2-Chloroethanol

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]

2-Chloroethanol

Skeletal formula of 2-chloroethanol
Ball and stick model of 2-chloroethanol Spacefill model of 2-chloroethanol
Names
Preferred IUPAC name 2-Chloroethan-1-ol[1]
Other names 2-Chloroethanol[1] beta-Chloroethanol[2] 2-Chloro-1-ethanol[2] β-Chloroethanol[2] δ-Chloroethanol[2] 2-Chloroethyl alcohol[2] Ethyl chlorhydrin[2] Ethylene chlorohydrin[2] Glycol chlorohydrin[2] Glycol monochlorohydrin[2] 2-Hydroxyethyl chloride[2] β-Hydroxyethyl chloride[2] 2-Monochloroethanol[2]
Identifiers
CAS Number	107-07-3 Y
3D model (JSmol)	Interactive image
Beilstein Reference	878139
ChEBI	CHEBI:28200 Y
ChEMBL	ChEMBL191244 Y
ChemSpider	21106015 Y
ECHA InfoCard	100.003.146
EC Number	203-459-7
Gmelin Reference	25389
KEGG	C06753 Y
MeSH	Ethylene+Chlorohydrin
PubChem CID	34
RTECS number	KK0875000
UNII	753N66IHAN Y
UN number	1135
CompTox Dashboard (EPA)	DTXSID1021877
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	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
Solubility in water	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:
Pictograms
Signal word	Danger
Hazard statements	H226, H300+H310+H330
Precautionary statements	P260, P280, P284, P301+P310, P302+P350
NFPA 704 (fire diamond)	4 2 0
Flash point	55 °C (131 °F; 328 K)
Autoignition temperature	425 °C (797 °F; 698 K)
Explosive limits	5–16%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	67 mg/kg (dermal, rabbit)[citation needed] 72 mg/kg (rat, oral) 81 mg/kg (mouse, oral) 71 mg/kg (rat, oral) 110 mg/kg (guinea pig, oral)[4]
LC50 (median concentration)	7.5 ppm (rat, 1 h) 32 ppm (rat, 4 h) 260 ppm (guinea pig) 33 ppm (rat, 4 h) 87 ppm (rat) 115 ppm (mouse)[4]
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	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

Synthesis and applications

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:

HOCH₂CH₂Cl + NaOH → C₂H₄O + NaCl + H₂O

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.

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.^[10]

Safety

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]}