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 ;
3D model (JSmol)	Interactive image;
3DMet	B01042;
Beilstein Reference	878139
ChEBI	CHEBI:28200 ;
ChEMBL	ChEMBL191244 ;
ChemSpider	21106015 ;
ECHA InfoCard	100.003.146
EC Number	203-459-7;
Gmelin Reference	25389
KEGG	C06753 ;
MeSH	Ethylene+Chlorohydrin
PubChem CID	34;
RTECS number	KK0875000;
UNII	753N66IHAN ;
UN number	1135
CompTox Dashboard (EPA)	DTXSID1021877 ;
	InChI InChI=1S/C2H5ClO/c3-1-2-4/h4H,1-2H2 Key: SZIFAVKTNFCBPC-UHFFFAOYSA-N ;
	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 (ΔcH⦵298)	−1.1914 MJ mol−1
Hazards
	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−1 (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)
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)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 5 ppm (16 mg/m3) [skin]
REL (Recommended)	C 1 ppm (3 mg/m3) [skin]
IDLH (Immediate danger)	7 ppm
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). verify (what is ?) 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:

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.^[6] Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol.^[7] 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.^[8]

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.^[9]

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.^[10]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Depositor-supplied synonyms for CID 34
^ "2-Chloroethanol". Pubchem. 27 May 2015. Retrieved 27 May 2015.
^ ^a ^b ^c ^d NIOSH Pocket Guide to Chemical Hazards. "#0268". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b "Ethylene chlorohydrin". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ http://www.newenv.com/resources/nfpa_chemicals
^ 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. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: postscript (link)

[pubchem-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Depositor-supplied synonyms for CID 34

[2] "2-Chloroethanol". Pubchem. 27 May 2015. Retrieved 27 May 2015.

[PGCH-3] NIOSH Pocket Guide to Chemical Hazards. "#0268". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-4] "Ethylene chlorohydrin". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[5] ttp://www.newenv.com/resources/nfpa_chemicals

[6] 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

[7] 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

[8] 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

[9] CDC - NIOSH Pocket Guide to Chemical Hazards

[gov-right-know-10] "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. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: postscript (link)

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