2,2,2-Trichloroethyl chloroformate

Clear light yellow liquid

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
• starting reagent during the synthesis of 6-nor-9,10-dihydrolysergic acid methyl ester (IV)
• reagent during N-demethylation of dextromethorphan
• protecting group reagent for amines and alcohols

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.

2,2,2-Trichloroethyl chloroformate is a protecting agent for various functional groups; a net carboxylating agent for organometallic reagents; achieves N-demethylation and N-debenzylation of tertiary amines; and activates N-heteroaromatic rings for reaction with organostannanes.

2,2,2-Trichloroethyl chloroformate is widely available commercially. It can be readily prepared by passing Phosgene into a solution of 2,2,2- Trichloroethanol in benzene/diethylaniline or benzene/ether/pyridine. An alternate two-step approach (93% yield) has  been described that employs S-Ethyl Chlorothioformate instead of phosgene.