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704415

Sigma-Aldrich

Vinylboronic acid MIDA ester

97%

Synonym(s):

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

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About This Item

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

Quality Level

100

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

Related Categories

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP2460
SHBL0979
SHBK3494
SHBH2828V
SHBG6869V

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Synthesis of trans-2-(Trifluoromethyl) cyclopropanes via Suzuki reactions with an N-methyliminodiacetic acid boronate.
Duncton MA and Singh R.
Organic Letters, 15(17), 4284-4287 (2013)
(1-Bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis.
Woerly EM, et al.
Tetrahedron, 69(36), 7732-7740 (2013)
A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates.
Knapp DM, et al.
Journal of the American Chemical Society, 131(20), 6961-6963 (2009)
Total Synthesis of (−)-Blepharocalyxin D and Analogues.
Cons BD, et al.
Organic Letters, 15(8), 2046-2049 (2013)
Synthesis, molecular editing, and biological assessment of the potent cytotoxin leiodermatolide.
Mailhol D, et al.
Journal of the American Chemical Society, 136(44), 15719-15729 (2014)
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