2,2,2-Trichloroethanol

2,2,2-Trichloroethanol is the chemical compound with formula Cl3C−CH2OH. 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]

2,2,2-Trichloroethanol
2,2,2-Trichloroethanol
2,2,2-Trichloroethanol
Names
Preferred IUPAC name
2,2,2-Trichloroethan-1-ol
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference
 1697495
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.701
EC Number
  • 204-071-0
Gmelin Reference
 2407
KEGG
PubChem CID
UNII
InChI
  • InChI=1S/C2H3Cl3O/c3-2(4,5)1-6/h6H,1H2 Y
    Key: KPWDGTGXUYRARH-UHFFFAOYSA-N Y
  • InChI=1/C2H3Cl3O/c3-2(4,5)1-6/h6H,1H2
    Key: KPWDGTGXUYRARH-UHFFFAOYAW
SMILES
  • ClC(Cl)(Cl)CO
Properties
Chemical formula
 C2H3Cl3O
Molar mass 149.40 g/mol
Density 1.55 g/cm3
Melting point 17.8[1] °C (64.0 °F; 290.9 K)
Boiling point 151[1] °C (304 °F; 424 K)
Hazards
GHS labelling:
Pictograms
Signal word
 Danger
Hazard statements
 H302, H315, H318, H336
Precautionary statements
 P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P362, P403+P233, P405, P501
Flash point 88 °C (190 °F; 361 K)[1]
Safety data sheet (SDS) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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]

See also

References
  1. "Material Safety Data Sheet- 2,2,2-Trichloroethanol, 98%" Online document at the Cole-Parmer website. Accessed on 2020-07-11.
  2. "2,2,2-Trichloroethanol ≥99%". Online product catalog page at Merck website. Accessed on 2020-07-11.
  3. The Merck Index, 13th Edition.
  4. 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.
  5. 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.
  6. 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 978-0471936237


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