Vinylboronic acid MIDA ester
Product Information
Molecular Formula
C7H10BNO4
Molecular Weight
182.97
Description
• 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-couplingsSuzuki Cross-Coupling with MIDA Boronates
MIDA boronates as stable boronic acid surrogates for classically challenging cross-couplingsSuzuki Cross-Coupling with MIDA Boronates
Synonyms
6-Methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione
IUPAC Name
2-ethenyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
SMILES
B1(OC(=O)CN(CC(=O)O1)C)C=C
InChI
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
Melting Point
152-156 °C
Flash Point
Not applicable
Purity
97%
Storage
2-8°C
Computed Properties
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
1
Exact Mass
183.0702880 g/mol
Monoisotopic Mass
183.0702880 g/mol
Topological Polar Surface Area
55.8Ų
Heavy Atom Count
13
Formal Charge
0
Complexity
223
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| WO-2021009334-A2 | Herbicidal compounds | 2019-07-18 |
| WO-2021009335-A1 | Substituted pyridazinones as herbicides | 2019-07-18 |
| AU-2020313369-A1 | Substituted pyridazinones as herbicides | 2019-07-18 |
| AU-2020315159-A1 | Substituted pyridazinones as herbicides | 2019-07-18 |
| CA-3146243-A1 | Herbicidal compounds | 2019-07-18 |
| CA-3146246-A1 | Substituted pyridazinones as herbicides | 2019-07-18 |
| CN-114144409-A | Substituted pyridazinones as herbicides | 2019-07-18 |
| US-2020388885-A1 | Silicon-based energy storage devices with lipo2f2 salt-containing electrolyte formulations | 2019-06-05 |
| JP-2022514253-A | N- (Pyridine-2-ylsulfonyl) cyclopropanecarboxamide derivative and its use in the treatment of CFTR-mediated diseases | 2018-12-18 |
| US-2022033407-A1 | N-(pyridin-2-ylsulfonyl)cyclopropanecarboxamide Derivatives and their Use in the Treatment of Disease | 2018-12-18 |
