(6-methoxynaphthalen-2-yl)boronic acid

• ChemBase ID: 32909
• Molecular Formular: C11H11BO3
• Molecular Mass: 202.01424
• Monoisotopic Mass: 202.08012461
• SMILES: c1c(ccc2cc(ccc12)OC)B(O)O
• Canonical SMILES: COc1ccc2c(c1)ccc(c2)B(O)O
• InChI: InChI=1S/C11H11BO3/c1-15-11-5-3-8-6-10(12(13)14)4-2-9(8)7-11/h2-7,13-14H,1H3
• InChIKey: GZFAVYWCPSMLCM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6-methoxynaphthalen-2-yl)boronic acid
• IUPAC Traditional name: 6-methoxynaphthalen-2-ylboronic acid
• Synonyms: 6-Methoxy-2-naphthalenylboronic acid; 6-Methoxy-2-naphthylboronic acid; 6-Methoxynaphthalene-2-boronic acid; 6-Methoxy-2-naphthaleneboronic acid; 6-Methoxynaphthalene-2-boronic acid; (6-methoxy-2-naphthyl)boronic acid; 6-Methoxynaphthalene-2-boronic acid; 6-Methoxy-2-naphthaleneboronic acid; 6-甲氧基-2-萘硼酸

Database IDs

• CAS Number: 156641-98-4
• MDL Number: MFCD03093087
• Beilstein Number: 7636998
• PubChem SID: 160996216; 24874233
• PubChem CID: 4641692

CALCULATED PROPERTIES

• Acid pKa: 8.706526
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.3890316
• LogD (pH = 7.4): 2.3684824
• Log P: 2.3893
• Molar Refractivity: 53.5169 cm^3
• Polarizability: 23.580858 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >295 °C(lit.); >295°C; ca 245°C dec.

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95%; 95%; 97%
• Linear Formula: C10H6OCH3B(OH)2

DETAILS

Sigma Aldrich - 521892

General description
Contains varying amounts of anhydride.
Packaging
5 g in glass bottle
Application
Reactant for:
• Suzuki-Miyaura coupling1
• Enantioselective a-arylation of carbonyls via copper-bisoxazoline catalysis2
• Enantioselective synthesis of aryl ketones3
• Copper-catalyzed trifluoromethylation4
• Rhodium-catalyzed oxidative coupling with alkynes5