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633348

Sigma-Aldrich

Vinylboronsäurepinakolester

contains phenothiazine as stabilizer, 95%

Synonym(e):

4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolan

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About This Item

Empirische Formel (Hill-System):
C8H15BO2
CAS-Nummer:
75927-49-0
Molekulargewicht:
154.01
MDL-Nummer:
MFCD00192492
UNSPSC-Code:
12352103
PubChem Substanz-ID:
24882546
NACRES:
NA.22

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Qualitätsniveau

100

Assay

95%

Enthält

phenothiazine as stabilizer

Brechungsindex

n20/D 1.4300 (lit.)

Dichte

0.908 g/mL at 25 °C (lit.)

Lagertemp.

−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

InChIKey

DPGSPRJLAZGUBQ-UHFFFAOYSA-N

Verwandte Kategorien

Anwendung

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.[1] Also used to prepare γ-carbonyl vinyl boronates via a light-induced radical addition of xanthates.[2]
Reagent used for
  • Suzuki-Miyaura coupling reactions[3]
  • Mizoroki-Heck reactions (cascade reaction)[3]
  • Intramolecular Nozaki-Hiyama-Kishi reactions[4]
  • Stereoselective Cu-catalyzed γ-selective and stereospecific coupling[5]
  • Control of stereoselectivity and mechanistic portrait on intramolecular (4+1)-cycloaddition of dialkoxycarbenes[6]
  • Regio- and stereoselective synthesis of trisubstituted alkenes via gold(I)-catalyzed hydrophosphoryloxylation of haloalkynes followed by Pd-catalyzed consecutive cross-coupling reactions[7]
  • Asymmetric Birch reductive alkylation[8]

Reagent used in Preparation of
  • Molecular tubes for lipid sensing[9]
  • Enzymatic inhibitors, antibiotics, receptor analogs, and other biologically significant compounds (including total syntheses)[10][11][12][4]

Signalwort

Warning

Gefahreneinstufungen

Aquatic Chronic 2 - Flam. Liq. 3 - Skin Sens. 1

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 3

Flammpunkt (°F)

93.2 °F

Flammpunkt (°C)

34 °C

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
MKCW2120
0000202873
0000201611
0000202873
0000201611

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4-Vinylphenylborsäure ≥95%

Sigma-Aldrich

417580

4-Vinylphenylborsäure

Tributyl(vinyl)zinn 97%

Sigma-Aldrich

271438

Tributyl(vinyl)zinn

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.
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.
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
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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