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2,2,2-Trichloroethanol

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2,2,2-Trichloroethanol
2,2,2-Trichloroethanol
2,2,2-Trichloroethanol
2,2,2-Trichloroethanol
2,2,2-Trichloroethanol
Names
IUPAC name
2,2,2-Trichloroethanol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.701 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C2H3Cl3O/c3-2(4,5)1-6/h6H,1H2 checkY
    Key: KPWDGTGXUYRARH-UHFFFAOYSA-N checkY
  • InChI=1/C2H3Cl3O/c3-2(4,5)1-6/h6H,1H2
    Key: KPWDGTGXUYRARH-UHFFFAOYAW
  • ClC(Cl)(Cl)CO
Properties
C2H3Cl3O
Molar mass 149.40 g/mol
Density 1.55 g/cm3
Melting point 17.8 °C (64.0 °F; 290.9 K)
Boiling point 151 °C (304 °F; 424 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

2,2,2-Trichloroethanol is an organic compound related to ethanol, except the hydrogen atoms at position 2 are replaced with chlorine atoms. In humans, its pharmacological effects are similar to those of its prodrugs, chloral hydrate and chlorobutanol. It has, historically, been used as a sedative hypnotic.[1] The hypnotic drug triclofos (2,2,2-trichloroethyl phosphate) is metabolized in vivo to 2,2,2-trichloroethanol. Chronic exposure may result in kidney and liver damage.[2] 2,2,2-Trichloroethanol can be added to SDS-PAGE gels in order to enable fluorescent detection of proteins without a staining step. This imaging step is compatible with later analysis by, e.g., immunoblotting.[3]

Use in organic synthesis

2,2,2-trichloroethanol is an effective protecting group for carboxylic acids due to its ease in addition and removal.[4]

See also

References

  1. ^ The Merck Index, 13th Edition.
  2. ^ S. Budavari; M. O'Neil; Ann Smith; P. Heckelman; J. Obenchain (15 March 1996). The Merck Index (12th print ed.). Taylor & Francis. ISBN 978-0-911910-12-4.
  3. ^ Ladner, Carol (March 2004). "Visible fluorescent detection of proteins in polyacrylamide gels without staining". Analytical Biochemistry. 326 (1): 13–20. doi:10.1016/j.ab.2003.10.047. PMID 14769330.
  4. ^ Lowder, Patrick D. (2001-04-15), "2,2,2-Trichloroethanol", Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Ltd, doi:10.1002/047084289x.rt203, ISBN 0471936235, retrieved 2018-09-25


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