Chloroacetaldehyde

Chloroacetaldehyde
Structural formula	Ball-and-stick model
Names
	IUPAC name Chloroacetaldehyde
	Systematic IUPAC name Chloroethanal
Identifiers
CAS Number	107-20-0 ;
ChemSpider	32;
ECHA InfoCard	100.003.158
CompTox Dashboard (EPA)	DTXSID4020292 ;
Properties
Chemical formula	C2H3Cl
Molar mass	78.50 g mol-1
Appearance	Colourless liquid
Boiling point	85–85.5 °C
Solubility in water	Soluble as hydrate
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	alkylating agent
Related compounds
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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

^ ^a ^b 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
^ 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

[Ullmann-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

[1]

[2]