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T54801

Sigma-Aldrich

2,2,2-Trichloroethanol

ReagentPlus®, ≥99%

Synonym(s):

Trichloroethyl alcohol

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About This Item

Linear Formula:
Cl3CCH2OH
CAS Number:
115-20-8
Molecular Weight:
149.40
Beilstein/REAXYS Number:
1697495
EC Number:
204-071-0
MDL number:
MFCD00004677
UNSPSC Code:
12352100
PubChem Substance ID:
24900284
NACRES:
NA.22

vapor density

5.16 (vs air)

Quality Level

200

vapor pressure

1 mmHg ( 20 °C)

product line

ReagentPlus®

assay

≥99%

refractive index

n20/D 1.49 (lit.)

bp

152-154 °C (lit.)

mp

17.8 °C (lit.)

density

1.56 g/mL at 20 °C (lit.)

SMILES string

OCC(Cl)(Cl)Cl

InChI

1S/C2H3Cl3O/c3-2(4,5)1-6/h6H,1H2

InChI key

KPWDGTGXUYRARH-UHFFFAOYSA-N

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Application

The 2,2,2-Trichloroethyl (TCE) moiety of 2,2,2-trichloroethanol is mainly used as a protecting group for acids, acetals and also phosphoryl groups of nucleotides. It can be easily cleaved by zinc reduction.
Some of its other application include:
  • Conversion of per-O-acetylated sugars to per-O-acetylated trichloroethyl derivatives.
  • Preparation of TCE ester of chlorosulfuric acid.
  • Preparation of 2,2,2-trichloroethyl acetimidate hydrochloride.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - STOT SE 3

target_organs

Central nervous system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB0473
STBL2408
STBL0808
STBL0807
STBK6569

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e-EROS Encyclopedia of Reagents for Organic Synthesis null
Preparation of N1?Phenylacetamidine 4?Bromobenzoate Using 2, 2, 2?Trichloroethyl Acetimidate Hydrochloride.
Wei L & Caron S.
Organic Syntheses, 174-181 null
2, 2, 2-Trichloroethyl chloroformate: a general reagent for demethylation of tertiary methylamines.
Montzka TA, et al.
Tetrahedron Letters, 15(14), 1325-1327 (1974)
Sophie Scheidecker et al.
Human mutation, 40(10), 1826-1840 (2019-05-23)
Mutations in genes encoding aminoacyl-tRNA synthetases have been reported in several neurological disorders. KARS is a dual localized lysyl-tRNA synthetase and its cytosolic isoform belongs to the multiple aminoacyl-tRNA synthetase complex (MSC). Biallelic mutations in the KARS gene were described
Anand Chopra et al.
Scientific reports, 9(1), 13923-13923 (2019-09-29)
The incorporation of 2,2,2-trichloroethanol in polyacrylamide gels allows for fluorescent visualization of proteins following electrophoresis. Ultraviolet-light exposure, in the presence of this trichlorinated compound, results in a covalent modification of the tryptophan indole ring that shifts the fluorescent emission into
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