56394-28-6

Basic information

• Product Name: 3-CYANO-4,6-DIMETHYLCOUMARIN
• Synonyms: 3-CYANO-4,6-DIMETHYLCOUMARIN
• CAS NO: 56394-28-6
• Molecular Formula: C₁₂H₉NO₂
• Molecular Weight: 199.21
• Product Categories: Coumarins;Coumarin;API intermediates;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 56394-28-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 202-207 °C(lit.)
• Boiling Point: 364 °C at 760 mmHg
• Flash Point: 174.7 °C
• Appearance: /
• Density: 1.25 g/cm³
• Vapor Pressure: 1.74E-05mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: 3-CYANO-4,6-DIMETHYLCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CYANO-4,6-DIMETHYLCOUMARIN(56394-28-6)
• EPA Substance Registry System: 3-CYANO-4,6-DIMETHYLCOUMARIN(56394-28-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 56394-28-6(Hazardous Substances Data)

Usage

General Description

3-Cyano-4,6-dimethylcoumarin is a chemical compound with the molecular formula C12H9NO2. It is a coumarin derivative which is commonly used as a fluorogenic reagent for the detection of amino acids and peptides in biological samples. The compound is known for its fluorescent properties, making it useful in various biochemical assays and fluorescence microscopy. It also has potential applications in the development of new fluorogenic probes for biological imaging and sensing. Additionally, 3-cyano-4,6-dimethylcoumarin has been studied for its potential pharmaceutical properties, including anti-inflammatory and anti-cancer activities. Overall, this compound is valued for its unique properties and versatile applications in scientific research and development.

InChI:InChI=1/C12H9NO2/c1-7-3-4-11-9(5-7)8(2)10(6-13)12(14)15-11/h3-5H,1-2H3

Upstream product

• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 105-56-6 ethyl 2-cyanoacetate 
• 109-77-3 malononitrile 

Downstream Products

• 56394-29-7 4,6-Dimethyl-3-(tetrazol-5-yl)-cumarin 

Relevant articles and documents

One-Pot Green Synthesis of 2-Oxo-2H-chromene-3-carbonitriles Using Dual-Frequency Ultrasonication

Abstract: A green synthesis of 2-oxo-2H-chromene-3-carbonitriles has been carried out in one step by reacting 2-hydroxybenzaldehydes or 2-hydroxyacetophenones with ethyl cyanoacetate under dual-frequency ultrasonica-tion (ultrasonic bath of 40 KHz and probe of 20 KHz). The compounds were obtained in very high yield, and their structures were confirmed by IR and NMR data.

Iridium-catalyzed direct asymmetric vinylogous allylic alkylation

The catalytic asymmetric vinylogous allylic alkylation of α,β-unsaturated lactones (including coumarins) was achieved with excellent regio- and enantioselectivity. Transformations of the product were carried out by means of the versatile terminal olefin and lactone moieties. The synthetic application of the present methodology was showcased by the asymmetric synthesis of an advanced synthetic Merck intermediate toward a new drug candidate.

SYNTHESIS AND REACTIONS OF SOME 3-CYANO-4-METHYLCOUMARINS

o-Hydroxy ketones (I) were converted into 3-cyano-4-methylcoumarins (II) via condensation with ethyl cyanoacetate in presence of piperidine or ammonium acetate as catalyst.The behavior of compound (II) towards Grignard and Michael reactions was investigat