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Chemical compound From Wikipedia, the free encyclopedia
2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin).[6] 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 group.[7]
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Names | |||
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Preferred IUPAC name
2-Chloroethan-1-ol[1] | |||
Other names | |||
Identifiers | |||
3D model (JSmol) |
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3DMet | |||
878139 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.003.146 | ||
EC Number |
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25389 | |||
KEGG | |||
MeSH | Ethylene+Chlorohydrin | ||
PubChem CID |
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RTECS number |
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UNII | |||
UN number | 1135 | ||
CompTox Dashboard (EPA) |
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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] | |||
log P | −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) |
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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 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Chloroethanol is produced by treating ethylene with hypochlorous acid:[7]
2-Chloroethanol was once produced on a large scale as a precursor to ethylene oxide:
This application has been supplanted by the more economic direct oxidation of ethylene. Otherwise chloroethanol is still used in the production of pharmaceuticals, biocides, and plasticizers.[7] Many of these applications entail its use in installing 2-hydroxyethyl groups.[8] Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol.[9] 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.[10]
2-Chloroethanol is toxic with an LD50 of 89 mg/kg in rats. Like most organochlorine compounds, chloroethanol releases hydrochloric acid and phosgene when burned.
In regards to dermal exposure to 2-chloroethanol, the Occupational Safety and Health Administration has set a permissible exposure limit of 5 ppm (16 mg/m3) over an eight-hour time-weighted average, while the National Institute for Occupational Safety and Health has a more protective recommended exposure limit of a 1 ppm (3 mg/m3) exposure ceiling.[11]
It is classified as an extremely 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]
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