324647

Allylboronic acid pinacol ester

97%

• Synonym(s): 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
• Linear Formula: ((CH₃)₄C₂O₂)BCH₂CH=CH₂
• CAS Number: 72824-04-5
• Molecular Weight: 168.04
• MDL number: MFCD00013347
• UNSPSC Code: 12352103
• PubChem Substance ID: 24859457
• NACRES: NA.22

Properties

• Quality Level: 100
• 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
• 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
• InChI key: YMHIEPNFCBNQQU-UHFFFAOYSA-N

Description

General description

Allylboronic acid pinacol ester is used as a nucleophile in the catalytic allylation of simple ketoimines. [1]

Application

Reagent used for

• Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions and olefin metathesis[2]
• Intermolecular radical additions[3]
• Allylboration of aldehydes catalyzed by chiral spirobiindane diol (SPINOL) based phosphoric acids[4]
• Cobalt-catalyzed regioselective hydrovinylation of dienes with alkenes[5]
• Nucleic acid-templated energy transfer leading to a photorelease reaction[6]
• Stereoselective indium-catalyzed Hosomi-Sakurai reactions[7]

Reagent used in Preparation of

• Cyclic sulfone hydroxyethylamines as BACE1 inhibitors for reduction of Amyloid β-Peptides[8]
• Transmetalation of carbene Ru iodide with Ag carboxylates to give C-H-activated Ru carbene complexes as catalysts for Z-selective olefin metathesis[9]
• Allylboronation reagent for the preparation of allylic alcohols[10], and homoallylic amines.[11]

Safety Information

• Pictograms: GHS02
• Signal Word: Warning
• Hazard Statements: H226
• Precautionary Statements: P210 - P233 - P240 - P241 - P242 - P243
• Hazard Classifications: Flam. Liq. 3
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): 114.8 °F - closed cup
• Flash Point(C): 46 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves