223420-41-5

Basic information

• Product Name: 6-bromo-7-hydroxy-4-(hydroxymethyl)-2H-chromen-2-one
• Synonyms: 6-bromo-7-hydroxy-4-(hydroxymethyl)-2H-chromen-2-one;6-Bromo-7-hydroxy-4-hydroxymethylcoumari;6-Bromo-7-hydroxy-4-(hydroxymethyl)coumarin
• CAS NO: 223420-41-5
• Molecular Formula: C₁₀H₇BrO₄
• Molecular Weight: 271.06418
• Mol File: 223420-41-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 264 °C
• Appearance: /
• CAS DataBase Reference: 6-bromo-7-hydroxy-4-(hydroxymethyl)-2H-chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromo-7-hydroxy-4-(hydroxymethyl)-2H-chromen-2-one(223420-41-5)
• EPA Substance Registry System: 6-bromo-7-hydroxy-4-(hydroxymethyl)-2H-chromen-2-one(223420-41-5)

Safety Data

• Hazardous Substances Data: 223420-41-5(Hazardous Substances Data)

Usage

General Description

6-bromo-7-hydroxy-4-(hydroxymethyl)-2H-chromen-2-one, also known as bromocresol green, is a synthetic dye and pH indicator commonly used in laboratory settings. It is a member of the triphenylmethane chemical class and is typically used as a pH indicator in applications such as titrations, where it changes color depending on the acidity of the solution. Bromocresol green has a yellow color in acidic conditions and a blue color in alkaline conditions, with a transition range of pH 3.8 to 5.4. Additionally, researchers have investigated its potential as an anti-inflammatory and anti-cancer agent due to its biological activity. Overall, 6-bromo-7-hydroxy-4-(hydroxymethyl)-2H-chromen-2-one is a versatile compound with various applications in chemistry and potential therapeutic uses.

Upstream product

• 1332870-78-6 C₄₅H₇₄BrNO₈ 
• 1221557-61-4 N-[(6-bromo-7-hydroxycoumarin-4-yl)methoxycarbonyl]dopamine 
• 1221557-59-0 (6-bromo-7-hydroxycoumarin-4-yl)methyl phenylacetate 
• 640721-06-8 3-O-[[(6-bromo-7-hydroxycoumarin-4-yl)methoxy]carbonyl]-1,2-di-O-octanoylglycerol 
• 640720-93-0 carbonic acid 6-bromo-7-hydroxy-2-oxo-2H-chromen-4-ylmethyl ester 2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester 
• 640721-01-3 phenyl (6-bromo-7-hydroxycoumarin-4-yl)methyl carbonate 

Downstream Products

• 1414975-53-3 C₄₂H₅₁BrN₁₂O₁₆S 
• 1414975-48-6 C₂₃H₁₈BrN₃O₉S 
• 1414975-63-5 C₁₉H₁₅BrN₂O₇S 
• 1414975-61-3 C₂₃H₂₃BrN₂O₇S 
• 1414975-64-6 C₂₂H₁₈BrN₃O₆S 
• 425431-08-9 4-{4-[(benzyl-methyl-amino)-methyl]-[1,3]dioxolan-2-yl}-6-bromo-7-hydroxy-chromen-2-one 
• 425431-12-5 6-bromo-7-hydroxy-4-(2-phenyl-tetrahydro-[1,3]dioxolo[4,5-e][1,3]dioxepin-6-yl)-chromen-2-one 
• 640721-04-6 (6-bromo-7-(methoxymethoxy)-2-oxo-2H-chromen-4-yl)methyl(4-nitrophenyl) carbonate 
• 485318-64-7 (6-bromo-7-hydroxycoumarin-4-yl)methyl 4-nitrophenyl carbonate 
• 640721-01-3 phenyl (6-bromo-7-hydroxycoumarin-4-yl)methyl carbonate 

Relevant articles and documents

Control of an Unusual Photo-Claisen Rearrangement in Coumarin Caged Tamoxifen through an Extended Spacer

The use of coumarin caged molecules has been well documented in numerous photocaging applications including for the spatiotemporal control of Cre-estrogen receptor (Cre-ERT2) recombinase activity. In this article, we report that 4-hydroxytamoxifen (4OHT) caged with coumarin via a conventional ether linkage led to an unexpected photo-Claisen rearrangement which significantly competed with the release of free 4OHT. The basis for this unwanted reaction appears to be related to the coumarin structure and its radical-based mechanism of uncaging, as it did not occur in ortho-nitrobenzyl (ONB) caged 4OHT that was otherwise linked in the same manner. In an effort to perform design optimization, we introduced a self-immolative linker longer than the ether linkage and identified an optimal linker which allowed rapid 4OHT release by both single-photon and two-photon absorption mechanisms. The ability of this construct to actively control Cre-ERT2 mediated gene modifications was investigated in mouse embryonic fibroblasts (MEFs) in which the expression of a green fluorescent protein (GFP) reporter dependent gene recombination was controlled by 4OHT release and measured by confocal fluorescence microscopy and flow cytometry. In summary, we report the implications of this photo-Claisen rearrangement in coumarin caged compounds and demonstrate a rational linker strategy for addressing this unwanted side reaction.

[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.