Chemical Properties
Colorless liquid. Boiling point 136 ℃. not soluble in water.
Uses
Used for organic synthesis.
Reactivity Profile
3-Bromo-2-methoxy-propene is a three-carbon electrophile in alkylations; three-carbon component in arene cycloadditions; bromoacetone equivalent; cyclopentenone annulation reagent; acetone equivalent in nucleophilic additions.
Synthesis
3-Bromo-2-methoxy-propene is prepared by reacting 1-bromo-2,2-dimethoxypropane with diisopropylethylamine-p-toluenesulfonate heated in methanol at 134-137°C.
Precautions
Neat 2-methoxyallyl bromide is unstable at rt and sensitive to moisture. Mixtures obtained from the thermal cracking of 1-bromo-2,2-dimethoxypropane have been stored for extended periods at -20 °C. Alternatively, a 50% solution in CCl4 may be stored over Na2CO3 at rt in the dark. Caution: This is an alkylation reagent; proper protective equipment should be worn, and its use should be restricted to a fume hood.
