Chemistry:1-Chloroethyl chloroformate
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| Names | |
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| Preferred IUPAC name
1-Chloroethyl carbonochloridate | |
| Other names
α-chloroethyl chloroformate
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| Identifiers | |
3D model (JSmol)
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| Properties | |
| C3H4Cl2O2 | |
| Molar mass | 142.96 g·mol−1 |
| Hazards | |
| Safety data sheet | [1] |
| Related compounds | |
Related chloroformates
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
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.[2]
Synthesis
1-Chloroethyl chloroformate can be manufactured by the reaction of acetaldehyde with phosgene in the presence of benzyltributylammonium chloride.[3] or various other catatysts.[4]
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.[2][3][5]
References
- ↑ "Safety data sheet: 1-chloroethyl chloroformate". https://www.sigmaaldrich.com/GB/en/sds/aldrich/301485?userType=anonymous.
- ↑ 2.0 2.1 Olofson, R. A.; Martz, Jonathan T.; Senet, Jean Pierre; Piteau, Marc; Malfroot, Thierry (1984). "A new reagent for the selective, high-yield N-dealkylation of tertiary amines: Improved syntheses of naltrexone and nalbuphine". The Journal of Organic Chemistry 49 (11): 2081–2082. doi:10.1021/jo00185a072.
- ↑ 3.0 3.1 Armstrong, Alan (2001). "1-Chloroethyl Chloroformate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc102. ISBN 0-471-93623-5.
- ↑ Flosser, David A.; Olofson, Roy A. (2003). "Improved Synthesis of Dialkylaminopyrrolines". Synthetic Communications 33 (12): 2045–2052. doi:10.1081/SCC-120021030.
- ↑ Pelander, Anna; Ojanperä, Ilkka; a. Hase, Tapio (1997). "Preparation of N-demethylated drug metabolites for analytical purposes using 1-chloroethyl chloroformate". Forensic Science International 85 (3): 193–198. doi:10.1016/S0379-0738(96)02088-9.
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