxylic acid 
• 67-56-1 methanol 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 7677-24-9 trimethylsilyl cyanide 
• 5860-70-8 2-Aminocarbonylnicotinic acid 
• 79-22-1 methyl chloroformate 
• 699-98-9 Pyridine-2,3-dicarboxylic anhydride 
• 151-50-8 potassium cyanide 
• 91074-38-3 3-carbomethoxy-1-dimethylaminocarbonyloxypyridinium chloride 
• 15905-18-7 1-oxy-nicotinic acid methyl ester 
• 124-63-0 methanesulfonyl chloride 
• 55155-23-2 2,3-pyridinedicarboxylic acid chloride 

Downstream Products

• 151509-03-4 imidazo<1,5-a>pyridine-8-carbaldehyde 
• 151509-02-3 methyl imidazo<1,5-a>pyridine-8-carboxylate 
• 93617-20-0 1-[5-Oxo-5,6-dihydro-pyrrolo[3,4-b]pyridin-(7Z)-ylidene]-3-phenyl-urea 
• 93616-75-2 5-Amino-7-benzyl-7H-pyrido[2,3-d]pyridazin-8-one 
• 81214-63-3 8-aminopyrido<2,3-d>pyridazine-5(6H)-one 
• 73112-09-1 2-cyanopyridine-3-carboxylic acid 
• 93616-73-0 6-Benzylamino-7-imino-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one 
• 93616-70-7 7-(Benzyl-hydrazono)-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one 

Relevant articles and documents

Cyclic acyl amidines as unexpected C4-donors for fully substituted pyridine ring formation in the base mediated reaction with malononitrile

A new one-step, pseudo four-component approach for the synthesis of fully substituted pyridines via ring-opening of the cyclic acyl amidine of 3-amino-1H-isoindol-1-one and its aza-analogues during the reaction with malononitrile in the presence of sodium methoxide, followed by pyridine ring closure is reported. This method allows the one-step preparation of previously unknown 2-(pyridin-4-yl)(hetero)aryl carboxamides in good yields under mild reaction conditions.

Efficient Synthesis of Nicotinic Acid Based Pseudopeptides Bearing an Amidoxime Function

The synthesis of nicotinic acid based amino acid units bearing an amidoxime function on the pyridine ring has been developed. The starting 2-cyanonicotinic acid was efficiently coupled with methyl esters of l-α-amino acids to afford intermediate 2-cyanopyridin-3-yl-containing pseudopeptides together with the tautomeric methyl esters of (2S)-2-(7-imino-5-oxo-5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl)alkanoic acids. Regioselective pyrrolidine ring opening of these esters occurred upon hydroxylamine hydrochloride treatment, giving rise to the open-chain pyridin-3-yl 2-amidoxime pseudopeptides bearing the same structure as amidoximes obtained by direct hydroxyamination of the corresponding cyano esters.

1-ACYLOXYPYRIDINIUM ION: THE REACTIVE INTERMEDIATE IN A MODIFIED REISSERT-HENZE REACTION

Cyanation of 3-X-1-dimethylaminocarbonyloxypyridinium ions with trimethylsilanecarbonitrile or cyanide ion gives 3-methyl-2-pyridinecarbonitrile (ca.90percent) contaminated with 5-methyl-2-pyridinecarbonitrile (ca.10percent) when X = -CH3, and approximately equal amounts of the 3- and 5-X derivatives when X = -COOCH3.These product mixtures are identical to those obtained with the corresponding pyridine 1-oxides and dimethylcarbamoyl chloride in a modified Reissert-Henze reaction.