cyclopropylboronic acid

• ChemBase ID: 32911
• Molecular Formular: C3H7BO2
• Molecular Mass: 85.89748
• Monoisotopic Mass: 86.05390986
• SMILES: C1(CC1)B(O)O
• Canonical SMILES: OB(C1CC1)O
• InChI: InChI=1S/C3H7BO2/c5-4(6)3-1-2-3/h3,5-6H,1-2H2
• InChIKey: WLVKDFJTYKELLQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: cyclopropylboronic acid
• IUPAC Traditional name: cyclopropylboronic acid
• Synonyms: Cyclopropyl boronic acid; B-Cyclopropylboronic Acid; Boronocyclopropane; Cyclopropylboronic acid 95%; Cyclopropylboronic acid; Cyclopropaneboronic acid; Cyclopropylboronic acid; 环丙基硼酸

Database IDs

• CAS Number: 411235-57-9
• MDL Number: MFCD04038750
• PubChem SID: 160996218; 24881728
• PubChem CID: 2760897

CALCULATED PROPERTIES

• Acid pKa: 8.808934
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.568688
• LogD (pH = 7.4): 0.5523766
• Log P: 0.5689
• Molar Refractivity: 17.8121 cm^3
• Polarizability: 8.764483 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 90-95 °C(lit.); 90-95°C; 90-95°C; 94-97°C

Safety Information

• Storage Warning: Harmful/Irritant/Store under Argon/Store at -20°C; IRRITANT, IRRITANT-HARMFUL
• European Hazard Symbols: Toxic (T); Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 60-61-22-36
• Safety Statements: 26-37; 53-26-45
• TSCA Listed: false; 否
• GHS Pictograms: GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H318-H360FD; H315-H319-H335
• GHS Precautionary statements: P201-P280-P305 + P351 + P338-P308 + P313; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Storage Temperature: -20°C

Product Information

• Purity: 90%; 95+%; 97%; 98%; tech. 85%
• Empirical Formula (Hill Notation): C3H7BO2

DETAILS

Sigma Aldrich - 597988

Frequently Asked Questions
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Other Notes
Contains varying amounts of anhydride
May contain 3-5% cyclopropanol
May contain 5-10% boric acid
Packaging
1, 5, 25 g in glass bottle
Application
Reagent used for
• Microwave-assisted copper(II)-catalyzed N-cyclopropylation1
• Nickel- and copper-catalyzed Suzuki-Miyaura coupling reaction of arenes2
• Palladacycle-catalyzed Suzuki-cross coupling of aryl halides with cyclopropylboronic acid3
• Palladium(0)-catalyzed cyclopropane C-H bond functionalization4
• Palladium-catalyzed decarboxylative coupling5
• Palladium-catalyzed ligand-directed oxidative functionalization of cyclopropanes6
• Palladium-catalyzed Suzuki coupling reaction7Reagent used in Preparation of
• Diaryl ketones by arylation of arylboronic acids with aromatic aldehydes catalyzed by Cu(OTf)2 and Xantphos8
• Aminothiazolylpyrrolidine-based tartrate diamides as TACE inhibitors to treat inflammatory disorders and cancer9

Toronto Research Chemicals - C988620

Cyclopropylboronic Acid is an organoboronic acid commonly used in highly efficient Suzuki coupling reactions.

REFERENCES

• Ma, S. et al.: Adv. Synth. Cat., 348, 2114 (2006)