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	115-20-8 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1697495
ChEBI	CHEBI:28094 Y
ChEMBL	ChEMBL1171 Y
ChemSpider	7961 Y
ECHA InfoCard	100.003.701
EC Number	204-071-0
Gmelin Reference	2407
IUPHAR/BPS	2293
KEGG	C07490 Y
PubChem CID	8259
UNII	AW835AJ62N Y
CompTox Dashboard (EPA)	DTXSID1021950
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

• 1,1,1-Trichloroethane
• Tribromoethanol
• Triclofos