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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

Stock No. Size Price ($) Quantity Availability
L06875-14 25g 39.40
L06875-22 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
Storage & Sensitivity
Keep Cold. 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: H302-H314-H331-H335

Harmful if swallowed. Causes severe skin burns and eye damage. Toxic if inhaled. May cause respiratory irritation.

Precautionary Statements: P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P501c

Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. 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. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

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

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