(naphthalen-2-yl)boronic acid

• ChemBase ID: 10046
• Molecular Formular: C10H9BO2
• Molecular Mass: 171.98826
• Monoisotopic Mass: 172.06955993
• SMILES: c1ccc2c(c1)ccc(c2)B(O)O
• Canonical SMILES: OB(c1ccc2c(c1)cccc2)O
• InChI: InChI=1S/C10H9BO2/c12-11(13)10-6-5-8-3-1-2-4-9(8)7-10/h1-7,12-13H
• InChIKey: KPTRDYONBVUWPD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (naphthalen-2-yl)boronic acid
• IUPAC Traditional name: naphthalen-2-ylboronic acid
• Synonyms: 2-Naphthaleneboronic acid; 2-Naphthylboronic acid; 2-naphthylboronic acid; Naphthalene-2-boronic acid; 2-Naphthalene boronic acid; 2-Naphthaleneboronic acid; 2-Naphthylboronic caid; 2-Naphthaleneboronic acid; 2-萘硼酸; 2-萘基硼酸; 2-萘硼酸

Database IDs

• CAS Number: 32316-92-0
• MDL Number: MFCD00236051
• Beilstein Number: 2936449
• PubChem SID: 160973353; 24886134; 24871549
• PubChem CID: 2734375

CALCULATED PROPERTIES

• Acid pKa: 8.704878
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.6417305
• LogD (pH = 7.4): 2.6211052
• Log P: 2.642
• Molar Refractivity: 47.0537 cm^3
• Polarizability: 21.112686 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 267-268°C; 269-275 °C; 269-275 °C(lit.); ca 267°C

Safety Information

• Storage Warning: IRRITANT; Irritant/Keep Cold/Store under Argon
• 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: ≥95.0%; ≥97.0% (HPLC); 97%
• Grade: purum
• Linear Formula: C10H7B(OH)2

DETAILS

Sigma Aldrich - 480134

Application
Used in a study of an enantioselective rhodium-catalyzed addition of aryl boronic acids to 2,2,2-trifluoroacetophenones leading to chiral, tertiary trifluoromethyl alcohols.1 Also employed in a study of a palladium-catalyzed addition of aryl boronic acids to nitriles providing aryl ketones and to aryloxy nitriles providing benzofurans.2
Other Notes
Contains varying amounts of anhydride
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 70875

Other Notes
Contains varying amounts of anhydride

REFERENCES

• Fluorescent PET receptor useful in saccharide detection: Tetrahedron Lett., 36, 4825 (1995); Pure Appl. Chem., 68, 2179 (1996). Reagent for selective fluorescence detection of F^-: Chem. Commun., 1365 (1998). For boronic acid chemistry, see Appendix 5.