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17341-93-4 - 2,2,2-Trichloroethyl chloroformate, 97% - Chloroformic acid 2,2,2-trichloroethyl ester - 2,2,2-Trichloroethoxycarbonyl chloride - L06875 - Alfa Aesar

L06875 2,2,2-Trichloroethyl chloroformate, 97%

CAS Number
17341-93-4
Synonyms
Chloroformic acid 2,2,2-trichloroethyl ester
2,2,2-Trichloroethoxycarbonyl chloride

Size Price ($) Quantity Availability
25g 37.50
100g 120.00
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2,2,2-Trichloroethyl chloroformate, 97%

MDL
MFCD00000810
EINECS
241-363-7

Chemical Properties

Formula
ClCO2CH2CCl3
Formula Weight
211.86
Melting point
0-2°
Boiling Point
171-172°
Flash Point
>100°(212°F)
Density
1.539
Refractive Index
1.4700
Sensitivity
Moisture Sensitive
Solubility
Soluble in Ether, Benzene, Chloroform, Ethanol. Insoluble in water.

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.

Notes

Moisture Sensitive. Desiccate at 4°C. Store under inert gas. Incompatible materials are Strong oxidizing agents.

Literature References

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.

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.

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).

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).

Effective reagent for dehydration of primary amides to nitriles: Synth. Commun., 30, 3047 (2000).

For a brief survey of uses of this reagent in synthesis, see: Synlett, 1473 (2007).

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H330-H314-H318

Toxic if swallowed. Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P260-P284-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear respiratory protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment is urgent (see label). Rinse mouth. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
970619
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2915.90
TSCA
Yes

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