6642-34-8

Usage

InChI:InChI=1/C8H7BrO3/c9-6-2-8-7(11-4-12-8)1-5(6)3-10/h1-2,10H,3-4H2

Upstream product

• 811-98-3 d⁽⁴⁾-methanol 
• 124-41-4 sodium methylate 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 108-98-5 thiophenol 

Downstream Products

• 144412-83-9 1-<2-(Hydroxymethyl)-4,5-(methylenedioxy)phenyl>-2-cyclohexen-1-ol 
• 86449-38-9 6-Brompiperonylbenzylether 
• 82792-83-4 -3,4-methylenedioxybenzyl alcohol 
• 34679-09-9 1-bromo-2-(methoxymethyl)-4,5-(methylenedioxy)benzene 
• 82792-87-8 (6-bromobenzo[d][1,3]dioxol-5-yl)methanethiol 
• 495-76-1 piperonol 
• 79422-40-5 6,6'-bis(hydroxymethyl)-5,5'-bi-1,3-benzodioxole 
• 165674-17-9 (6-bromo-2H-benzo<3,4-d>-1,3-dioxolan-5-yl)methyl (2S,3R)-3-<(4S,5R)-5-<(1Z)-2-aza-2-(phenylmethoxy)vinyl>-2,2-dimethyl(1,3-dioxolan-4-yl)>-3-(methoxymethoxy)-2-(1,1,2,2-tetramethyl-1-silapropoxy)propanoate 
• 473253-66-6 benzo[1,3]dioxol-5-yl-(6-(hydroxymethyl)benzo[1,3]dioxol-5-yl)methanol 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 880104-84-7 4-methyl-benzenesulfinic acid 6-bromo-benzo[1,3]dioxol-5-ylmethyl ester 
• 937792-53-5 5-benzyl-6-ethynyl-benzo[1,3]dioxole 
• 14944-34-4 3-hydroxymethyl-6,7-methylenedioxy-1-(3,4-methylenedioxyphenyl)naphthalene-2-carboxylic acid lactone 
• 473253-65-5 3,4-dimethoxybenzyl-(6-formylbenzo[1,3]dioxol-5-yl)methanone 

Relevant academic research and scientific papers

Regioselective cleavage reaction of the aromatic methylenedioxy ring. VI. Synthesis of phenothiazine analogues by using the cleavage reaction with sodium methoxide-thiols in dimethyl sulfoxide and evaluation of their biological activities

The reactions of aromatic methylenedioxy compounds containing electron- withdrawing groups with sodium methoxide-thiols in dimethyl sulfoxide gave 3- and 4-hydroxybenzene derivatives in good yield by regioselective attack of the thiolate ions on the methylenedioxy ring. The formation mechanism and the reactivity of thiolate ions in the cleavage reaction of the methylenedioxy ring are discussed. Various biologically active compounds, 32a, 32d, 36b, 38h, 41b and 44-47, were prepared from the 4-hydroxybenzene derivatives and their Ca2+ antagonistic activities were evaluated. Among these compounds, 2-(2-bromophenylthiomethoxy)-10-(2-diethylaminoacetyl)-3-methoxyphenothiazi ne (46) showed the most potent Ca2+ antagonistic activity. Biological activity could be conveniently evaluated by measurement of the peak height of the vanadyl ion (+4 oxidation ion) signal produced by redox reaction between the phenothiazine derivatives and vanadate ion +5 oxidation ion) with ESR spectroscopy.

REGIOSELECTIVE CLEAVAGE REACTION OF THE METHYLENEDIOXY RING IN AROMATIC COMPOUNDS CONTAINING ELECTRONWITHDRAWING GROUPS WITH SODIUM ALKOXIDES-ALCOHOLS IN DIMETHYL SULFOXIDE

The reaction of 6-bromopiperonal (1) with sodium alkoxides (MeONa or PhCH2ONa)-alcohols (MeOH or PhCH2OH), and sodium alkoxides (MeONa, PhCH2ONa or PhONa)-phenol (PhOH) in dimethyl sulfoxide gave 3-hydroxybenzene derivatives (3, 5 and 6) and 4-hydroxybenzene derivative (4), respectively.The reactivity and formational mechanism of various nucleophilic reagents (alkoxide anions) formed from the alcohols and phenol by sodium alkoxides in the regioselective cleavage reactions are discussed.

Cleavage of Methylenedioxy Ring. II. Cleavage with Sodium Phenoxide and Methoxide in Dimethyl Sulfoxide

Regioselective cleavage of the methylenedioxy ring in piperonals (1, 6, and 7) and 3,4-methylenedioxynitrobenzenes (8 and 9) by oxide ions in dimethyl sulfoxide was achieved: the 4-hydroxybenzene derivatives (2, 10-13, and 22) were obtained with the phenoxide ion, while the 3-hydroxybenzene derivatives (4, 18-21, 23, 26, and 29) were obtained with the methoxide or benzyloxide ion.Keywords - cleavage of methylenedioxy ring; regioselectivity; piperonals; 3,4-methylenedioxynitrobenzenes; sodium phenoxide; sodium methoxide; dimethyl sulfoxide; 3-hydroxybenzene derivatives; 4-hydroxybenzene derivatives; NMR spectra