76693-35-1

Usage

Uses

Used in Research and Technology:
6-Bromo-3-cyanocoumarin is used as a fluorescent probe for biological and chemical research, allowing for the labeling and tracking of various biological molecules and processes due to its blue light emission under UV radiation.
Used in Biomedical Applications:
In the field of medicine, 6-Bromo-3-cyanocoumarin has been studied for its potential use as a fluorescent tag for imaging and diagnosing cancerous tissues, leveraging its unique fluorescent properties to aid in early detection and analysis of diseases.

Upstream product

• 109-77-3 malononitrile 
• 1761-61-1 5-bromosalicyclaldehyde 
• 140-87-4 Cyanoacetohydrazide 
• 2199-90-8 ethyl 6-bromo-2-oxo-2H-chromene-3-carboxylate 
• 105-56-6 ethyl 2-cyanoacetate 
• 372-09-8 cyanoacetic acid 
• 79604-91-4 6-Bromo-2-imino-2H-chromene-3-carboxylic acid amide 

Downstream Products

• 2199-87-3 6-bromocoumarin-3-carboxylic acid 

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.

Coumarin derivatives act as novel inhibitors of human dipeptidyl peptidase III: Combined in vitro and in silico study

Dipeptidyl peptidase III (DPP III), a zinc-dependent exopeptidase, is a member of the metalloproteinase family M49 with distribution detected in almost all forms of life. Although the physiological role of human DPP III (hDPP III) is not yet fully elucida

Zirconium(IV) oxychloride: A simple and efficient catalyst for the synthesis of chromen-2-one derivatives

The present work explores a highly efficient, environmental friendly, green protocol for the synthesis of chromen-2-one derivatives (3a-m) by the condensation of salicylaldehydes with various active methylene compounds using zirconium (IV) oxychloride as catalyst. This is a convenient and rapid method for Knoevenagel condensation and this methodology offers several advantages including shorter reaction time, milder conditions, inexpensive catalyst, simple operational procedure and allowed to achieve the desired products in excellent yields. The structures of all the synthesized compounds were confirmed by spectral data.

PhI(OAc)2 mediated an efficient Knoevenagel reaction and their synthetic application for coumarin derivatives

A phenyliododiacetate (PhI(OAc)2) mediated an efficient and novel protocol for the Knoevenagel reaction has been successfully accomplished. A base free, simple and straightforward method afforded wide substrate scope and good functional group tolerance, having high yields (80–92%) under environmentally benign and mild reaction conditions.

ZIF-8 nanoparticles as an efficient and reusable catalyst for the Knoevenagel synthesis of cyanoacrylates and 3-cyanocoumarins

Zeolitic imidazolate framework (ZIF-8) particles with an average size of ca. 355 nm and a specific surface area of 1786 m2.g?1were used as an heterogenous catalyst for the Knoevenagel synthesis of α,β-unsaturated cyanoesters and 3-cy

The synthesis of coumarin derivatives using choline chloride/zinc chloride as a deep eutectic solvent

In this work, choline chloride/zinc chloride was employed as a deep eutectic solvent (DES) in the green synthesis of coumarin derivatives using Knoevenagel condensation. Coumarins are important organic structures with useful application in various fields.

A cost-effective and green aqueous synthesis of 3-substituted coumarins catalyzed by potassium phthalimide

An efficient procedure for the synthesis of various 2-imino-2H-chromene-3-carbonitriles, 2-oxo- 2H-chromene-3-carbonitriles as well as 2-oxo-2H-chromene-3-carboxylic acids is reported. It has been found that potassium phthalimide (PPI) catalyse the Knoevenagel condensation reaction of salicylaldehydes and activated β- dicarbonyl compounds efficiently under aqueous conditions at room temperature. This approach provides many merits such as high yields of products, clean, simple work-up, waste free, mild reaction conditions, commercially available organocatalyst, and the use of water as environmentally benign solvent.

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.

FeCl3-catalyzed cascade reaction: An efficient approach to functionalized coumarin derivatives

An efficient and environmentally benign synthesis of 3-substituted or 3,4-disubstituted coumarins was accomplished via iron(III) chloride-catalyzed cascade reactions of salicylaldehydes and activated methylene compounds. The reaction preceded cleanly under mild reaction conditions to provide the desired coumarin derivatives in good to excellent yields.

An efficient one-pot synthesis of coumarins mediated by propylphosphonic anhydride (T3P) via the Perkin condensation

An efficient one-pot synthesis of coumarins mediated by T3P, a mild and low toxic peptide coupling agent, via the Perkin condensation has been demonstrated.