566206-48-2

Basic information

• Product Name: 2H-1-Benzopyran-2-one, 6-bromo-7-hydroxy-4-(2-phenyl-1,3-dioxolan-4-yl)-
• CAS NO: 566206-48-2
• Molecular Formula: C18H13BrO5
• Molecular Weight: 389.202
• Mol File: 566206-48-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2H-1-Benzopyran-2-one, 6-bromo-7-hydroxy-4-(2-phenyl-1,3-dioxolan-4-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-2-one, 6-bromo-7-hydroxy-4-(2-phenyl-1,3-dioxolan-4-yl)-(566206-48-2)
• EPA Substance Registry System: 2H-1-Benzopyran-2-one, 6-bromo-7-hydroxy-4-(2-phenyl-1,3-dioxolan-4-yl)-(566206-48-2)

Safety Data

• Hazardous Substances Data: 566206-48-2(Hazardous Substances Data)

Upstream product

• 566206-44-8 6-bromo-4-chloromethyl-7-acetyloxycoumarin 
• 223420-33-5 6-bromo-4-(chloromethyl)-7-hydroxy-2H-chromen-2-one 
• 566206-46-0 6-bromo-7-hydroxy-4-vinylcoumarin 
• 100-52-7 benzaldehyde 
• 566206-47-1 6-bromo-4-(1,2-dihydroxyethyl)-7-hydroxycoumarin 

Downstream Products

• 100-52-7 benzaldehyde 
• 566206-47-1 6-bromo-4-(1,2-dihydroxyethyl)-7-hydroxycoumarin 
• 1221557-65-8 4-[-8-[bis(methoxycarbonylmethyl)aminomethyl]-6-bromo-7-hydroxycoumarin-4-yl]-2-phenyl-1,3-dioxolane 

Relevant articles and documents

[8-[Bis(carboxymethyl)aminomethyl]-6-bromo-7-hydroxycoumarin-4-yl]methyl Moieties as photoremovable protecting groups for compounds with COOH, NH 2, OH, and C-O functions

We introduce a variant of coumarin-based photoactivatable protecting groups and use it exemplarily for caging of a carboxylic acid, an amine, a phenol, and a carbonyl compound. The caged compounds are efficiently photolyzed at long-wavelength UV/vis irradiation. Compared to the corresponding (6-bromo-7-hydroxycoumarin-4-yl)methyl (Bhc) derivatives, the novel coumarin-type caged compounds are distinguished by (i) dramatically increased solubilities in aqueous buffers, (ii) lower pKa values of the C7 hydroxyl of the coumarin chromophore, thus permitting efficient photorelease at lower pH, and (iii) higher photolysis quantum yields in the case of photoprotected carbonyl compounds. The primary step of the photocleavages occurs with rate constants of about 109 s-1.