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Merck

637998

Sigma-Aldrich

Vinylboronsäureanhydrid-Pyridin-Komplex

95%

Synonym(e):

2,4,6-Trivinylcyclotriboroxan-pyridin-Komplex

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95,20 €
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354,00 €

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Versandbereit am14. April 2025Details


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1 G
95,20 €
5 G
354,00 €

About This Item

Empirische Formel (Hill-System):
C6H9B3O3 · C5H5N
CAS-Nummer:
Molekulargewicht:
240.67
MDL-Nummer:
UNSPSC-Code:
12352103
PubChem Substanz-ID:
NACRES:
NA.22

95,20 €


Versandbereit am14. April 2025Details


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Qualitätsniveau

Assay

95%

Form

solid

Lagertemp.

−20°C

SMILES String

c1ccncc1.C=Cb2ob(C=C)ob(C=C)o2

InChI

1S/C6H9B3O3.C5H5N/c1-4-7-10-8(5-2)12-9(6-3)11-7;1-2-4-6-5-3-1/h4-6H,1-3H2;1-5H

InChIKey

YLHJACXHRQQNQR-UHFFFAOYSA-N

Anwendung

Reagent used for
  • Suzuki-Miyaura cross-coupling[1][2]
  • Stereoselective synthesis via Palladium-catalyzed carboamination[3]
  • Alkyl-connected 2-amino-6-vinylpurine (AVP) crosslinking agent to cytosine base in RNA[4]
  • Kaiser oxime resin-derived palladacycle as a recoverable polymeric precatalyst in Suzuki-Miyaura cross-coupling reactions in aqueous media[5]
  • Kinetic resolution of phosphoryl and sulfonyl esters of binaphthol derivatives via Pd-catalyzed alcoholysis of their vinyl ethers[6]
  • Stereoselective isomerization of N-allyl aziridines into Z-enamines by using rhodium hydride catalysis[7]
  • Kinetic resolution of axially chiral biaryl derivatives via palladium/chiral diamine ligand-catalyzed alcoholysis[8]
  • Transition metal-catalyzed alkenylation of aziridines, cycloaddition and thermal rearrangement reactions[9]
  • Intramolecular Heck reaction strategy for synthesis of functionalized tetrahydroanthracenes[10]

Reagent used for Preparation of
  • BACE-1 inhibitors and SAR of cyclic sulfone hydroxyethylamines[11]
  • Distorted spiropentanes[1]
  • Small molecule bradykinin B2 receptor antagonists in angioedema therapy[12]
  • Enol Ethers[13]
  • Styryl cyclobutanone

Piktogramme

Exclamation mark

Signalwort

Warning

H-Sätze

Gefahreneinstufungen

Eye Irrit. 2

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

176.0 °F - closed cup

Flammpunkt (°C)

80 °C - closed cup

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


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Die Dokumentenbibliothek aufrufen

Hiroshi Aoyama et al.
Journal of the American Chemical Society, 127(30), 10474-10475 (2005-07-28)
Palladium-diamine complexes catalyzed kinetic resolution of axially chiral 2,2'-dihydroxy-1,1'-biaryls by alcoholysis of vinyl ethers. The reaction proceeded with high selectivity for various kinds of biaryls. This process is applicable to not only binaphthols but also biphenols, which have been considered
Shadi Dalili et al.
Organic letters, 7(6), 1161-1164 (2005-03-12)
[reaction: see text] Straightforward methods for palladium-catalyzed alkenylation of aziridines with alkenyl halides and copper-catalyzed alkenylation of aziridines with alkenyl boronic acids have been developed. This methodology offers attractive alternatives to the known methods requiring activated alkenyl halides and acetylenes.
Kaiser oxime resin-derived palladacycle: A recoverable polymeric precatalyst in Suzuki-Miyaura reactions in aqueous media
Alacid, E.; Najera, C.
Journal of Organometallic Chemistry, 694, 1658-1665 (2009)
Heinrich Rueeger et al.
Bioorganic & medicinal chemistry letters, 21(7), 1942-1947 (2011-03-11)
This Letter describes the de novo design of non-peptidic hydroxyethylamine (HEA) inhibitors of BACE-1 by elimination of P-gp contributing amide attachments. The predicted binding mode of the novel cyclic sulfone HEA core template was confirmed in a X-ray co-crystal structure.
Yosuke Taniguchi et al.
Bioorganic & medicinal chemistry, 18(8), 2894-2901 (2010-03-30)
We have previously reported that the 2-amino-6-vinylpurine (AVP) nucleoside exhibits a highly efficient and selective crosslinking reaction toward cytosine and displayed an improved antisense inhibition in cultured cells. In this study, we further investigated the alkyl-connected AVP nucleoside analogs for

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