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637998

Sigma-Aldrich

Vinylboronic anhydride pyridine complex

95%

Synonym(s):

2,4,6-Trivinylcyclotriboroxane pyridine complex, Trivinyl-boroxin pyridine complex, Trivinylcyclotriboroxane pyridine complex

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About This Item

Empirical Formula (Hill Notation):
C6H9B3O3 · C5H5N
CAS Number:
442850-89-7
Molecular Weight:
240.67
MDL number:
MFCD03839940
UNSPSC Code:
12352103
PubChem Substance ID:
24882902
NACRES:
NA.22

Quality Level

100

Assay

95%

form

solid

storage temp.

−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

InChI key

YLHJACXHRQQNQR-UHFFFAOYSA-N

Application

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

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Precautionary Statements

P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

176.0 °F - closed cup

Flash Point(C)

80 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Kinetic resolution of phosphoryl and sulfonyl esters of 1,1'-bi-2-naphthol via Pd-catalyzed alcoholysis of their vinyl ethers
Sakuma, T.; et al.
Tetrahedron, 19, 1593-1599 (2008)
Intramolecular Heck reaction strategy for the synthesis of functionalized tetrahydroanthracenes: a facile formal total synthesis of the linear abietane diterpene, umbrosone
Sengupta, S.; et al.
Tetrahedron Letters, 46, 1515-1519 (2005)
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
Kuan-Jen Su et al.
The Journal of organic chemistry, 75(21), 7494-7497 (2010-10-14)
Tetravinylbenzene 4 was prepared in nearly quantitative yield from commercially available tetrabromobenzene; the improved, one-step procedure now employs Suzuki-Miyaura cross-coupling conditions. Intermolecular cyclopropanation of 4 with dibromocarbene gave a series of gem-dibromide adducts. Intramolecular cyclopropanation of monoadduct 5, putatively by
Amanda F Ward et al.
Organic letters, 13(17), 4728-4731 (2011-08-05)
The stereoselective synthesis of 2,4- and 2,5-disubstituted 1,3-oxazolidines is accomplished via Pd-catalyzed carboamination of O-vinyl-1,2-amino alcohol derivatives. The transformations generate cis-disubstituted products with good to excellent diastereoselectivity, and enantiomerically enriched substrates are converted without loss of optical purity. In addition
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