597988

Cyclopropylboronic acid

• Synonym(s): Cyclopropaneboronic acid
• Empirical Formula (Hill Notation): C₃H₇BO₂
• CAS Number: 411235-57-9
• Molecular Weight: 85.90
• MDL number: MFCD04038750
• UNSPSC Code: 12352103
• PubChem Substance ID: 24881728
• NACRES: NA.22

Properties

• form: solid
• mp: 90-95 °C (lit.)
• storage temp.: −20°C
• SMILES string: OB(O)C1CC1
• InChI: 1S/C3H7BO2/c5-4(6)3-1-2-3/h3,5-6H,1-2H2
• InChI key: WLVKDFJTYKELLQ-UHFFFAOYSA-N

Description

Application

Boronic acid component in a study of carbon-hydrogen bond alkylation in the presence of Pd(II), Ag(I) and benzoquinone.

Cu-mediated N-cyclopropanation

Reagent used for

• Microwave-assisted copper(II)-catalyzed N-cyclopropylation
• Nickel- and copper-catalyzed Suzuki-Miyaura coupling reaction of arenes
• Palladacycle-catalyzed Suzuki-cross coupling of aryl halides with cyclopropylboronic acid
• Palladium(0)-catalyzed cyclopropane C-H bond functionalization
• Palladium-catalyzed decarboxylative coupling
• Palladium-catalyzed ligand-directed oxidative functionalization of cyclopropanes
• Palladium-catalyzed Suzuki coupling reaction

Reagent used in Preparation of

• Diaryl ketones by arylation of arylboronic acids with aromatic aldehydes catalyzed by Cu(OTf)₂ and Xantphos
• Aminothiazolylpyrrolidine-based tartrate diamides as TACE inhibitors to treat inflammatory disorders and cancer

Other Notes

Contains varying amounts of anhydride

May contain 3-5% cyclopropanol

May contain 5-10% boric acid

Safety Information

• Pictograms: GHS08
• Signal Word: Danger
• Hazard Statements: H360FD
• Precautionary Statements: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Repr. 1B
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable