| 2-Chloroethanol | |
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2-Chloroethanol |
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Other names
2-chloroethyl alcohol, ethylene chlorohydrin, glycol chlorohydrin, 2-chloro-1-ethanol, 2-monochloroethanol, 2-hydroxyethyl chloride, β-chloroethanol, β-hydroxyethyl chloride, chloroethanol, δ-chloroethanol, ethylchlorhydrin, ethylene chlorohydrin, glycol monochlorohydrin |
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| Identifiers | |
| CAS number | 107-07-3 |
| ChemSpider | 21106015 |
| UNII | 753N66IHAN |
| KEGG | C06753 |
| ChEBI | CHEBI:28200 |
| ChEMBL | CHEMBL191244 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C2H5ClO |
| Molar mass | 80.52 g/mol |
| Density | 1.197 g/cm³ |
| Melting point |
-67 °C |
| Boiling point |
128-130 °C |
| Related compounds | |
| Related compounds | 2-Fluoroethanol |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
2-Chloroethanol is an organochlorine compound with the formula HOCH2CH2Cl. This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional groups.
Contents |
2-Chloroethanol is produced by treating ethylene with hypochlorous acid:
2-Chloroethanol was once produced on a large scale as a precursor to ethylene oxide:
This application has been supplanted by the greener direct oxidation of ethylene. Otherwise chloroethanol is used in a number of specialized applications.[1] Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol.[2] It is a building block in the production of pharmaceuticals, biocides and plasticizers. It is also used for manufacture of thiodiglycol. It is a solvent for cellulose acetate and ethyl cellulose, textile printing dyes, in dewaxing, refining of rosin, extraction of pine lignin, and the cleaning of machines.
Chloroethanol is a metabolite in the degradation of 1,2-dichloroethane. The alcohol is then further oxidized via chloroacetaldehyde to chloroacetate. This metabolic pathway is topical since billions of kilograms of 1,2-dichloroethane are processed annually as a precursor to vinyl chloride.[3]
2-Chloroethanol is toxic with an LD50 of 89 mg/kg in rats. Like most organochlorine compounds, chloroethanol combusts to yield hydrogen chloride and phosgene.