(1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol

• ChemBase ID: 137759
• Molecular Formular: C12H12O2
• Molecular Mass: 188.22248
• Monoisotopic Mass: 188.08372962
• SMILES: c1ccc(cc1)C1=CC=C[C@@H]([C@@H]1O)O
• Canonical SMILES: O[C@H]1[C@@H](O)C=CC=C1c1ccccc1
• InChI: InChI=1S/C12H12O2/c13-11-8-4-7-10(12(11)14)9-5-2-1-3-6-9/h1-8,11-14H/t11-,12+/m0/s1
• InChIKey: UMAHGMFKBJHGME-NWDGAFQWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol
• IUPAC Traditional name: (1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol
• Synonyms: (1S-cis)-3-Phenyl-3,5-cyclohexadiene-1,2-diol; (1S-顺)-3-苯基-3,5-环己二烯-1,2-二醇

Database IDs

• CAS Number: 66008-24-0
• MDL Number: MFCD01863538
• PubChem SID: 162232020; 24872336
• PubChem CID: 5459789

CALCULATED PROPERTIES

• Acid pKa: 13.27459
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.3096601
• LogD (pH = 7.4): 1.3096595
• Log P: 1.3096601
• Molar Refractivity: 56.9392 cm^3
• Polarizability: 21.480234 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 79-84 °C(lit.)
• Optical Rotation: [α]20/D +220°, c = 1.064 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

Product Information

• Purity: 98%
• Concentration: 0.2 g/mL in 0.1 M phosphate buffer
• Empirical Formula (Hill Notation): C12H12O2

DETAILS

Sigma Aldrich - 489638

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.