(naphthalen-1-yl)boronic acid

• ChemBase ID: 8742
• Molecular Formular: C10H9BO2
• Molecular Mass: 171.98826
• Monoisotopic Mass: 172.06955993
• SMILES: OB(O)c1c2c(ccc1)cccc2
• Canonical SMILES: OB(c1cccc2c1cccc2)O
• InChI: InChI=1S/C10H9BO2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7,12-13H
• InChIKey: HUMMCEUVDBVXTQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (naphthalen-1-yl)boronic acid
• IUPAC Traditional name: naphthalen-1-ylboronic acid
• Synonyms: Naphthalene-1-boronic acid; α-Naphthaleneboronic acid; α-Naphthylboronic acid; 1-naphthalenyl-boronic acid; NSC 78936; 1-Naphthaleneboronic acid; 1-Naphthylboronic acid; Naphthalene-1-boronic acid; 1-Naphthylboronic acid; 1-Naphthylboronic acid; 1-Naphthaleneboronic acid; 1-Naphthaleneboronic acid; (naphthalen-1-yl)boronic acid; 1-Borononaphthalene; 1-萘基硼酸; 1-萘硼酸; 萘-1-硼酸; 1-萘基硼酸; 1-萘硼酸

Database IDs

• CAS Number: 13922-41-3
• MDL Number: MFCD00019722
• Beilstein Number: 2937504
• PubChem SID: 24897577; 160972049
• PubChem CID: 254532

CALCULATED PROPERTIES

• Acid pKa: 8.605715
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.6416614
• LogD (pH = 7.4): 2.6159031
• Log P: 2.642
• Molar Refractivity: 47.0537 cm^3
• Polarizability: 21.114271 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~210 °C; 204-210°C; 204-210°C; 208-214 °C(lit.); 210-211°C; 213 - 214°C
• Hydrophobicity(logP): 2.769

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; 26-37-60
• 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%; ≥95.0% (HPLC); 95%; 97%
• Grade: purum
• Linear Formula: C10H7B(OH)2
• Empirical Formula (Hill Notation): C10H9BO2

DETAILS

Sigma Aldrich - N257

Other Notes
Contains varying amounts of anhydride
Packaging
5, 25 g in glass bottle

REFERENCES

• The Suzuki coupling with a protected L-tyrosine triflate, catalyzed by Tetrakis(triphenylphosphine)palladium(0), 10548, occurred in high yield without racemization when anhydrous K₂CO₃ in toluene was used as the base: J. Org. Chem., 57, 379 (1992). For Ni-catalyzed coupling with allylamines, see: J. Chem. Soc., Perkin 1, 2083 (1995). See Appendix 5.