|Preferred IUPAC name
3D model (JSmol)
|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)
Std enthalpy of
|−1.1914 MJ mol−1|
|GHS signal word||DANGER|
|H226, H300, H310, H330|
|P260, P280, P284, P301+310, P302+350|
|Flash point||55 °C (131 °F; 328 K)|
|425 °C (797 °F; 698 K)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|67 mg kg−1 (dermal, rabbit)
72 mg/kg (rat, oral)
81 mg/kg (mouse, oral)
71 mg/kg (rat, oral)
110 mg/kg (guinea pig, oral)
LC50 (median concentration)
|7.5 ppm (rat, 1 hr)
32 ppm (rat, 4 hr)
260 ppm (guinea pig)
33 ppm (rat, 4 hr)
87 ppm (rat)
115 ppm (mouse)
|US health exposure limits (NIOSH):|
|TWA 5 ppm (16 mg/m3) [skin]|
|C 1 ppm (3 mg/m3) [skin]|
IDLH (Immediate danger)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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 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.
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.
- Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 29. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001.
For example, the omission of the locant ‘1’ in 2-chloroethanol, while permissible in general usage, is not allowed in preferred IUPAC names, thus the name 2-chloroethan-1-ol is the PIN.
- Depositor-supplied synonyms for CID 34
- "NIOSH Pocket Guide to Chemical Hazards #0268". National Institute for Occupational Safety and Health (NIOSH).
- "Ethylene chlorohydrin". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
- 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
- "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Retrieved October 29, 2011.