633348
Vinylboronic acid pinacol ester
contains phenothiazine as stabilizer, 95%
Synonym(s):
2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-Vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaoborolane, 4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolane
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All Photos(4)
About This Item
Empirical Formula (Hill Notation):
C8H15BO2
CAS Number:
Molecular Weight:
154.01
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
95%
contains
phenothiazine as stabilizer
refractive index
n20/D 1.4300 (lit.)
density
0.908 g/mL at 25 °C (lit.)
storage temp.
−20°C
SMILES string
CC1(C)OB(OC1(C)C)C=C
InChI
1S/C8H15BO2/c1-6-9-10-7(2,3)8(4,5)11-9/h6H,1H2,2-5H3
InChI key
DPGSPRJLAZGUBQ-UHFFFAOYSA-N
Related Categories
Application
Employed in a "double" Heck-Mizoroki arylation leading to β,β-diarylated vinyl boronates which react with an additional aryl halide to form Π-extended systems. This approach was used to prepare conjugated dendrimers. Also used to prepare γ-carbonyl vinyl boronates via a light-induced radical addition of xanthates.
Reagent used for
Reagent used in Preparation of
- Suzuki-Miyaura coupling reactions
- Mizoroki-Heck reactions (cascade reaction)
- Intramolecular Nozaki-Hiyama-Kishi reactions
- Stereoselective Cu-catalyzed γ-selective and stereospecific coupling
- Control of stereoselectivity and mechanistic portrait on intramolecular (4+1)-cycloaddition of dialkoxycarbenes
- Regio- and stereoselective synthesis of trisubstituted alkenes via gold(I)-catalyzed hydrophosphoryloxylation of haloalkynes followed by Pd-catalyzed consecutive cross-coupling reactions
- Asymmetric Birch reductive alkylation
Reagent used in Preparation of
- Molecular tubes for lipid sensing
- Enzymatic inhibitors, antibiotics, receptor analogs, and other biologically significant compounds (including total syntheses)
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Chronic 2 - Flam. Liq. 3 - Skin Sens. 1
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
93.2 °F
Flash Point(C)
34 °C
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Customers Also Viewed
Markus R Heinrich et al.
Chemical communications (Cambridge, England), (24), 3077-3079 (2005-06-17)
Gamma-carbonyl vinyl boronates can be prepared by a visible light induced radical chain addition of an S-acyl dithiocarbonate (xanthate) to the pinacol ester of vinyl boronic acid, followed by treatment with base.
Mingyu Yang et al.
Organic letters, 14(3), 816-819 (2012-01-20)
A Cu-catalyzed γ-selective coupling reaction between propargylic phosphates and aryl- or alkenylboronates afforded aryl- or alkenyl-conjugated allenes. The reaction showed excellent functional group compatibility in both the propargylic substrates and the boronates. The reaction of an enantioenriched propargylic phosphate proceeded
Francis Beaumier et al.
Journal of the American Chemical Society, 134(13), 5938-5953 (2012-03-13)
The stereoselective synthesis of 5-5, 6-5, and 7-5 fused O-heterocyclic compounds is reported. The key reaction is a formal intramolecular (4 + 1)-cycloaddition involving a dialkoxycarbene and an electron-deficient diene where the stereoselectivity is dependent on the length of the
Bathoju Chandra Chary et al.
Chemical communications (Cambridge, England), 47(27), 7851-7853 (2011-06-07)
A new stereoselective synthesis of trisubstituted alkenes is developed. Hydrophosphoryloxylation of haloalkynes provides Z-alkenyl halophosphates, which undergo Pd-catalyzed consecutive cross-coupling reactions to afford regio- and stereodefined trisubstituted alkenes.
Christopher A Leclair et al.
Tetrahedron letters, 51(52), 6852-6855 (2011-04-26)
A total synthesis of LL-Z1640-2 (2), a potent and selective kinase inhibitor, has been completed. The key step of the convergent synthesis utilized a late-stage intramolecular Nozaki-Hiyama-Kishi (NHK) reaction to close the macrocycle at the C6'-C7' bond.
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