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Merck

142077

Sigma-Aldrich

2,2,2-Trichloroethyl chloroformate

98%

Sinónimos:

2,2,2-Trichloroethoxycarbonyl chloride

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About This Item

Fórmula lineal:
ClCOOCH2CCl3
Número de CAS:
Peso molecular:
211.86
Beilstein/REAXYS Number:
970619
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor pressure

0.06 psi ( 20 °C)

assay

98%

form

liquid

refractive index

n20/D 1.471 (lit.)

bp

171-172 °C (lit.)

density

1.539 g/mL at 25 °C (lit.)

functional group

chloro

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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General description

2,2,2-Trichloroethyl chloroformate (TrocCl) serves as a versatile reagent used for selective acylation and dealkylation in organic synthesis. It is used in regio, chemo, and stereoselective synthesis.

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.
  • It was used as starting reagent during the synthesis of 6-Nor-9,10-dihydrolysergic acid methyl ester.
  • It was used as reagent during N-demethylation of dextromethorphan.
  • It was used as protecting reagent for aliphatic and aromatic hydroxyl and amino groups.
Protecting reagent for aliphatic and aromatic hydroxyl and amino groups.

pictograms

Skull and crossbonesCorrosion

signalword

Danger

hcodes

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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


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2, 2, 2-Trichloroethyl Chloroformate (TrocCl)
EO dos Reis, et al.
Synlett, 2007, 1473-1474 (2007)
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
A simplified method for the gas chromatographic determination of pethidine and norpethidine after derivatization with trichloroethyl chloroformate.
P Hartvig et al.
Journal of chromatography, 274, 355-360 (1983-05-13)
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.
Therapeutic drug monitoring, 20(3), 313-318 (1998-06-19)
Mexiletine (Mexitil) is an antiarrhythmic agent used in the treatment of ventricular arrhythmia. The drug has a narrow therapeutic window, and monitoring its serum concentration is recommended. The authors describe a gas chromatography-mass spectrometric (GC/MS) assay of mexiletine using selected

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