Chloroacetaldehyde
| Chloroacetaldehyde | |
|---|---|
| Chloroacetaldehyde | |
| Chloroethanal | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 107-20-0  , (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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<references />, or <references group="..." />- ↑ 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
- ↑ 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
