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Examples of boronic esters Boronic ester Diol Structural formula Molar mass CAS number Boiling point (°C) Allylboronic acid pinacol ester: pinacol: 168.04: 72824-04-5: 50–53 (5 mmHg) Phenyl boronic acid trimethylene glycol ester: trimethylene glycol: 161.99: 4406-77-3: 106 (2 mm Hg) Diisopropoxymethylborane: isopropanol: 144.02 86595-27-9: ...
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 remove water. PhB(OH) 2 + 2 ROH ⇌ PhB(OR) 2 + 2 H 2 O
Bisphenol A is difunctional and used to produce epoxy resin and polycarbonate. 4-tert-Butylphenol is monofunctional and so in polymer science terms, bisphenol A is a polymer chain extender but 4-tert-butylphenol is a chain stopper or sometimes called endcapper. It is thus use to control molecular weight by limiting chain growth.
It has the formula [(CH 3) 4 C 2 O 2 B] 2; the pinacol groups are sometimes abbreviated as "pin", so the structure is sometimes represented as B 2 pin 2. It is a colourless solid that is soluble in organic solvents. It is a commercially available reagent for making pinacol boronic esters for organic synthesis.
Pinacol is a branched alcohol which finds use in organic syntheses. It is a diol that has hydroxyl groups on vicinal carbon atoms. A white solid that melts just above room temperature, pinacol is notable for undergoing the pinacol rearrangement in the presence of acid and for being the namesake of the pinacol coupling reaction .
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Basic heteroaromatic boronic acids (boronic acids that contain a basic nitrogen atom, such as 2-pyridine boronic acid) display additional protodeboronation mechanisms. [4] A key finding shows the speciation of basic heteroaromatic boronic acids to be analogous to that of simple amino acids , with zwitterionic species forming under neutral pH ...