(phenanthren-9-yl)boronic acid

• ChemBase ID: 32913
• Molecular Formular: C14H11BO2
• Molecular Mass: 222.04694
• Monoisotopic Mass: 222.08520999
• SMILES: c1cccc2c3ccccc3c(cc12)B(O)O
• Canonical SMILES: OB(c1cc2ccccc2c2c1cccc2)O
• InChI: InChI=1S/C14H11BO2/c16-15(17)14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9,16-17H
• InChIKey: JCDAUYWOHOLVMH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (phenanthren-9-yl)boronic acid
• IUPAC Traditional name: phenanthren-9-ylboronic acid
• Synonyms: Phenanthracene-9-boronic acid; 9-Phenanthracenylboronic acid; (9-Phenanthryl)boronic Acid; Phenanthren-9-ylboronic Acid; 9-Phenanthrenylboronic Acid; 9-Phenanthracenylboronic Acid; 9-Phenanthreneboronic Acid; Phenanthrene-9-boronic acid; Phenanthrene-9-boronic acid 98%; Phenanthrene-9-boronic acid; 菲-9-硼酸; 9-菲硼酸; 菲-9-硼酸

Database IDs

• CAS Number: 68572-87-2
• MDL Number: MFCD00143524
• PubChem SID: 160996220
• PubChem CID: 11775704

CALCULATED PROPERTIES

• Acid pKa: 8.553418
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.6438181
• LogD (pH = 7.4): 3.6148736
• Log P: 3.6442
• Molar Refractivity: 63.5039 cm^3
• Polarizability: 28.757895 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 165-170 °C; 165-170 °C; 254-256°C; 298-300°C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 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: 97%; 98%
• Empirical Formula (Hill Notation): C14H11BO2

DETAILS

Sigma Aldrich - 696552

Application
May contain varying amounts of anhydride
Reactant involved in the synthesis of:
• Large polycyclic aromatic hydrocarbons (PAHs)1,2
• Electron rich benzo[g,h,i]perylenes3
• FLAP protein inhibitors as antiinflammatory agents4
• Aminoisoquinolinones as PARP-2 selective inhibitors5Reactant involved in homocoupling reactions6
Packaging
5 g in glass bottle

Toronto Research Chemicals - P294810

9-Phenanthreneboronic Acid is used as an fluorescent analytical reagent in sensing systems for glucose-specific detection.

REFERENCES

• Kanekiyo, Y. et al.: Chem. Lett., 35, 852 (2006)
• Yum, K. et al.: ACS Nano, Pages Ahead of Print;