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2,2,2-Trichloroethanol

2,2,2-Trichloroethanol

2,2,2-Trichloroethanol is the chemical compound with formula . Its molecule can be described as that of ethanol, with the three hydrogen atoms at position 2 (the methyl group) replaced by chlorine atoms. It is a clear flammable liquid at room temperature, colorless when pure but often with a light yellow color.

The pharmacological effects of this compound in humans are similar to those of its prodrug chloral hydrate, and of chlorobutanol. Historically, it has been used as a sedative hypnotic. 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-Trichloroethanol can be added to SDS-PAGE gels in order to enable fluorescent detection of proteins without a staining step, for immunoblotting or other analysis methods.

Use in organic synthesis

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

References

References

  1. "[https://pim-resources.coleparmer.com/sds/75723.pdf Material Safety Data Sheet- 2,2,2-Trichloroethanol, 98%]" Online document at the Cole-Parmer website. Accessed on 2020-07-11.
  2. "[https://www.sigmaaldrich.com/catalog/DataSheetPage.do?brandKey=ALDRICH&symbol=T54801 2,2,2-Trichloroethanol ≥99%]". Online product catalog page at Merck website. Accessed on 2020-07-11.
  3. ''The Merck Index'', 13th Edition.
  4. (March 2004). "Visible fluorescent detection of proteins in polyacrylamide gels without staining". Analytical Biochemistry.
  5. Lowder, Patrick D.. (2001-04-15). "Encyclopedia of Reagents for Organic Synthesis". John Wiley & Sons, Ltd.
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