2-Chloroethanol

2-Chloroethanol

Ball and stick model of 2-chloroethanol Spacefill model of 2-chloroethanol
Names
IUPAC name 2-Chloroethanol
Other names Chloroethanol 2-Chloro-1-ethanol β-Chloroethanol δ-Chloroethanol 2-Chloroethyl alcohol Ethylchlorhydrin Ethylene chlorohydrin Glycol chlorohydrin Glycol monochlorohydrin 2-Hydroxyethyl chloride β-Hydroxyethyl chloride 2-Monochloroethanol
Identifiers
CAS Number	107-07-3 Y
3DMet	B01042
Beilstein Reference	878139
ChEBI	CHEBI:28200 Y
ChEMBL	ChEMBL191244 Y
ChemSpider	21106015 Y
EC Number	203-459-7
Gmelin Reference	25389
Jmol 3D model	Interactive image
KEGG	C06753 Y
MeSH	Ethylene+Chlorohydrin
PubChem	34
RTECS number	KK0875000
UNII	753N66IHAN Y
UN number	1135
InChI InChI=1S/C2H5ClO/c3-1-2-4/h4H,1-2H2 Y Key: SZIFAVKTNFCBPC-UHFFFAOYSA-N Y
SMILES OCCCl
Properties
Chemical formula	C2H5ClO
Molar mass	80.51 g·mol−1
Appearance	Colourless liquid
Odor	faint, ether-like
Density	1.201 g mL−1
Melting point	−62.60 °C; −80.68 °F; 210.55 K
Boiling point	127 to 131 °C; 260 to 268 °F; 400 to 404 K
Solubility in water	miscible
log P	−0.107
Vapor pressure	700 Pa (at 20 °C)
Refractive index (nD)	1.441
Thermochemistry
Std enthalpy of combustion (ΔcHo298)	−1.1914 MJ mol−1
Vapor pressure	{{{value}}}
Related compounds
Related compounds	Chloromethane Chloroiodomethane Bromochloromethane Dibromochloromethane Isobutyl chloride 2-Bromo-1-chloropropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

2-Chloroethanol is an chemical compound with the formula HOCH₂CH₂Cl and the simplest chlorohydrin. 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.

Synthesis and applications

2-Chloroethanol is produced by treating ethylene with hypochlorous acid:

Synthesis of 2-chlorethanol by treating ethylene with hypochlorous acid

2-Chloroethanol was once produced on a large scale as a precursor to ethylene oxide:

Synthesis of ethylene oxide from 2-chloroethanol

This application has been supplanted by the greener direct oxidation of ethylene. Otherwise chloroethanol is used in a number of specialized applications. Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol. 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.

Environmental aspects

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.

Safety

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.

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.