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23258

Sigma-Aldrich

2,2,2-Trichloroethyl chloroformate

purum, ≥98.0% (NT)

Synonym(s):

2,2,2-Trichloroethoxycarbonyl chloride

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About This Item

Linear Formula:
ClCOOCH2CCl3
CAS Number:
17341-93-4
Molecular Weight:
211.86
Beilstein:
970619
EC Number:
241-363-7
MDL number:
MFCD00000810
UNSPSC Code:
12352100
PubChem Substance ID:
329752403
NACRES:
NA.22

vapor pressure

0.06 psi ( 20 °C)

Quality Level

200

grade

purum

Assay

≥98.0% (NT)

refractive index

n20/D 1.471 (lit.)
n20/D 1.471

bp

171-172 °C (lit.)

density

1.539 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

ClC(=O)OCC(Cl)(Cl)Cl

InChI

1S/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2

InChI key

LJCZNYWLQZZIOS-UHFFFAOYSA-N

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Application

2,2,2-Trichloroethyl chloroformate was used as:
  • derivatizing reagent in gas chromatographic/mass spectrometric determination of a large range of amphetamine-related drugs and ephedrines in plasma, urine and hair samples
  • starting reagent during the synthesis of 6-nor-9,10-dihydrolysergic acid methyl ester (IV)
  • reagent during N-demethylation of dextromethorphan
  • protecting group reagent for amines and alcohols

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H314,H331

Hazard Classifications

Acute Tox. 3 Inhalation - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK9661
BCCH9853
BCCF3814
BCCC2921
BCCB6437

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M. Imoto et al.
Bulletin of the Chemical Society of Japan, 60, 2205-2205 (1987)
F. Farina et al.
Tetrahedron Letters, 32, 1109-1109 (1991)
X.S. He et al.
Synthetic Communications, 20, 2177-2177 (1990)
A M Crider et al.
Journal of pharmaceutical sciences, 70(12), 1319-1321 (1981-12-01)
6-Nor-9,10-dihydrolysergic acid methyl ester (IV) was prepared by demethylation of 9,10-dihydrolysergic acid methyl ester (II) with 2,2,2-trichloroethyl chloroformate, followed by reduction of the intermediate carbamate (III) with zinc in acetic acid. The 6-ethyl-V and 6-n-propyl-VI derivatives were prepared by alkylation
A Dasgupta et al.
American journal of clinical pathology, 109(5), 527-532 (1998-05-12)
Amphetamine and methamphetamine are commonly abused central nervous system stimulants. We describe a rapid new derivatization of amphetamine and methamphetamine using 2,2,2-trichloroethyl chloroformate for gas chromatography-mass spectrometric analysis. Amphetamine and methamphetamine, along with N-propyl amphetamine (internal standard), were extracted from
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