1-Chloroethyl chloroformate

Last updated
1-Chloroethyl chloroformate
1-chloroethyl chloroformate.svg
Names
IUPAC name
1-Chloroethyl carbonochloridate
Other names
α-chloroethyl chloroformate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.051.650 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 256-834-2
PubChem CID
UNII
  • InChI=1S/C3H4Cl2O2/c1-2(4)7-3(5)6/h2H,1H3
    Key: QOPVNWQGBQYBBP-UHFFFAOYSA-N
  • ClC(OC(Cl)C)=O
Properties
C3H4Cl2O2
Molar mass 142.96 g·mol−1
Hazards
Safety data sheet (SDS) [1]
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

Contents

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

  1. ↑ "Safety data sheet: 1-chloroethyl chloroformate". Sigmaaldrich.com. Retrieved 2025-06-30.
  2. 1 2 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. 1 2 Armstrong, Alan (2001). "1-Chloroethyl Chloroformate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc102. ISBN   0-471-93623-5.
  4. ↑ Flosser, David A.; Olofson, Roy A. (2003). "Improved Synthesis of Dialkylaminopyrrolines". Synthetic Communications. 33 (12): 2045–2052. doi:10.1081/SCC-120021030.
  5. ↑ 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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