(2-methoxynaphthalen-1-yl)boronic acid

• ChemBase ID: 143279
• Molecular Formular: C11H11BO3
• Molecular Mass: 202.01424
• Monoisotopic Mass: 202.08012461
• SMILES: B(c1c2ccccc2ccc1OC)(O)O
• Canonical SMILES: COc1ccc2c(c1B(O)O)cccc2
• InChI: InChI=1S/C11H11BO3/c1-15-10-7-6-8-4-2-3-5-9(8)11(10)12(13)14/h2-7,13-14H,1H3
• InChIKey: NHVWTZOWDLOBBS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-methoxynaphthalen-1-yl)boronic acid
• IUPAC Traditional name: 2-methoxynaphthalen-1-ylboronic acid
• Synonyms: (2-Methoxy-1-naphthalenyl)boronic acid; (2-Methoxy-1-naphthyl)boronic acid; 1-(2-Methoxynaphthyl)boronic acid; 2-Methoxy-1-naphthaleneboronic acid; 2-甲氧基-1-萘硼酸

Database IDs

• CAS Number: 104116-17-8
• MDL Number: MFCD11044173
• PubChem SID: 162237500
• PubChem CID: 4198751

CALCULATED PROPERTIES

• Acid pKa: 8.277912
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.3885803
• LogD (pH = 7.4): 2.3355422
• Log P: 2.3893
• Molar Refractivity: 53.5169 cm^3
• Polarizability: 23.584383 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 125-130 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338

Product Information

• Empirical Formula (Hill Notation): C11H11BO3

DETAILS

Sigma Aldrich - 717657

Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Design of phosphorus C,P-ligands for environmentally benign cross-coupling reactions1
• Sterically hindered Suzuki-Miyaura coupling2
• Palladium-catalyzed cross-coupling reactions3
• Deboronation homocoupling reactions4
• Copper-catalyzed N-arylation of imidazoles5
• Stereoselective preparation of biaryl compounds via palladium-catalyzed asymmetric Suzuki-Miyaura coupling6