|Jmol-3D images||Image 1|
|Molar mass||80.51 g mol−1|
|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|
|Vapor pressure||700 Pa (at 20 °C)|
|Refractive index (nD)||1.441|
|Std enthalpy of
|−1.1914 MJ mol−1|
|GHS signal word||DANGER|
|GHS hazard statements||H226, H300, H310, H330|
|GHS precautionary statements||P260, P280, P284, P301+310, P302+350|
|Flash point||55 °C; 131 °F; 328 K|
|Autoignition temperature||425 °C; 797 °F; 698 K|
|LD50||67 mg kg−1 (dermal, rabbit)|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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 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. 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.
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.
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.
- Depositor-supplied synonyms for CID 34
- Gordon Y. T. Liu, W. Frank Richey, Joanne E. Betso “Chlorohydrins“ in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a06_565
- Roderich Raue and John F. Corbett “Nitro and Nitroso Dyes“ in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_383
- 1. Janssen, D. B.; van der Ploeg, J. R. and Pries, F., "Genetics and Biochemistry of 1,2-Dichloroethane Degradation", Biodegradation, 1994, volume 5, pp. 249-57.doi:10.1007/BF00696463
- CDC - NIOSH Pocket Guide to Chemical Hazards