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

• ChemBase ID: 5888
• Molecular Formular: C10H10O2
• Molecular Mass: 162.1852
• Monoisotopic Mass: 162.06807956
• SMILES: O[C@H]1[C@@H](O)C=Cc2c1cccc2
• 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-VHSXEESVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S)-1,2-dihydronaphthalene-1,2-diol
• IUPAC Traditional name: (1R,2S)-1,2-dihydronaphthalene-1,2-diol
• Synonyms: (1R-cis)-1,2-Dihydro-1,2-naphthalenediol; (1R,2S)-cis-1,2-Dihydro-1,2-dihydroxynaphthalene; (1R,2S)-cis-1,2-Dihydro-1,2-naphthalenediol; (1R, 2S)-CIS 1,2 DIHYDROXY-1,2-DIHYDRONAPHTHALENE; (1R-顺)-1,2-二氢-1,2-萘二醇; (1R,2S)-顺-1,2-二氢-1,2-二羟基萘; (1R,2S)-顺-1,2-二氢-1,2-萘二醇

Database IDs

• CAS Number: 51268-88-3
• MDL Number: MFCD00216514
• Beilstein Number: 1909468
• PubChem SID: 160969315; 99444735; 24863205
• PubChem CID: 440294

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 0.63
• LOG S: -0.86
• Solubility (Water): 2.25e+01 g/l

PROPERTIES

Physical Property

• Melting Point: 121-127 °C(lit.); 136-139 °C
• Optical Rotation: [α]20/D +242±5°, c = 1% in chloroform stab. with amylenes; [α]22/D +229°, c = 1 in methanol
• pH: 8.5(adjusted to)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0%; 98%
• Concentration: 0.067 g/mL in 0.1 M phosphate buffer
• Empirical Formula (Hill Notation): C10H10O2

DETAILS

DrugBank - DB08264

Drug information: experimental

Sigma Aldrich - 37342

Other Notes
Chiral building block for preparing both enantiomers of 1,2-epoxy-1,2,3,4-tetrahydro- naphthalene1

Sigma Aldrich - 490326

Reconstitution
To recover the pure product from the suspension:(1)Thaw the frozen suspension and filter the solid. (2) Rinse bottle with a few milliliters of base-washed (aqueous Na2CO3) ethyl acetate. (3) Use the rinsing to wash the solid. (4) Collect solid. (5) To further collect more product from the filtrate: extract filtrate with equal volumes of base-washed (aqueous Na2CO3) ethyl acetate (repeat three times). (6) Dry the ethyl acetate extract over MgSO4. (7) Evaporate the solvent - DO NOT HEAT! (8) Combine solids collected from the suspension and the filtrate. Pure crystals should be stored at -78° C. A suspension of the product in phosphate buffer is stable at 0° C.
Physical form
A suspension in phosphate buffer.