 | |||
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name 2-Chloroethan-1-ol[1] | |||
| Other names | |||
| Identifiers | |||
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3D model (JSmol) | |||
| 878139 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
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| ECHA InfoCard | 100.003.146 | ||
| EC Number |
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| 25389 | |||
| KEGG |
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| MeSH | Ethylene+Chlorohydrin | ||
| RTECS number |
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| UNII | |||
| UN number | 1135 | ||
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| Properties | |||
| C2H5ClO | |||
| Molar mass | 80.51 g·mol−1 | ||
| Appearance | Colourless liquid | ||
| Odor | ether-like | ||
| Density | 1.201 g/mL | ||
| Melting point | −62.60 °C; −80.68 °F; 210.55 K | ||
| Boiling point | 127–131 °C; 260–268 °F; 400–404 K | ||
| Miscible[3] | |||
| logP | −0.107 | ||
| Vapor pressure | 700 Pa (at 20 °C) | ||
Refractive index (nD) | 1.441 | ||
| Thermochemistry | |||
Std enthalpy of combustion(ΔcH⦵298) | −1.1914 MJ/mol | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards | Highly toxic and flammable | ||
| GHS labelling: | |||
  | |||
| Danger | |||
| H226,H300+H310+H330 | |||
| P260,P280,P284,P301+P310,P302+P350 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 55 °C (131 °F; 328 K) | ||
| 425 °C (797 °F; 698 K) | |||
| Explosive limits | 5–16% | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
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LC50 (median concentration) | |||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) | TWA 5 ppm (16 mg/m3) [skin][3] | ||
REL (Recommended) | C 1 ppm (3 mg/m3) [skin][3] | ||
IDLH (Immediate danger) | 7 ppm[3] | ||
| Related compounds | |||
Related compounds | |||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
2-Chloroethanol (also calledethylene chlorohydrin orglycol chlorohydrin) is an organicchemical compound with thechemical formula HOCH2CH2Cl and thesimplestbeta-halohydrin (chlorohydrin).[6] This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both analkyl chloride and analcoholfunctional group.[7]
2-Chloroethanol is produced by treatingethylene withhypochlorous acid:[7]
2-Chloroethanol was once produced on a large scale as a precursor toethylene oxide:
This application has been supplanted by the more economic directoxidation ofethylene. Otherwise chloroethanol is still used in the production ofpharmaceuticals,biocides, andplasticizers.[7] Many of these applications entail its use in installing 2-hydroxyethyl groups.[8] Severaldyes are prepared by thealkylation ofaniline derivatives with chloroethanol.[9] It is also used for manufacture ofthiodiglycol.
It is asolvent forcellulose acetate andethyl cellulose, textile printing dyes, in dewaxing, refining ofrosin, extraction ofpinelignin, and the cleaning of machines.
Chloroethanol is ametabolite in the degradation of1,2-dichloroethane. The alcohol is then further oxidized viachloroacetaldehyde to chloroacetate. This metabolic pathway is topical since billions of kilograms of 1,2-dichloroethane are processed annually as a precursor tovinyl chloride.[10]
2-Chloroethanol is toxic with anLD50 of 89 mg/kg in rats. Like most organochlorine compounds, chloroethanol releaseshydrochloric acid andphosgene when burned.
In regards to dermal exposure to 2-chloroethanol, theOccupational Safety and Health Administration has set apermissible exposure limit of 5 ppm (16 mg/m3) over an eight-hour time-weighted average, while theNational Institute for Occupational Safety and Health has a more protectiverecommended exposure limit of a 1 ppm (3 mg/m3) exposure ceiling.[11]
It is classified as anextremely hazardous substance in the United States as defined in Section 302 of the U.S.Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[12][failed verification]
For example, the omission of the locant '1' in 2-chloroethanol, while permissible in general usage, is not allowed in preferred IUPAC names, thus the name 2-chloroethan-1-ol is the PIN.
| Authority control databases: National |
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