109737-57-7Relevant academic research and scientific papers
Trace Level Quantification of Derivatized Boronic Acids by LC/MS/MS
Baldwin, Aaron F.,North, Robert,Eisenbeis, Shane
, (2019)
Boron-containing compounds are often controlled as potentially mutagenic impurities based on ICH M7 guidance in drug substances. Herein, we describe a simple method to derivatize a subset of organoborons, non-nitrogen-containing aryl boronic acids, in order to quantify trace levels remaining in a drug substance using LC/MS/MS. Through this derivatization we are able to increase the sensitivity, demonstrate linearity, and spiked analyte recovery in matrix down to low parts per million (ppm) levels. The feasibility of this method is proven as three different examples are described, two in which one boronic acid may be present in a drug substance and one where two boronic acids may be present in the final product.
Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids
Marciasini, Ludovic D.,Richard, Jimmy,Cacciuttolo, Bastien,Sartori, Guillaume,Birepinte, Melodie,Chabaud, Laurent,Pinet, Sandra,Pucheault, Mathieu
, p. 164 - 171 (2018/12/05)
Owing to the unusual reactivity of dialkylamine-borane complexes, a methodology was developed to simply access boronic acids. The intrinsic instability of magnesium aminoborohydride was tweaked into a tandem dehydrogenation borylation sequence. Proceeding via an autocatalytic cycle, amineborane dehydrogenation was induced by a variety of Grignard reagents. Overall, addition of the organomagnesium species onto specially designed dialkylamine-borane complexes led to a variety of boronic acids in high yields. In addition, the reaction can be performed under Barbier conditions, on a large scale.
A Green Alternative for the Conversion of Arylboronic Acids/Esters into Phenols Promoted by a Reducing Agent, Sodium Sulfite
Castro-Godoy, Willber D.,Schmidt, Luciana C.,Argüello, Juan E.
supporting information, p. 3035 - 3039 (2019/05/15)
Hydroxylation of arylboronic acids and arylboronic esters using sodium sulfite and oxygen as the source of ultimate oxidant proceeds rapidly in water under transition metal-free conditions. This remarkable mild and environmentally benign protocol represents a green alternative to synthesize phenols using inexpensive starting materials in a simple methodology. This new application for sodium sulfite shows a wide tolerance of functional groups, and it is compatible with oxidizable functionalities.
Trace Level Quantification of Derivatized Boronic Acids by LC/MS/MS
Baldwin, Aaron F.,North, Robert,Eisenbeis, Shane
, p. 88 - 92 (2019/01/24)
Boron-containing compounds are often controlled as potentially mutagenic impurities based on ICH M7 guidance in drug substances. Herein, we describe a simple method to derivatize a subset of organoborons, non-nitrogen-containing aryl boronic acids, in order to quantify trace levels remaining in a drug substance using LC/MS/MS. Through this derivatization we are able to increase the sensitivity, demonstrate linearity, and spiked analyte recovery in matrix down to low parts per million (ppm) levels. The feasibility of this method is proven as three different examples are described, two in which one boronic acid may be present in a drug substance and one where two boronic acids may be present in the final product.
Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates
Close, Adam J.,Kemmitt, Paul,Emmerson, Matthew K.,Spencer, John
, p. 9125 - 9131 (2015/03/05)
A library of over 20, mainly aryl or heteroaryl, N-methyliminodiacetic acid (MIDA) boronates have been synthesised. A rapid microwave-mediated (MW) method (5-10 min) has been developed using polyethylene glycol 300 (PEG 300) as solvent. However, acetonitr
