1072960-66-7

Basic information

• Product Name: 4-formylphenylboronic acid
• Synonyms: 4-formylphenylboronic acid
• CAS NO: 1072960-66-7
• Molecular Weight: 261.042
• Mol File: 1072960-66-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4-formylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-formylphenylboronic acid(1072960-66-7)
• EPA Substance Registry System: 4-formylphenylboronic acid(1072960-66-7)

Safety Data

• Hazardous Substances Data: 1072960-66-7(Hazardous Substances Data)

Upstream product

• 4408-64-4 N-methyliminodiacetic acid 
• 87199-17-5 4-formylphenylboronic acid, 
• 13480-36-9 (N-methylimino)diacetic acid anhydride 
• 1072960-82-7 4-(hydroxymethyl)phenylboronic acid MIDA ester 

Downstream Products

• 1072960-75-8 (OC₄H₈NCH₂C₆H₄)BN(CH₃)(CH₂CO₂)2 
• 1072960-82-7 4-(hydroxymethyl)phenylboronic acid MIDA ester 
• 1072960-73-6 (ICHCHC₆H₄)BN(CH₃)(CH₂CO₂)2 
• 1072960-72-5 (C₂H₅OCOCHCHC₆H₄)BN(CH₃)(CH₂CO₂)2 
• 952514-79-3 (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid 
• 1259883-01-6 N,N-diphenyl-4'-(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1'-biphenyl]-4-amine 

Relevant articles and documents

A Mild Method for Making MIDA Boronates

We disclose that a predried form of methyliminodiacetic acid (MIDA), MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in laboratories that do not specialize in organic synthesis.

Synthesis of Benzimidazole-Substituted Arylboronic Acids via Aerobic Oxidation of 1,2-Arylenediamines and Formyl-Substituted Aryl MIDA Boronates using Potassium Iodide as a Catalyst

A highly efficient protocol for the synthesis of benzimidazole-substituted arylboronic acids was developed via aerobic oxidative cyclization of 1,2-aryldiamines and formyl-substituted aryl MIDA (N-methyliminodiacetic acid) boronates using potassium iodide as a nucleophilic catalyst. Furthermore, a one-pot protocol for the synthesis of benzimidazole-substituted arylboronic acids from 1,2-phenylenediamines and formyl-substituted arylboronic acids was developed without the isolation of any intermediates. The resulting boronic acids were further subjected to Suzuki-Miyaura coupling reactions without isolation, leading to diaryl-substituted benzimidazoles with only one separation step.

Multistep synthesis of complex boronic acids from simple MIDA boronates

Due to its sensitivity to most synthetic reagents, it is typically necessary to introduce the boronic acid functional group just prior to its utilization. Overcoming this important limitation, we herein report that air- and chromatographically stable MIDA boronates are compatible with a wide range of common reagents which enables the multistep synthesis of complex boronic acid building blocks from simple B-containing starting materials. X-ray and variable temperature NMR studies link the unique stability of MIDA boronates to a kinetic inaccessibility of the potentially reactive boron p-orbital and/or nitrogen lone pair. These findings were collectively harnessed to achieve a short and modular total synthesis of (+)-crocacin C via the iterative cross-coupling of a structurally complex, MIDA-protected haloboronic acid building block. Copyright