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633348

Sigma-Aldrich

Vinylboronic acid pinacol ester

contains phenothiazine as stabilizer, 95%

Sinonimo/i:

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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69,70 €
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355,00 €

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1 G
69,70 €
10 G
355,00 €

About This Item

Formula empirica (notazione di Hill):
C8H15BO2
Numero CAS:
75927-49-0
Peso molecolare:
154.01
Numero MDL:
MFCD00192492
Codice UNSPSC:
12352103
ID PubChem:
24882546
NACRES:
NA.22

69,70 €

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Livello qualitativo

100

Saggio

95%

contiene

phenothiazine as stabilizer

Indice di rifrazione

n20/D 1.4300 (lit.)

Densità

0.908 g/mL at 25 °C (lit.)

Temperatura di conservazione

−20°C

Stringa SMILE

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
DPGSPRJLAZGUBQ-UHFFFAOYSA-N

Categorie correlate

Applicazioni

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]

Avvertenze

Warning

Indicazioni di pericolo

H226,H317,H411

Classi di pericolo

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

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

93.2 °F

Punto d’infiammabilità (°C)

34 °C

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
MKCW2120
0000202873
0000201611
MKCP9314
SHBJ8428

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Sigma-Aldrich

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Organic & biomolecular chemistry, 9(23), 8112-8118 (2011-10-26)
Simple models of the spiroimine core of (-)-gymnodimine A have been synthesized in racemic and optically active forms. The quaternary carbon of the racemic spiroimines was created by Michael addition of a β-ketoester to acrolein, whereas the asymmetric allylic alkylation
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Several 3-alkylaryl mimics of the enol intermediate in the reaction catalyzed by type II dehydroquinase were synthesized to investigate the effect on the inhibition potency of replacing the oxygen atom in the side chain by a carbon atom. The length
Total Synthesis and Biological Evaluation of the Fab-Inhibitory Antibiotic Platencin and Analogues Thereof
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The Journal of organic chemistry, 77(2), 851-857 (2012-01-24)
Two fluorescent sensors for lipids have been prepared and tested for detection of a number of hydrophobic compounds of varying shape and size. The data suggest that the two sensors have a different mode of fluorescent response. Yet, the two
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 risposta

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

    1 risposta

    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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