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CAS 377780-72-8

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(2-Bromomethylphenyl)boronic acid, pinacol ester

Description:
(2-Bromomethylphenyl)boronic acid, pinacol ester is an organoboron compound characterized by the presence of a boronic acid functional group and a bromomethylphenyl moiety. This compound typically exhibits a white to off-white solid appearance and is soluble in organic solvents such as dichloromethane and ethanol, but may have limited solubility in water due to the hydrophobic nature of the aromatic ring. The pinacol ester formation enhances the stability of the boronic acid, making it more suitable for various synthetic applications, particularly in cross-coupling reactions like Suzuki-Miyaura coupling. The bromine atom serves as a good leaving group, facilitating nucleophilic substitution reactions. Additionally, the compound can participate in various transformations due to the reactivity of the boron atom, which can form complexes with nucleophiles. Its applications are significant in organic synthesis, medicinal chemistry, and materials science, where it can be utilized in the development of pharmaceuticals and advanced materials. Proper handling and storage are essential due to potential reactivity and the need for safety precautions when working with organoboron compounds.
Formula:C13H18BBrO2
InChI:InChI=1/C13H18BBrO2/c1-12(2)13(3,4)17-14(16-12)11-8-6-5-7-10(11)9-15/h5-8H,9H2,1-4H3
SMILES:CC1(C)C(C)(C)OB(c2ccccc2CBr)O1
Synonyms:
  • 2-[2-(Bromomethyl)Phenyl]-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane
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