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
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About This Item
Empirical Formula (Hill Notation):
C6H7BrO2
CAS Number:
Molecular Weight:
191.02
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22
Quality Level
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
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.
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.
(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.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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