Neha Patil (Editor)

2 Chloroethanol

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Covid-19
3DMet  B01042
Formula  C2H5ClO
Density  1.2 g/cm³
Melting point  -67 °C
Appearance  Colourless liquid
Boiling point  128.7 °C
Molar mass  80.52 g/mol
2-Chloroethanol 2Chloroethanol CAS 107073 800945
Related compounds  Chloromethane Chloroiodomethane Bromochloromethane Dibromochloromethane Isobutyl chloride 2-Bromo-1-chloropropane

Synthesis of 2 chloroethanol


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.

Contents

2-Chloroethanol 2chloroethanollewispng

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:

2-Chloroethanol Acros Organics AC180960010 2Chloroethanol 99 1l 8819414 from

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.

2-Chloroethanol 2Chloroethanol107073IR2

An example is the reaction with theophylline to form Etofylline. Another example is the reaction with chlorphentermine to give Etolorex.

Environmental aspects

2-Chloroethanol wwwsigmaaldrichcomcontentdamsigmaaldrichstr

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.

Safety

2-Chloroethanol File2chloroethanolsvg Wikimedia Commons

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.

2-Chloroethanol 2Chloroethanol1122d4 98 atom D SigmaAldrich

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.

2-Chloroethanol 2Chloroethanol C2H5ClO ChemSpider

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.

2-Chloroethanol 2chloroethanol ChemSink

References

2-Chloroethanol Wikipedia


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