2,2,2-Trichloroethanol

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
CAS Number
3D model (JSmol)
Beilstein Reference
 1697495
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.701
EC Number
  • 204-071-0
Gmelin Reference
 2407
IUPHAR/BPS
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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
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
 GHS05: CorrosiveGHS07: Exclamation mark
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).
checkY verify (what is checkY☒N ?)
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]

See also

References

  1. ^ 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. ^ "2,2,2-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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