489492

(1S-cis)-3-Bromo-3,5-cyclohexadiene-1,2-diol

0.2 g/mL in 0.1 M phosphate buffer, 96%

• Synonym(s): (1S,2S)-3-Bromo-3,5-cyclohexadiene-1,2-diol
• Empirical Formula (Hill Notation): C₆H₇BrO₂
• CAS Number: 130792-45-9
• Molecular Weight: 191.02
• MDL number: MFCD00216512
• UNSPSC Code: 12352002
• PubChem Substance ID: 24872488
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 96%
• optical activity: [α]22/D +20°, c = 1 in methanol
• concentration: 0.2 g/mL in 0.1 M phosphate buffer
• pH: 8.5(adjusted to)
• mp: 90-94 °C (lit.)
• functional group: bromo; hydroxyl
• storage temp.: −20°C
• SMILES string: O[C@H]1C=CC=C(Br)[C@H]1O
• InChI: 1S/C6H7BrO2/c7-4-2-1-3-5(8)6(4)9/h1-3,5-6,8-9H/t5-,6+/m0/s1
• InChI key: KLPGXZKAVBGFGF-NTSWFWBYSA-N

Description

General description

(1S-cis)-3-Bromo-3,5-cyclohexadiene-1,2-diol is a chiral cis-dienediol employed as a key building block for the preparation of varieties of natural products. It can undergo few chemical reactions like cycloadditions, sigmatropic rearrangements, electrophilic additions, and oxidative cleavage.[1][2]

Physical form

A suspension in phosphate buffer.

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)