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489492

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

Name: (1<I>S</I>-<I>cis</I>)-3-Bromo-3,5-cyclohexadiene-1,2-diol
Brand: ALDRICH

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:

130792-45-9

Molecular Weight:

191.02

MDL number:

MFCD00216512

UNSPSC Code:

12352002

PubChem Substance ID:

24872488

NACRES:

NA.22

Pricing and availability is not currently available.

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

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.

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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