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324647 Aldrich

Allylboronic acid pinacol ester

97%

Synonym: 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 4,4,5,5-tetramethyl-2-(2-propen-1-yl)-1,3,2-dioxaborolane, 4,4,5,5-tetramethyl-2-(2-propenyl)-1,3,2-dioxaborolane, Allyl pinacol boronate, Pinacol allylboronate, Pinacolyl 2-propenylboronate

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Properties

Related Categories Alkyl Boronate Esters, Boronate Esters, Boronic Acids and Derivatives, Chemical Synthesis, Organometallic Reagents More...
InChI Key   YMHIEPNFCBNQQU-UHFFFAOYSA-N
assay   97%
refractive index   n20/D 1.4268(lit.)
bp   50-53 °C/5 mmHg(lit.)
density   0.896 g/mL at 25 °C(lit.)
storage temp.   2-8°C

Description

Packaging

1, 10 g in glass bottle

Application

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

Price and Availability


KitAlysis - Increasing Catalysis Productivity

Cross-Coupling Guide
Safety & Documentation

Safety Information

Symbol 
GHS02  GHS02
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
UN 1993C 3 / PGIII
WGK Germany 
3
Flash Point(F) 
114.8 °F
Flash Point(C) 
46 °C
Protocols & Articles

Articles

Boronic Acid Esters - Chemfiles Volume 4 Article 2

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available. Several years ago, Miyaura et al. demonst...
Chemfiles Volume 4 Article 2
Keywords: Coupling reactions

Ligand-Controlled Palladium-Catalyzed Regiodivergent Suzuki- Miyaura Cross-Coupling of Allylboronates and Aryl Halides-

Pd-PEPPSI-IPent has proven to be an excellent catalyst for the Negishi cross-coupling reaction of secondary alkylzinc reagents with a wide variety of aryl/heteroaryl halides. Importantly, b-hydride e...
Keywords: Chromatography, Coupling reactions, Cross couplings, Eliminations, Flash chromatography, Ligands, Nuclear magnetic resonance spectroscopy, Purification

Peer-Reviewed Papers
15

References

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