Chloroacetaldehyde

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Chloroacetaldehyde
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 107-20-0 YesY, (hydrate: 34789-09-8, 7737-02-2)
ChemSpider 32
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula C2H3Cl
Molar mass 78.50 g mol-1
Appearance Colourless liquid
Boiling point

85–85.5 °C

Solubility in water Soluble as hydrate
style="background: #F8EABA; text-align: center;" colspan="2" | Hazards
Main hazards alkylating agent
style="background: #F8EABA; text-align: center;" colspan="2" | Related compounds
Related compounds 2-chloroethanol, Chloroacetic acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Chloroacetaldehyde is the 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 hydrate (acetal), ClCH2CH(OH)2. Chloroacetaldehyde is a useful intermediate in the synthesis, e.g. of pharmaceutical compounds.

Synthesis and reactions

The hydrate of chloroacetaldehyde is produced by the oxidation of aqueous vinyl chloride using chlorine:

ClCH=CH2 + Cl2 + H2O → ClCH3CH2OH + 2 HCl

It can also be prepared from vinyl acetate.[1]

Being bifunctional, chloroacetaldehyde is a versatile precursor to many heterocyclic compounds. It condenses with thiourea derivatives to give aminothiazoles. This reaction was once important as a precursor to sulfathiazole, one of the first sulfa drugs.[1]

Environmental aspects

Chloroacetaldehyde is a metabolite in the degradation of 1,2-dichloroethane, which initially converts to chloroethanol. This metabolic pathway is topical since billions of kilograms of 1,2-dichloroethane have been produced as a precursor to vinyl chloride.[2]

References

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  1. 1.0 1.1 Reinhard Jira, Erwin Kopp, Blaine C. McKusick, Gerhard Röderer, Axel Bosch, Gerald Fleischmann “Chloroacetaldehydes“ in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a06_527.pub2
  2. Janssen, D. B.; van der Ploeg, J. R. and Pries, F., "Genetics and biochemistry of 1,2-dichloroethane degradation", Biodegradation, 1994, 5, 249-57.doi:10.1007/BF00696463