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PhB(OH) 2 + Br 2 + H 2 O → PhBr + B(OH) 3 + HBr. Boronic esters result from the condensation of boronic acids with alcohols. This transformation is simply the replacement of the hydroxyl group by alkoxy or aryloxy groups. [4] This reversible reaction is commonly driven to product by the use of Dean-Stark apparatus or a dehydration agent to ...
Boronic acids are known to bind to active site serines and are part of inhibitors for porcine pancreatic lipase, [2] subtilisin [3] and the protease Kex2. [4] Furthermore, boronic acid derivatives constitute a class of inhibitors for human acyl-protein thioesterase 1 and 2, which are cancer drug targets within the Ras cycle. [5]
Benzilic acid can be prepared by heating a mixture of benzil, ethanol, and potassium hydroxide. Another preparation, performed by Liebig in 1838, is the dimerization of benzaldehyde , to benzil , which is transformed to the product by the benzilic acid rearrangement reaction.
The mechanism of organotrifluoroborate-based Suzuki-Miyaura coupling reactions has recently been investigated in detail. The organotrifluoroborate hydrolyses to the corresponding boronic acid in situ, so a boronic acid can be used in place of an organotrifluoroborate, as long as it is added slowly and carefully. [7] [8]
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Anisyl alcohol (4-methoxybenzyl alcohol) is an organic compound with the chemical formula CH 3 OC 6 H 4 CH 2 OH. [1] It is a colorless liquid that is used as a fragrance and flavorant. It occurs naturally but is produced by reduction of the aldehyde or carboxylic acid. [2] It reacts with hydrogen bromide to give 4-methoxylbenzyl bromide. [3]
Boroxine (B 3 H 3 O 3) is a 6-membered heterocyclic compound composed of alternating oxygen and singly-hydrogenated boron atoms. Boroxine derivatives (boronic anhydrides) such as trimethylboroxine and triphenylboroxine also make up a broader class of compounds called boroxines. [1]
The reaction of boron trichloride with alcohols was reported in 1931, and was used to prepare dimethoxyboron chloride, B(OCH 3) 2 Cl. [3] Egon Wiberg and Wilhelm Ruschmann used it to prepare tetrahydroxydiboron by first introducing the boron–boron bond by reduction with sodium and then hydrolysing the resulting tetramethoxydiboron, B 2 (OCH 3) 4, to produce what they termed sub-boric acid. [4]