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Sigma-Aldrich

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolan

97%

Synonym(e):

Pinacol-allylboronat

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About This Item

Lineare Formel:
((CH3)4C2O2)BCH2CH=CH2
CAS-Nummer:
72824-04-5
Molekulargewicht:
168.04
MDL-Nummer:
MFCD00013347
UNSPSC-Code:
12352103
PubChem Substanz-ID:
24859457
NACRES:
NA.22

Assay

97%

Brechungsindex

n20/D 1.4268 (lit.)

bp

50-53 °C/5 mmHg (lit.)

Dichte

0.896 g/mL at 25 °C (lit.)

Lagertemp.

2-8°C

SMILES String

CC1(C)OB(CC=C)OC1(C)C

InChI

1S/C9H17BO2/c1-6-7-10-11-8(2,3)9(4,5)12-10/h6H,1,7H2,2-5H3

InChIKey

YMHIEPNFCBNQQU-UHFFFAOYSA-N

Allgemeine Beschreibung

Allylboronic acid pinacol ester is used as a nucleophile in the catalytic allylation of simple ketoimines.

Anwendung

Reagent used for
  • Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions and olefin metathesis
  • Intermolecular radical additions
  • Allylboration of aldehydes catalyzed by chiral spirobiindane diol (SPINOL) based phosphoric acids
  • Cobalt-catalyzed regioselective hydrovinylation of dienes with alkenes
  • Nucleic acid-templated energy transfer leading to a photorelease reaction
  • Stereoselective indium-catalyzed Hosomi-Sakurai reactions

Reagent used in Preparation of
  • Cyclic sulfone hydroxyethylamines as BACE1 inhibitors for reduction of Amyloid β-Peptides
  • Transmetalation of carbene Ru iodide with Ag carboxylates to give C-H-activated Ru carbene complexes as catalysts for Z-selective olefin metathesis
  • Allylboronation reagent for the preparation of allylic alcohols, and homoallylic amines.

Piktogramme

Flame
GHS02

Signalwort

Warning

H-Sätze

H226

Gefahreneinstufungen

Flam. Liq. 3

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 3

Flammpunkt (°F)

114.8 °F - closed cup

Flammpunkt (°C)

46 °C - closed cup

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

Nicolas Charrier et al.
Organic letters, 14(8), 2018-2021 (2012-04-03)
Adducts from the intermolecular radical addition of N-xanthylacetyl-N-methanesulfanilides to Boc-protected allylamine undergo ring closure with loss of a methanesulfonyl radical to give benzazepin-2-ones. Upon deprotection and exposure to triethylamine, these compounds rearrange into 5-aryl-2-piperidones. This approach also represents a useful
Heinrich Rueeger et al.
Journal of medicinal chemistry, 55(7), 3364-3386 (2012-03-03)
Structure-based design of a series of cyclic hydroxyethylamine BACE1 inhibitors allowed the rational incorporation of prime- and nonprime-side fragments to a central core template without any amide functionality. The core scaffold selection and the structure-activity relationship development were supported by
Marion Arndt et al.
Organic letters, 13(23), 6236-6239 (2011-11-02)
The absolute control of the regiochemistry of a cobalt-catalyzed 1,4-hydrovinylation reaction is achieved by alternation of the ligands applied. While the dppe/dppp ligands led to the formation of the branched product, the herein described application of the SchmalzPhos ligand generates
Asymmetric Allylboration of Aldehydes with Pinacol Allylboronates Catalyzed by 1,1'-Spirobiindane-7,7'-diol (SPINOL) Based Phosphoric Acids
Xing, C-H.; et al.
European Journal of Organic Chemistry, 6, 1115-1118 (2012)
Organometallics, 2, 230-230 (1983)
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