56394-22-0

Usage

Uses

Used in Pharmaceutical Industry:
6-Bromo-3-cyano-4-methylcoumarin is used as an intermediate compound for the development of various pharmaceutical products. Its unique structure and properties make it a valuable building block in the synthesis of new drugs with potential therapeutic applications.
Used in Dye Industry:
In the dye industry, 6-Bromo-3-cyano-4-methylcoumarin is utilized as a key component in the preparation of methine dyes. These dyes are known for their vibrant colors and are used in a wide range of applications, including textiles, plastics, and printing inks.
Used in Chemical Research:
6-Bromo-3-cyano-4-methylcoumarin serves as an essential compound in chemical research, particularly in the field of heterocyclic chemistry. Its unique structure allows researchers to explore new synthetic pathways and develop novel compounds with diverse applications.
Used in Bioactive Compounds Synthesis:
6-Bromo-3-cyano-4-methylcoumarin is also used as a starting material for the synthesis of bioactive compounds. These compounds have the potential to be developed into new drugs or used in various biological applications, such as targeting specific enzymes or receptors in the body.

InChI:InChI=1/C11H6BrNO2/c1-6-8-4-7(12)2-3-10(8)15-11(14)9(6)5-13/h2-4H,1H3

Upstream product

• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 109-77-3 malononitrile 
• 105-56-6 ethyl 2-cyanoacetate 

Relevant academic research and scientific papers

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.

Iodine-mediated one-pot synthesis of 3-cyanocoumarins and 3-cyano-4-methylcoumarins

2-Hydroxybenzaldehydes 1a-e on reaction with malononitrile (2) in the presence of iodine as catalyst give 3-cyanocoumarins 3a-e in one step under thermal heating as well as under microwave irradiation. The latter conditions are much more efficient in terms of time (2-5 min) and yield as compared to the thermal conditions (2-2.5 h). Following a similar procedure, 3-cyano-4-methylcoumarins 3f-i were also prepared by the reaction of 2-hydroxyacetophenones 1f-i with 2.

Migratory decarboxylative coupling of coumarins: Synthetic and mechanistic aspects

On the move: Decarboxylative coupling of allyl 4-methyl-3-carboxycoumarins provides the products of γ-allylation of the methyl group rather than the typical regiospecific α-allylation. Mechanistic studies show that intramolecular proton transfer from the 4-methyl group to the 3-carboxylate allows allylation of the remote methyl group. The resulting 4-butenyl-3-carboxyl coumarin undergoes Pd0-catalyzed decarboxylation to provide the observed products (see scheme). Copyright

Tetrazole coumarin derivatives

A novel class of 3-tetrazole coumarins have anti-allergic activity. They are prepared by the action of ammonium azide on 3-cyano compounds.