2,2,2-Trichloroethanol
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Names | |||
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Preferred IUPAC name
2,2,2-Trichloroethan-1-ol | |||
Identifiers | |||
CAS Number
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3D model (JSmol)
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Beilstein Reference
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1697495 | ||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.003.701 ![]() | ||
EC Number |
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Gmelin Reference
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2407 | ||
IUPHAR/BPS
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KEGG | |||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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InChI
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SMILES
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Properties | |||
Chemical formula
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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 | |||
Safety data sheet (SDS) | [1] | ||
GHS labelling: | |||
Pictograms
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Signal word
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Danger | ||
Hazard statements
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H302, H315, H318, H336 | ||
Precautionary statements
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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 [1] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
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Infobox references | |||
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]
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]
![2,2,2-trichloroethanol protecting group.png](http://upload.wikimedia.org/wikipedia/commons/thumb/f/f0/2%2C2%2C2-trichloroethanol_protecting_group.png/280px-2%2C2%2C2-trichloroethanol_protecting_group.png)
See also[]
- 1,1,1-Trichloroethane
- Tribromoethanol
- Triclofos
References[]
- ^ a b c d e "Material Safety Data Sheet- 2,2,2-Trichloroethanol, 98%" Online document at the Cole-Parmer website. Accessed on 2020-07-11.
- ^ "2,2,2-Trichloroethanol ≥99%". Online product catalog page at Merck website. Accessed on 2020-07-11.
- ^ The Merck Index, 13th Edition.
- ^ 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.
- ^ 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.
- ^ 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
- Primary alcohols
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