88861-40-9

Upstream product

• 2747-05-9 4-methylumbelliferyl acetate 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 88861-36-3 4-formyl-2-oxo-2H-chromen-7-yl acetate 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 88861-47-6 Benzoic acid 7-acetoxy-2-oxo-2H-chromen-4-ylmethyl ester 

Relevant academic research and scientific papers

Studies on Stable Diazoalkanes as Potential Fluorogenic Reagents. I. 7-Substituted 4-Diazomethylcoumarins

As a new type of stable diazoalkane, 4-diazomethylcoumarins (4) bearing various 7-substituents were prepared for potential use in introducing fluorophores into acidic substances.Selenium dioxide oxidation of 4-methylcoumarins to the corresponding coumarin-4-carbaldehydes followed by triethylamine-mediated Bamford-Stevens reaction of their tosylhydrazones readily gave 4 as excellently stable and almost non-fluorescent crystals, exhibiting characteristic diazomethyl 1H- and 13C-nuclear magnetic resonance signals.Labeling reactions of carboxylic acids using 4 in refluxing chloroform in the presence of silica gel catalyst gave excellent yields of fluorescent coumarin-4-ylmethyl esters.In view of their stability, accessibility and fluorogenicity, these compounds (4), especially those bearing 7-methoxy and 7-acetyloxy substituents, should be practically useful fluorogenic reagents for carboxylic acids.Keywords - stable diazoalkane; 4-diazomethylcoumarin; selenium dioxide oxidation; Bamford-Stevens reaction; diazomethyl NMR; silica gel-catalyzed reaction; fluorescent esterification of carboxylic acid; coumarin-4-ylmethyl ester fluorescence