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637998

Sigma-Aldrich

Vinylboronic anhydride pyridine complex

95%

Sinonimo/i:

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

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105,00 €
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354,00 €

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1 G
105,00 €
5 G
354,00 €

About This Item

Formula empirica (notazione di Hill):
C6H9B3O3 · C5H5N
Numero CAS:
442850-89-7
Peso molecolare:
240.67
Numero MDL:
MFCD03839940
Codice UNSPSC:
12352103
ID PubChem:
24882902
NACRES:
NA.22

105,00 €

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Saggio

95%

Stato

solid

Temperatura di conservazione

−20°C

Stringa SMILE

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
YLHJACXHRQQNQR-UHFFFAOYSA-N

Categorie correlate

Applicazioni

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

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H319

Consigli di prudenza

P305 + P351 + P338

Classi di pericolo

Eye Irrit. 2

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

176.0 °F - closed cup

Punto d’infiammabilità (°C)

80 °C - closed cup

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
0000319336
0000290874
0000216636
0000216635
0000205293

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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
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)
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
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)
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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