2,2,2-Trichloroethanol Explained

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.^[1]

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.^[2] 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.^[3]

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.^[4]

Use in organic synthesis

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

See also

• 1,1,1-Trichloroethane
• Tribromoethanol
• Triclofos

Notes and References

1. "2,2,2-Trichloroethanol ≥99%". Online product catalog page at Merck website. Accessed on 2020-07-11.
2. The Merck Index, 13th Edition.
3. Book: S. Budavari. M. O'Neil. Ann Smith . P. Heckelman . J. Obenchain . The Merck Index . Merck Index . 12th print . 15 March 1996 . Taylor & Francis . 978-0-911910-12-4.
4. Ladner. Carol. Visible fluorescent detection of proteins in polyacrylamide gels without staining. Analytical Biochemistry. March 2004. 326. 1. 13–20. 10.1016/j.ab.2003.10.047. 14769330.