704415

Vinylboronic acid MIDA ester

97%

• Synonym(s): 6-Methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione
• Empirical Formula (Hill Notation): C₇H₁₀BNO₄
• CAS Number: 1104636-73-8
• Molecular Weight: 182.97
• MDL number: MFCD11656092
• UNSPSC Code: 12352103
• PubChem Substance ID: 329762451
• NACRES: NA.22

Properties

• assay: 97%
• form: powder
• mp: 152-156 °C
• storage temp.: 2-8°C
• SMILES string: CN1CC(=O)OB(OC(=O)C1)C=C
• InChI: 1S/C7H10BNO4/c1-3-8-12-6(10)4-9(2)5-7(11)13-8/h3H,1,4-5H2,2H3
• InChI key: MGRQGYAVASCCAK-UHFFFAOYSA-N

Description

General description

Vinylboronic acid MIDA ester, like other MIDA boronates, possesses the capacity for controlled, in situ slow-release of boronic acids under aqueous basic conditions allowing the cross-coupling of classically challenging substrates.

Application

MIDA boronates as stable boronic acid surrogates for classically challenging cross-couplings

Suzuki Cross-Coupling with MIDA Boronates

• Vinylboronic acid MIDA ester is an air and chromatographically stable boronic acid surrogate for Suzuki-Miyaura cross-coupling. It can also be used in Heck and oxidative Heck reactions as well as in olefin metathesis to provide the cross-coupled product.
• It is compatible with a wide range of common synthetic reagents that allows functionalization to synthesize structurally complex boronic acid surrogates.
• It undergoes cyclopropanation and epoxidation to yield corresponding MIDA cyclopropane and oxirane, respectively.
• It can be used as one of the major reagents for the scalable synthesis of potent cytotoxin, Leiodermatolide and for the total synthesis of (−)-Blepharocalyxin D.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)