Chloroacetaldehyde
chemical compound
Chloroacetaldehyde is an organic compound with the formula ClCH2CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous alkylating agent. The compound is not normally encountered in the anhydrous form, but rather as the hemiacetal (ClCH2CH(OH))2.
Chloroacetaldehyde is a metabolite of the antineoplastic ifosfamide and believed to be responsible for some of the toxicity observed with ifosfamide.
Synthesis and occurrence
Hydrated chloroacetaldehyde is produced by the chlorination of aqueous vinyl chloride:
ClCH=CH2 + Cl2 + H2O → ClCH2CHO + 2 HCl
It can also be prepared from vinyl acetate or by careful chlorination of acetaldehyde. The related bromoacetaldehyde is prepared via bromination of vinyl acetate. It also rapidly forms an acetals in the presence of alcohols.
Water free chloroacetaldehyde is prepared from the hydrate by azeotropic distillation with chloroform, toluene, or carbon tetrachloride. Anhydrous chloroacetaldehyde reversibly converts to polyacetals. Less reactive chloroacetaldehyde derivatives might be used instead to obtain chloroacetaldehyde or bypass its intermediate formation completely: e.g. chloroacetaldehyde dimethyl acetal (2-chloro-1,1-dimethoxyethane) hydrolyzes in acidic conditions to give chloroacetaldehyde, which may then quickly react with the other reagents instead of polymerizing.
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