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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.
Boronic acids are used extensively in organic chemistry as chemical building blocks and intermediates predominantly in the Suzuki coupling. A key concept in its chemistry is transmetallation of its organic residue to a transition metal. The compound bortezomib with a boronic acid group is a drug used in chemotherapy.
Pinacolborane is used in borylation, a form of C-H activation. [8] [9] Dehydrogenation of pinacolborane affords dipinacolatodiborane (B 2 pin 2): [10] 2 ...
Borinic acid, also known as boronous acid, is an oxyacid of boron with formula H 2 BOH. Borinate is the associated anion of borinic acid with formula H 2 BO −; however, being a Lewis acid, the form in basic solution is H 2 B(OH) − 2. Borinic acid can be formed as the first step in the hydrolysis of diborane: [1] BH 3 + H 2 O → H 2 BOH + H 2
Compounds of the type BR n (OR) 3-n are called borinic esters (n = 2), boronic esters (n = 1), and borates (n = 0). Boronic acids are key to the Suzuki reaction. Trimethyl borate, debatably not an organoboron compound, is an intermediate in sodium borohydride production.
The boron atom of a boronic ester or acid is sp 2 hybridized possessing a vacant p orbital, enabling these groups to act as Lewis acids. The C–B bond of boronic acids and esters are slightly longer than typical C–C single bonds with a range of 1.55-1.59 Å.
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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.