2-Chloroethanol

2-Chloroethanol

Names
IUPAC name 2-Chloroethanol
Other names Chloroethanol[1] 2-Chloro-1-ethanol[1] β-Chloroethanol[1] δ-Chloroethanol[1] 2-Chloroethyl alcohol[1] Ethylchlorhydrin[1] Ethylene chlorohydrin[1] Glycol chlorohydrin[1] Glycol monochlorohydrin[1] 2-Hydroxyethyl chloride[1] β-Hydroxyethyl chloride[1] 2-Monochloroethanol[1]
Identifiers
3DMet	B01042
Beilstein Reference	878139
CAS Registry Number	107-07-3 Y
ChEBI	CHEBI:28200 Y
ChEMBL	ChEMBL191244 Y
ChemSpider	21106015 Y
EC number	203-459-7
Gmelin Reference	25389
InChI InChI=1S/C2H5ClO/c3-1-2-4/h4H,1-2H2 Y Key: SZIFAVKTNFCBPC-UHFFFAOYSA-N Y
Jmol-3D images	Image
KEGG	C06753 Y
MeSH	Ethylene+Chlorohydrin
PubChem	34
RTECS number	KK0875000
SMILES OCCCl
UNII	753N66IHAN Y
UN number	1135
Properties
Molecular 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 °C; 260 °F; 400 K
Solubility in water	miscible[2]
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
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H226, H300, H310, H330
GHS precautionary statements	P260, P280, P284, P301+310, P302+350
EU Index	603-028-00-7
EU classification	T+
R-phrases	R26/27/28
S-phrases	(S1/2), S45
NFPA 704	2 4 0
Flash point	55 °C (131 °F; 328 K)
Autoignition temperature	425 °C (797 °F; 698 K)
Explosive limits	5–16%
LD50 (Median lethal dose)	67 mg kg−1 (dermal, rabbit)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 5 ppm (16 mg/m3) [skin][2]
REL (Recommended)	C 1 ppm (3 mg/m3) [skin][2]
IDLH (Immediate danger)	7 ppm[2]
Related compounds
Related compounds	Chloromethane Chloroiodomethane Bromochloromethane Dibromochloromethane Isobutyl chloride 2-Bromo-1-chloropropane
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 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.

Synthesis and applications

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.^[3] Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol.^[4] 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.^[5]

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.^[6]

References