2,2,2-Trichloroethyl chloroformate, 97%, Thermo Scientific Chemicals
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2,2,2-Trichloroethyl chloroformate, 97%, Thermo Scientific Chemicals
Thermo Scientific Chemicals

2,2,2-Trichloroethyl chloroformate, 97%, Thermo Scientific Chemicals

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Catalog number L06875.22
also known as L06875-22
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Chemical Identifiers
CAS17341-93-4
IUPAC Name2,2,2-trichloroethyl carbonochloridate
Molecular FormulaC3H2Cl4O2
InChI KeyLJCZNYWLQZZIOS-UHFFFAOYSA-N
SMILESClC(=O)OCC(Cl)(Cl)Cl
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SpecificationsSpecification SheetSpecification Sheet
Appearance (Color)Clear colorless
Assay (GC)≥96.0%
Refractive Index1.4680-1.4720 @ 20?C
Identification (FTIR)Conforms
FormLiquid
2,2,2-Trichloroethyl chloroformate is used as a protecting reagent for aliphatic and aromatic hydroxyl and amino groups. It is 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, during N-demethylation of dextromethorphan. It was used as starting reagent during the synthesis of 6-Nor-9,10-dihydrolysergic acid methyl ester.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
2,2,2-Trichloroethyl chloroformate is used as a protecting reagent for aliphatic and aromatic hydroxyl and amino groups. It is 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, during N-demethylation of dextromethorphan. It was used as starting reagent during the synthesis of 6-Nor-9,10-dihydrolysergic acid methyl ester.

Solubility
Soluble in Ether, Benzene, Chloroform, Ethanol. Insoluble in water.

Notes
Moisture Sensitive. Desiccate at 4°C. Store under inert gas. Incompatible materials are Strong oxidizing agents.
RUO – Research Use Only

General References:

  1. Thomas A. Montzka; John D. Matiskella; R.A. Partyka. 2,2,2-trichloroethyl chloroformate: A general reagent for demethylation of tertiary methylamines.Tetrahedron Letters.1974,15 1325-1327.
  2. Giampietro Frison; Luciano Tedeschi; Donata Favretto; Aikebaier Reheman; Santo Davide Ferrara. Gas chromatography/mass spectrometry determination of amphetamine-related drugs and ephedrines in plasma, urine and hair samples after derivatization with 2,2,2-trichloroethyl chloroformate.Rapid Communications in Mass Spectrometry.2005,19 (7), 919-927.
  3. Reagent for the protection of OH groups as their trichloroethyl (Troc) carbonates, specifically cleaved by reduction with zinc: Tetrahedron Lett., 2555 (1967). For a systematic study of the protection of amines as their Troc-carbamates, see: Synthesis, 268 (1981).
  4. Preferred to ethyl chloroformate for the N-demethylation of tert-amines, since the resulting carbamate can be cleaved by reductive elimination: Tetrahedron Lett., 1325 (1974); Synth. Commun., 7, 79 (1977).
  5. Effective reagent for dehydration of primary amides to nitriles: Synth. Commun., 30, 3047 (2000).
  6. For a brief survey of uses of this reagent in synthesis, see: Synlett, 1473 (2007).