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633348
Vinylboronic acid pinacol ester
contains phenothiazine as stabilizer, 95%
Synonim(y):
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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About This Item
Wzór empiryczny (zapis Hilla):
C8H15BO2
Numer CAS:
Masa cząsteczkowa:
154.01
Numer MDL:
Kod UNSPSC:
12352103
Identyfikator substancji w PubChem:
NACRES:
NA.22
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Próba
95%
zawiera
phenothiazine as stabilizer
współczynnik refrakcji
n20/D 1.4300 (lit.)
gęstość
0.908 g/mL at 25 °C (lit.)
temp. przechowywania
−20°C
ciąg SMILES
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
Klucz InChI
DPGSPRJLAZGUBQ-UHFFFAOYSA-N
Zastosowanie
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)
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Hasło ostrzegawcze
Warning
Zwroty wskazujące rodzaj zagrożenia
Zwroty wskazujące środki ostrożności
Klasyfikacja zagrożeń
Aquatic Chronic 2 - Flam. Liq. 3 - Skin Sens. 1
Kod klasy składowania
3 - Flammable liquids
Klasa zagrożenia wodnego (WGK)
WGK 3
Temperatura zapłonu (°F)
93.2 °F
Temperatura zapłonu (°C)
34 °C
Środki ochrony indywidualnej
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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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.
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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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