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	115-20-8 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1697495
ChEBI	CHEBI:28094 ;
ChEMBL	ChEMBL1171 ;
ChemSpider	7961 ;
ECHA InfoCard	100.003.701
EC Number	204-071-0;
Gmelin Reference	2407
IUPHAR/BPS	2293;
KEGG	C07490 ;
PubChem CID	8259;
UNII	AW835AJ62N ;
CompTox Dashboard (EPA)	DTXSID1021950 ;
	InChI InChI=1S/C2H3Cl3O/c3-2(4,5)1-6/h6H,1H2 Key: KPWDGTGXUYRARH-UHFFFAOYSA-N ; 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 °C (64.0 °F; 290.9 K)
Boiling point	151 °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)
Safety data sheet (SDS)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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]

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

[parmer-1] "Material Safety Data Sheet- 2,2,2-Trichloroethanol, 98%" Online document at the Cole-Parmer website. Accessed on 2020-07-11.

[sigma-2] "2,2,2-Trichloroethanol ≥99%". Online product catalog page at Merck website. Accessed on 2020-07-11.

[Merck-3] The Merck Index, 13th Edition.

[BudavariO'Neil1996-4] 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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Use in organic synthesis

See also

References