2-Chloroethanol

changed changed 477213021 2-chloroethanol.svg correct ?? 150 Skeletal formula of 2-chloroethanol 2-chloroethanol-3D-balls.png correct ?? Ball and stick model of 2-chloroethanol 2-chloroethanol-3D-vdW.png correct ?? Spacefill model of 2-chloroethanol 2-Chloroethan-1-ol Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) Royal Society of Chemistry 2014 Cambridge 29 10.1039/9781849733069-FP001 978-0-85404-182-4 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. 2-Chloroethanol beta-ChloroethanolDepositor-supplied synonyms for CID 34. 2-Chloro-1-ethanol β-Chloroethanol δ-Chloroethanol 2-Chloroethyl alcohol Ethyl chlorhydrin Ethylene chlorohydrin Glycol chlorohydrin Glycol monochlorohydrin 2-Hydroxyethyl chloride β-Hydroxyethyl chloride 2-Monochloroethanol 107-07-3 correct CAS 34 21106015 correct chemspider 753N66IHAN correct FDA 203-459-7 1135 C06753 correct kegg Ethylene+Chlorohydrin 28200 correct EBI 191244 correct EBI KK0875000 878139 25389 B01042 OCCCl 1S/C2H5ClO/c3-1-2-4/h4H,1-2H2 correct chemspider SZIFAVKTNFCBPC-UHFFFAOYSA-N correct chemspider 2 5 1 1 Colourless liquid ether-like 1.201 g/mL 210.55 400–404 −0.107 700 Pa (at 20 °C) 1.441 Miscible −1.1914 MJ/mol Highly toxic and flammable flame skull and crossbones DANGER 226 300+310+330 260 280 284 301+310 302+350 4 2 0 55 425 5–16% 67mg/kg (dermal, rabbit)June 2015 72mg/kg (rat, oral) 81mg/kg (mouse, oral) 71mg/kg (rat, oral) 110mg/kg (guinea pig, oral)107073 Ethylene chlorohydrin 7.5ppm (rat, 1h) 32ppm (rat, 4h) 260ppm (guinea pig) 33ppm (rat, 4h) 87ppm (rat) 115ppm (mouse) TWA 5ppm (16mg/m3) [skin]0268 C 1ppm (3mg/m3) [skin] 7ppmhttp://www.newenv.com/resources/nfpa_chemicals New Environment Inc. NFPA Chemicals Chloromethane Chloroiodomethane Bromochloromethane Dibromochloromethane Isobutyl chloride 2-Bromo-1-chloropropane 2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula ClCH2CH2OH and the simplest beta-halohydrin (chlorohydrin).Ethylene chlorohydrin: properties 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. Synthesis and applications 2-Chloroethanol is produced by treating ethylene with hypochlorous acid: 400px|Synthesis of 2-chlorethanol by treating ethylene with hypochlorous acid 2-Chloroethanol was once produced on a large scale as a precursor to ethylene oxide: 280px|Synthesis of ethylene oxide from 2-chloroethanol ClCH2CH2OH + 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.Gordon Y. T. Liu W. Frank Richey Joanne E. Betso Brian Hughes Joanna Klapacz Joerg Lindner 3 Chlorohydrins 2014 10.1002/14356007.a06_565.pub2 Many of these applications entail its use in installing 2-hydroxyethyl groups.Organic Syntheses Butler J Kellogg R Synthesis of Macrocyclic Sulfides Using Cesium Thiolates: 1,4,8,11-Tetrathiacyclotetradecane 1987 65 150 150 10.15227/orgsyn.065.0150 free Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol.Roderich Raue John F. Corbett Nitro and Nitroso Dyes 2002 10.1002/14356007.a17_383 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. Janssen D. B. van der Ploeg J. R. Pries F. 1994 Genetics and Biochemistry of 1,2-Dichloroethane Degradation https://pure.rug.nl/ws/files/14528144/1994BiodegradJanssen.pdf Biodegradation 5 3–4 249–57 10.1007/BF00696463 7765836 475768 Safety 2-Chloroethanol is toxic with an 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 5ppm (16mg/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 1ppm (3mg/m3) exposure ceiling.CDC - NIOSH Pocket Guide to Chemical Hazards 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.Government Printing Office Code of Federal Regulations 40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf July 1, 2008 October 29, 2011 https://web.archive.org/web/20120225051612/http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf February 25, 2012February 2020 References Category:Primary alcohols Category:Chloroethyl compounds Category:Chloroethanols