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2,2,2-Trichloroethanol

From Wikipedia, the free encyclopedia
2,2,2-Trichloroethanol
2,2,2-Trichloroethanol
2,2,2-Trichloroethanol
2,2,2-Trichloroethanol
2,2,2-Trichloroethanol
Names
Preferred IUPAC name
2,2,2-Trichloroethan-1-ol
Identifiers
3D model (JSmol)
1697495
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.003.701Edit this at Wikidata
EC Number
  • 204-071-0
2407
KEGG
UNII
  • InChI=1S/C2H3Cl3O/c3-2(4,5)1-6/h6H,1H2 checkY
    Key: KPWDGTGXUYRARH-UHFFFAOYSA-N checkY
  • InChI=1/C2H3Cl3O/c3-2(4,5)1-6/h6H,1H2
    Key: KPWDGTGXUYRARH-UHFFFAOYAW
  • ClC(Cl)(Cl)CO
Properties
C2H3Cl3O
Molar mass149.40 g/mol
Density1.55 g/cm3
Melting point17.8[1] °C (64.0 °F; 290.9 K)
Boiling point151[1] °C (304 °F; 424 K)
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302,H315,H318,H336
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 point88 °C (190 °F; 361 K)[1]
Safety data sheet (SDS)[1]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

2,2,2-Trichloroethanol is thechemical compound withformulaCl3C−CH2OH. Itsmolecule can be described as that ofethanol, with the threehydrogen atoms at position 2 (themethyl group) replaced bychlorine 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 itsprodrugchloral hydrate, and ofchlorobutanol. Historically, it has been used as a sedative hypnotic.[3] The hypnotic drugtriclofos (2,2,2-trichloroethyl phosphate) is metabolizedin vivo to 2,2,2-trichloroethanol. Chronic exposure may result in kidney and liver damage.[4]

2,2,2-Trichloroethanol can be added toSDS-PAGE gels in order to enablefluorescent detection ofproteins without a staining step, forimmunoblotting or other analysis methods.[5]

Use in organic synthesis

[edit]

2,2,2-Trichloroethanol is an effectiveprotecting group forcarboxylic acids due to its ease in addition and removal.[6]

See also

[edit]

References

[edit]
  1. ^abcde"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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