CAS 109737-57-7 | 6-Methyl-2-phenyl-1,3,6,2-dioxazaborocane-4,8-dione

6-Methyl-2-phenyl-1,3,6,2-dioxazaborocane-4,8-dione is an organoboron reagent with a molecular formula of C₁₁H₁₂BNO₄. Its chemical structure contains a benzene ring and a methyliminodiacetate (MIDA) group, and it belongs to the derivative esters of phenylboronic acid. Its CAS number is 109737-57-7.

Uses:

As a stable boronation reagent, 6-Methyl-2-phenyl-1,3,6,2-dioxazaborocane-4,8-dione is widely used in Suzuki-Miyaura coupling reactions. It can introduce phenylboronic acid groups under mild conditions, avoiding the problem of easy oxidation or hydrolysis of traditional boric acid. Its MIDA ester structure can improve reaction selectivity and substrate compatibility, and is suitable for the synthesis of complex molecules (such as drug intermediates and natural products).

Method of Preparation:
A common synthetic method is to synthesize phenylboronic acid methyliminodiacetate using ester exchange reaction of imines. The specific synthesis steps include:
Reacting methyl p-tolylboronate with ethyl nitroso-2-acetamidoacetate to form ethyl imino-2-(p-tolylboronic acid) acetate.
Reacting the ethyl imino-2-(p-tolylboronic acid) acetate with another esterifying reagent, such as ethyl bromoacetate or n-butanol, to produce the end product 6-Methyl-2-phenyl-1,3,6,2-dioxazaborocane-4,8-dione .

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