From Wikipedia, the free encyclopedia
2,2,2-Trichloroethanol
2,2,2-Trichloroethanol
2,2,2-Trichloroethanol
Names
Preferred IUPAC name
2,2,2-Trichloroethan-1-ol
Identifiers
1697495
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.003.701
EC Number
2407
KEGG
UNII
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
Properties
C2 H3 Cl3 O
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 :
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 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).
Chemical compound
2,2,2-Trichloroethanol is the
chemical compound with
formula Cl3 C−CH2 OH . 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
^
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
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tribromoethanol ,
trichloroethanol ,
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Alkylbenzene sulfonate
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Xenon
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4-Phenyl-4-formyl-N-methylpiperidine
αEMBTL
Bicuculline
Brucine
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Negative modulators:
Amiloride
Benzodiazepines (e.g.,
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diazepam ,
flunitrazepam ,
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Corymine
Cyanotriphenylborate
Daidzein
Dihydropyridines (e.g.,
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Furosemide
Genistein
Ginkgo constituents (e.g.,
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ginkgolide C ,
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Imipramine
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