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142077

Sigma-Aldrich

2,2,2-Trichloroethyl chloroformate

98%

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:
24848380
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.)

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
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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
2, 2, 2-Trichloroethyl Chloroformate (TrocCl)
EO dos Reis, et al.
Synlett, 2007, 1473-1474 (2007)
Greene, T.W. Wuts, P.G.M.
Protective Groups in Organic Synthesis (1991)
Giampietro Frison et al.
Rapid communications in mass spectrometry : RCM, 19(7), 919-927 (2005-03-05)
A new analytical approach, based on derivatization with 2,2,2-trichloroethyl chloroformate and gas chromatography/mass spectrometry (GC/MS), was investigated for qualitative and quantitative analyses of a large range of amphetamine-related drugs and ephedrines in plasma, urine and hair samples. Sample preparation involved
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