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704415 Sigma-Aldrich

Vinylboronic acid MIDA ester

97%

Synonym: 6-Methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione

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Properties

Related Categories Alkenyl MIDA Boronates, Boronic Acids and Derivatives, Chemical Synthesis, MIDA Boronates, Organometallic Reagents More...
InChI Key   MGRQGYAVASCCAK-UHFFFAOYSA-N
assay   97%
mp   152-156 °C
storage temp.   2-8°C

Description

Packaging

1, 5, 25, 100 g in glass bottle

Application

• 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.

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

Suzuki Cross-Coupling with MIDA Boronates

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.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
2

Same Products - New Packaging
Protocols & Articles

Articles

MIDA Boronates for Suzuki–Miyaura Cross-Couplings

Professor Martin Burke and coworkers recently prepared retinal using key MIDA building block BB1 in iterative Suzuki-Miyaura cross coupling reactions (Scheme 1). The MIDA unit of BB1 is unreactive un...
Aaron Thornton
ChemFiles Volume 11 Article 1
Keywords: Building blocks, Coupling reactions, Cross couplings, Solvents

MIDA-protected Boronate Esters

The Suzuki-Miyaura cross-coupling reaction is one of the most important and highly utilized reactions in organic chemistry, with applications in polymer science as well as in the fine chemicals and p...
Josephine Nakhla
ChemFiles Volume 9 Article 1
Keywords: Aminations, Applications, Bromoborations, Building blocks, Catalysis, Chemfiles, Chromatography, Coupling reactions, Cross couplings, Cross metathesis, Cyclopropanations, Epoxidations, Industries, Ligands, Metathesis, Methods, Natural product synthesis, Olefin metathesis, Pharmaceutical, Polymer science, Protocols, Purification, Reductions, Reductive aminations, Stille coupling, Suzuki coupling, Suzuki reactions, Takai olefination, Transmetalation, Type, transformation

Preparation of trans-(2-bromovinyl) MIDA Boronate and Vinyl MIDA Boronate from the Corresponding Silanes

Due to the instability of some boronic acids, the Burke group has developed very practical syntheses of some of the more challenging MIDA boronates. For instance, while trans-(2-bromovinyl) MIDA boro...
Josephine Nakhla
ChemFiles Volume 9 Article 1
Keywords: Bromoborations, Building blocks, Transmetalation

Related Content

New MIDA Boronates from Aldrich

MIDA boronates are stable boronic acid surrogates used for Suzuki-Miyaura cross-coupling reactions. These reagents enable the coupling of historically unstable organoboron species; including those co...
Keywords: Aldrichimica Acta, Coupling reactions, Cross couplings, Nuclear magnetic resonance spectroscopy

Peer-Reviewed Papers
15

References

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