3-Bromo-2-methoxy-propene Property

solubility 

Soluble in common organic solvents (i.e. diethyl ether, THF).

Hazard and Precautionary Statements (GHS)

3-Bromo-2-methoxy-propene Chemical Properties,Usage,Production

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.