CAS 13922-41-3: 1-Naphthylboronic acid

This Thermo Scientific Chemicals brand product was originally part of the Acros Organics product portfolio. Some documentation and label information may refer to the legacy brand. The original Acros Organics product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

1-Naphthylboronic acid, min. 97%

Naphthalene-1-boronic acid

1-Naphthaleneboronic acid is a compound that belongs to the class of boronic acids. It is a fluorescent probe for studying the Mcl-1 protein and has been shown to bind to fatty acid targets in biological studies. 1-Naphthaleneboronic acid has been synthesized in an asymmetric synthesis with palladium as a catalyst and hydrogen fluoride as the reducing agent. The compound can be reversibly converted between its boronic acid and amine form, which may contribute to its light emission properties. In addition, 1-Naphthaleneboronic acid has been shown to have transport properties and hydrolysis by hydrochloric acid.

Applications B-1-Naphthalenyl-boronic Acid is a useful synthetic intermediate. It is a reagent used to synthesize potassium aryltrifluoroborates which is a convenient precursor of arylboron difluoride lewis acids. It can also be used to prepare high yields of biaryls via Suzuki coupling. References Vedejs, E., et al.: J. Org. Chem., 60, 3020 (1995); Larhed, M., et al.: Tetrahedron Lett., 37, 8219 (1996); Singh, R., et al.: 7, 1829 (2005)

1-Naphthaleneboronic acid is a very useful building block for introduction of a naphthyl group through cross-coupling protocols. It is useful in the synthesis of polyaromatic hydrocarbons utilizing the Suzuki reaction. This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.