(1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol

• ChemBase ID: 148505
• Molecular Formular: C6H7BrO2
• Molecular Mass: 191.02258
• Monoisotopic Mass: 189.96294146
• SMILES: C1=C[C@@H]([C@@H](C(=C1)Br)O)O
• Canonical SMILES: O[C@H]1[C@@H](O)C=CC=C1Br
• InChI: InChI=1S/C6H7BrO2/c7-4-2-1-3-5(8)6(4)9/h1-3,5-6,8-9H/t5-,6+/m0/s1
• InChIKey: KLPGXZKAVBGFGF-NTSWFWBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol
• IUPAC Traditional name: (1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol
• Synonyms: (1S-cis)-3-Bromo-3,5-cyclohexadiene-1,2-diol; (1S-顺式)-3-溴-3,5-环己二烯-1,2-二醇

Database IDs

• CAS Number: 130792-45-9
• MDL Number: MFCD00216512
• PubChem SID: 24872488; 162242680
• PubChem CID: 11830237

CALCULATED PROPERTIES

• Acid pKa: 12.706408
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.19523248
• LogD (pH = 7.4): 0.19523036
• Log P: 0.19523251
• Molar Refractivity: 40.0964 cm^3
• Polarizability: 14.701455 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 90-94 °C(lit.)
• Optical Rotation: [α]22/D +20°, 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: -20°C

Product Information

• Purity: 96%
• Concentration: 0.2 g/mL in 0.1 M phosphate buffer
• Empirical Formula (Hill Notation): C6H7BrO2

DETAILS

Sigma Aldrich - 489492

Packaging
5 g in poly bottle
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.