4950-06-5

Usage

InChI:InChI=1/C7H6Br2O3/c8-5-3(2-10)1-4(11)7(12)6(5)9/h1,10-12H,2H2

Upstream product

• 14045-41-1 2,3-dibromo-4,5-dihydroxybenzylaldehyde 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 121-33-5 vanillin 
• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 
• 2973-75-3 5,6-dibromo-4-hydroxy-3-methoxybenzaldehyde 
• 40089-29-0 dipotassium 2,3-dibromo-5-hydroxybenzyl-1',4-disulfate 

Downstream Products

• 100676-08-2 methylrhodomelol 
• 100676-10-6 rhodomelol 
• 54502-93-1 3,4-dibromo-5-(ethoxymethyl)benzene-1,2-diol 
• 70625-32-0 3,4-Dibrom-5,5'-methylendibrenzcatechin 
• 70625-30-8 5-(2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxybenzyl)-3,4-dibromobenzene-1,2-diol 
• 14045-42-2 3,4-dibromo-5-(methoxymethyl)benzene-1,2-diol 
• 65487-76-5 2,2′,3,3′-tetrabromo-4,4′,5,5′-tetrahydroxydiphenylmethane 
• 65487-78-7 3,4,3',4'-Tetrabrom-5,5'-methylendibrenzcatechin-tetramethylether 

Relevant academic research and scientific papers

Total synthesis of the biologically active, naturally occurring 3,4-dibromo-5-[2-bromo-3,4-dihydroxy-6-(methoxymethyl)benzyl]benzene-1,2-diol and regioselective O-demethylation of aryl methyl ethers

3,4-Dibromo-5-[2-bromo-3,4-dihydroxy-6-(methoxymethyl)benzyl]benzene-1, 2-diol (2), a natural product, has been synthesized for the first time starting from (3-bromo-4,5-dimethoxyphenyl)methanol (5) in five steps and with an overall yield of 34%. The reaction of some methoxymethyl-substituted aryl methyl ethers with BBr3, followed by the addition of MeOH, afforded the corresponding methoxymethyl-substituted arylphenols in high yields.

In-vitro cytotoxic activities of the major bromophenols of the red alga Polysiphonia lanosa and some novel synthetic isomers

Bioassay-guided fractionation was applied to the cytotoxic chloroform fraction of the red alga Polysiphonia lanosa. The major compounds of the most active fraction were identified using GLC-MS analysis as lanosol (1), methyl, ethyl, and n-propyl ethers of lanosol (1a, 1b, and 1c, respectively), and aldehyde of lanosol (2), although 1b appears to be an artifact arising during the fractionation procedure. These compounds and other known bromophenols were synthesized in addition to four novel isomers (3, 3a-c). The cytotoxic activities of all the synthetic compounds were determined against DLD-1 cells using the MTT assay. Compounds with IC50 50 = 1.72 and 0.80 μmol, respectively), and its effect on the cell cycle was studied using flow cytometry.

Synthesis of some hydroxymethylbromophenols of marine origin

The hydroxymethylbromophenols 5, 7 and 9, isolated from marine source have been prepared in good yield.The bromo derivatives 1 and 2 of vanillin are demethylated to 4 and 6 which on borohydride reduction furnish 5 and 7 respectively.The dibromo-p-cresol (3) is oxidised to the aldehyde 8 which on borohydride reduction affords 9.