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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:
Molekulargewicht:
168.04
MDL-Nummer:
UNSPSC-Code:
12352103
PubChem Substanz-ID:
NACRES:
NA.22
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Qualitätsniveau
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
Verwandte Kategorien
Allgemeine Beschreibung
Allylboronic acid pinacol ester is used as a nucleophile in the catalytic allylation of simple ketoimines.
Anwendung
Reagent used for
Reagent used in Preparation of
- 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.
Signalwort
Warning
H-Sätze
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
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Gaining absolute control of the regiochemistry in the cobalt-catalyzed 1,4-hydrovinylation reaction.
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
Organometallics, 2, 230-230 (1983)
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)
Manuel Röthlingshöfer et al.
Journal of the American Chemical Society, 133(45), 18110-18113 (2011-10-19)
The photocleavage of a nitrobenzyl-type linker (NPPOC) at 405 nm wavelength was enabled by nucleic acid-templated energy transfer from a sensitizer (thioxanthenone) to the linker. This strategy was used to release profluorescent rhodamine, which facilitated monitoring of the reaction via
Catalytic enantioselective allylation of ketoimines
Reiko W et al.
Journal of the American Chemical Society, 128, 7687-7691 (2006)
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