17604-70-5

Basic information

• Product Name: 2-(((methoxy)imino)methyl)phenylboronic acid
• Synonyms: 2-(((methoxy)imino)methyl)phenylboronic acid
• CAS NO: 17604-70-5
• Molecular Weight: 178.983
• Mol File: 17604-70-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(((methoxy)imino)methyl)phenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(((methoxy)imino)methyl)phenylboronic acid(17604-70-5)
• EPA Substance Registry System: 2-(((methoxy)imino)methyl)phenylboronic acid(17604-70-5)

Safety Data

• Hazardous Substances Data: 17604-70-5(Hazardous Substances Data)

Usage

Structure

A phenyl ring attached to a boron atom with a methoxyimino group (a methoxy group and an imine functional group) attached to the phenyl ring

Type of compound

Boronic acid derivative

Usage

A versatile building block for the synthesis of various biologically active molecules and pharmaceuticals in organic synthesis and medicinal chemistry
Reagent in the Suzuki-Miyaura cross-coupling reaction for the formation of carbon-carbon bonds in organic synthesis

Value in complex organic molecule construction and drug discovery

Due to its unique structure

Upstream product

• 40138-16-7 2-formylbenzene boronic acid 
• 593-56-6 N-methoxylamine hydrochloride 
• 67-62-9 O-Methylhydroxylamin 
• 380151-85-9 2-(2'-formylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 5941-05-9 salicylaldehyde acetylhydrazone 
• 67-62-9 O-Methylhydroxylamin 
• 40138-16-7 2-formylbenzene boronic acid 
• 17604-34-1 2-benzo[1,3,2]dioxaborol-2-yl-benzaldehyde O-methyl-oxime 

Relevant articles and documents

Boronic acids facilitate rapid oxime condensations at neutral pH

We report here the discovery and development of boron-assisted oxime formation as a powerful connective reaction for chemical biology. Oximes proximal to boronic acids form in neutral aqueous buffer with rate constants of more than 104 M-1

Tuning the exchange dynamics of boronic acid hydrazones and oximes with pH and redox control

Dynamic bonds continually form and dissociate at equilibrium. Carbonyl compounds with proximal boronic acids, including 2-formylphenylboronic acid (2-FPBA), have been reported to form highly dynamic covalent hydrazone and oxime bonds in physiological conditions, but strategies to tune the dynamics have not yet been reported. Here, we characterize the dynamics of 2-FPBA-derived hydrazones and oximes and account for both the rapid rate of formation (～102-103M?1s?1) and the relatively fast rate of hydrolysis (～10?4s?1) at physiological pH. We further show that these substrates undergo exchange with α-nucleophiles, which can be reversibly paused and restarted with pH control. Finally, we show that oxidation of the arylboronic acid effectively abolishes the rapid dynamics, which slows the forward reaction by more than 30?000 times and increases the hydrolytic half-life from 50 minutes to 6 months at physiological pH. These results set the stage to explore these linkages in dynamic combinatorial libraries, reversible bioconjugation, and self-healing materials.