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1-Chloroethyl chloroformate

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.

Synthesis

1-Chloroethyl chloroformate can be manufactured by the reaction of acetaldehyde with phosgene in the presence of benzyltributylammonium chloride. or various other catatysts.

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.

References

References

  1. "Safety data sheet: 1-chloroethyl chloroformate".
  2. (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.
  3. (2001). "Encyclopedia of Reagents for Organic Synthesis".
  4. (2003). "Improved Synthesis of Dialkylaminopyrrolines". Synthetic Communications.
  5. (1997). "Preparation of ''N''-demethylated drug metabolites for analytical purposes using 1-chloroethyl chloroformate". Forensic Science International.
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chloroformates chloroethyl-compounds
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