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1-Chloroethyl chloroformate
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1-chloroethyl chloroformate.svg 1-Chloroethyl carbonochloridate α-chloroethyl chloroformate 50893-53-3 correct 256-834-2 521305 454726 2L3UG3R4FD ClC(OC(Cl)C)=O 1S/C3H4Cl2O2/c1-2(4)7-3(5)6/h2H,1H3 QOPVNWQGBQYBBP-UHFFFAOYSA-N
3 4 2 2 https://www.sigmaaldrich.com/GB/en/sds/aldrich/301485?userType=anonymous Sigmaaldrich.com Safety data sheet: 1-chloroethyl chloroformate 2025-06-30
2-Chloroethyl chloroformate Chloromethyl chloroformate Ethyl chloroformate chloroformates
1-Chloroethyl chloroformate (chemical formula: C3H4Cl2O2) has a structure consisting of ethyl chloroformate with a chloro group as substituent on the ethyl group and has two enantiomeric forms. It can be used for N-dealkylation of tertiary amines.10.1021/jo00185a072 A new reagent for the selective, high-yield N-dealkylation of tertiary amines: Improved syntheses of naltrexone and nalbuphine 1984 Olofson R. A. Martz Jonathan T. Senet Jean Pierre Piteau Marc Malfroot Thierry The Journal of Organic Chemistry 49 11 2081–2082
Synthesis
1-Chloroethyl chloroformate can be manufactured by the reaction of acetaldehyde with phosgene in the presence of benzyltributylammonium chloride.10.1002/047084289X.rc102 1-Chloroethyl Chloroformate Encyclopedia of Reagents for Organic Synthesis 2001 Armstrong Alan 0-471-93623-5 or various other catatysts.10.1081/SCC-120021030 2003 33 12 Flosser David A. Olofson Roy A. Improved Synthesis of Dialkylaminopyrrolines Synthetic Communications 2045–2052
Uses
1-Chloroethyl chloroformate is a useful reagent, for example for the N-dealkylation of tertiary amines, especially their demethylation to produce drug metabolites for forensic investigations.10.1016/S0379-0738(96)02088-9 Preparation of N-demethylated drug metabolites for analytical purposes using 1-chloroethyl chloroformate 1997 Pelander Anna Ojanperä Ilkka a. Hase Tapio Forensic Science International 85 3 193–198
References
Category:Chloroformates
Category:Chloroethyl compounds