2,2,2-Trichloroethanol

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2,2,2-Trichloroethanol is the chemical compound with formula Template:Chem2. 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.[1][2]

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.[3] 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.[4]

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.[5]

Use in organic synthesis

2,2,2-Trichloroethanol is an effective protecting group for carboxylic acids due to its ease in addition and removal.[6]

File:2,2,2-trichloroethanol protecting group.png

See also

References

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  2. "2,2,2-Trichloroethanol ≥99%". Online product catalog page at Merck website. Accessed on 2020-07-11.
  3. The Merck Index, 13th Edition.
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