(1S,2S)-1,2-dihydronaphthalene-1,2-diol

• ChemBase ID: 142636
• Molecular Formular: C10H10O2
• Molecular Mass: 162.1852
• Monoisotopic Mass: 162.06807956
• SMILES: c1ccc2c(c1)C=C[C@@H]([C@H]2O)O
• Canonical SMILES: O[C@H]1C=Cc2c([C@@H]1O)cccc2
• InChI: InChI=1S/C10H10O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6,9-12H/t9-,10-/m0/s1
• InChIKey: QPUHWUSUBHNZCG-UWVGGRQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S)-1,2-dihydronaphthalene-1,2-diol
• IUPAC Traditional name: (1S,2S)-1,2-dihydronaphthalene-1,2-diol
• Synonyms: (1S-trans)-1,2-Dihydro-1,2-dihydroxynaphthalene; (1S,2S)-trans-1,2-Dihydro-1,2-naphthalenediol; (1R,2R)-rel-1,2-Dihydro-1,2-naphthalenediol; trans-1,2-Naphthalenedihydrodiol; rac trans-1,2-Dihydroxy-1,2-dihydronaphthalene; (1S-反)-1,2-二氢-1,2-二羟基萘; (1S,2S)-反-1,2-二氢-1,2-萘二醇

Database IDs

• CAS Number: 13011-97-7; 771-16-4
• MDL Number: MFCD15143657
• Beilstein Number: 1909467
• PubChem SID: 162236862
• PubChem CID: 114831

CALCULATED PROPERTIES

• Acid pKa: 13.200536
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.99647117
• LogD (pH = 7.4): 0.99647045
• Log P: 0.99647117
• Molar Refractivity: 47.3798 cm^3
• Polarizability: 18.027025 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Off-White to Gray Solid
• Melting Point: 95-98°C (65°C transition)

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96.0% (HPLC)
• Optical Purity: enantiomeric excess: ≥97.0%
• Empirical Formula (Hill Notation): C10H10O2

DETAILS

Sigma Aldrich - 713937

Packaging
250 mg in glass bottle

Toronto Research Chemicals - D452735

Naphthalene metabolite

REFERENCES

• Sun, Y., et al.: Arch. Toxicol., 80, 280 (2006)
• Cho, T., et al.: Drug Metab. Drug Interact., 22, 235 (2006)
• Iwamoto, N., et al.: J. Biol. Chem., 282, 33396 (2006)