95302-25-3

Upstream product

• 150-76-5 4-methoxy-phenol 
• 2211-94-1 2,3-epoxypropyl p-methoxyphenyl ether 
• 95302-25-3 (+/-)-1-bromo-3-(4-methoxyphenyloxy)-2-propanol 
• 3132-64-7 1,2-Epoxy-3-bromopropane 

Downstream Products

• 95302-25-3 (R)-1-Bromo-3-(4-methoxy-phenoxy)-propan-2-ol 
• 140647-17-2 Acetic acid (S)-1-bromomethyl-2-(4-methoxy-phenoxy)-ethyl ester 

Relevant academic research and scientific papers

Green protocol for the synthesis of vicinal-halohydrins from oxiranes using the [Bmim]PF6/LiX reagent system

Epoxides undergo rapid ring-opening with lithium halides in [bmim]PF 6 or [bmim]BF4 ionic liquids under mild and neutral conditions to afford the corresponding vic-halohydrins in high to quantitative yields. The epoxides show enhanced reactivity in ionic liquids thereby reducing reaction times and improving the yields significantly. The recovered ionic liquid can be reused in three to four subsequent runs with consistent activity.

Design, synthesis and biological evaluation of novel 1,2,3-triazolyl β -hydroxy alkyl/carbazole hybrid molecules

The design, synthesis and biological study of several novel 1,2,3-triazolyl β -hydroxy alkyl/carbazole hybrid molecules as a new type of antifungal agent has been described. In this synthesis, the N-alkylation reaction of carbazol-9-ide potassium salt with 3-bromoprop-1-yne afforded 9-(prop-2-ynyl)-9H-carbazole. The ‘Click’ Huisgen cycloaddition reaction of 9-(prop-2-ynyl)-9H-carbazole with diverse β -azido alcohols in the presence of copper-doped silica cuprous sulphate led to target molecules in excellent yields. The in vitro antifungal and antibacterial activities of title compounds were screened against various pathogenic fungal strains, Gram-positive and/or Gram-negative bacteria. In particular, 1-(4-((9H-carbazol-9-yl) methyl)-1H-1,2,3-triazol-1-yl)-3-butoxypropan-2-ol (10e) proved to have potent antifungal activity against all fungal tests compared with fluconazole and clotrimazole as studied reference drugs. Our molecular docking analysis revealed an appropriate fitting and a potential powerful interaction between compound 10e and an active site of the Mycobacterium P450DM enzyme. The strong hydrogen bondings between β -hydroxyl and ether groups in 10e were found to be the main factors that drive the molecule to fit in the active site of enzyme. The in silico pharmacokinetic studies were used for a better description of 10a–10n as potential lead antifungal agents for future investigations.

'Click synthesis' of some novel o-substituted oximes containing 1,2,3-triazole-1,4-diyl residues as new analogs of β-adrenoceptor antagonists

The 'click synthesis' of some novel O-substituted oximes, 7a-7t, which contain 1,2,3-triazolediyl residues, as new analogs of β-adrenoceptor antagonists is described (Schemes 1-4). The synthesis of these compounds was achieved in four to five steps. The formation of oximes of 9H-fluoren-9-one and benzophenone, i.e., 9a and 9b, respectively, followed by their reaction with propargyl bromide, afforded O-propargyl oximes 10a and 10b, respectively, which by a subsequent CuI-catalyzed Huisgen cycloaddition with prepared β-azido alcohols 11a-11j (Schemes 2 and 3), led to the target compounds 7a-7t in good yields. Copyright

Protective opening of epoxide using pivaloyl halides under catalyst-free conditions

An efficient and environmentally benign protocol for protective opening of epoxide (POE) with pivaloyl halides in solvent-free conditions and in aqueous media under catalyst-free conditions has been developed. The green reaction conditions, simple work-up procedures, high yields and broad scope of the reaction illustrate the good synthetic utility of this method. The key advantages of the reaction are regioselectivity and reconvertability of products into their prior epoxides in the presence of mild reaction conditions.

Allyltin tribromide: A versatile reagent involved in the ring-opening of epoxides

This paper presents a versatile reagent for epoxide cleavage. The allyltin tribromide could act as a novel and easily prepared allylation reagent and halide atom donor to convert epoxides to the corresponding homoallyl alcohols and halohydrins in high yields with excellent regioselectivities under mild reaction conditions, respectively. It could also act as a Lewis acid to catalyze the ring opening reactions of epoxides with alcohols.

Monobromoborane-dimethyl sulfide - A highly promising reagent for the regio- and chemoselective brominative cleavage of terminal epoxides into vicinal bromohydrins

Monobromoborane?dimethyl sulfide (BH2Br?SMe2) is a highly regio- and chemoselective reagent useful for the brominative cleavage of the epoxy moiety into bromohydrins in the presence of alkenes, alkynes, ethers, acetals, ketals, and acetonides at 0°C, besides being an excellent hydroborating reagent. Several reactive functional groups, such as chloride, ketones, esters, nitriles, nitros, and thioethers, have been accommodated during such transformations. Although the reduction of acetophenone was completely suppressed at ?25°C, 4-chlorobenzaldehyde still underwent 12?13% reduction of an aldehydic group. CSIRO 2007.

Highly facile biomimetic regioselective ring opening of epoxides to halohydrins in the presence of β-cyclodextrin

Highly regioselective ring opening of epoxides to halohydrins has been carried out in impressive yields with hydrogen and lithium halides in presence of β-cyclodextrin using water as solvent.

The halogen-mediated opening of epoxides in the presence of pyridine-containing macrocycles

The ring opening of epoxides with elemental iodine and bromine in the presence of three pyridine-containing macrocyclic diamides as new catalysts affords vicinal iodo alcohols and bromo alcohols in high yields. This new procedure occurs regioselectively under mild conditions in various aprotic solvents. The catalysts are easily recovered and can be reused several times.

RESOLUTION OF RACEMIC O-(4-METHOXYPHENYL)GLYCIDOL

Racemic O-(4-methoxyphenyl)glycidol has been resolved in three steps by employing lipase mediated kinetic acylation of the halohydrin intermediates.