704415

Vinylboronic acid MIDA ester

97%

• Synonyme(s) : 6-Methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione
• Formule empirique (notation de Hill): C₇H₁₀BNO₄
• Numéro CAS: 1104636-73-8
• Poids moléculaire : 182.97
• Numéro MDL: MFCD11656092
• Code UNSPSC : 12352103
• ID de substance PubChem : 329762451
• Nomenclature NACRES : NA.22

Propriétés

• Niveau de qualité: 100
• Pureté: 97%
• Forme: powder
• Pf: 152-156 °C
• Température de stockage: 2-8°C
• Chaîne SMILES: 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
• Clé InChI: MGRQGYAVASCCAK-UHFFFAOYSA-N

Description

Description générale

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.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 2
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)