1-Chloroethyl chloroformate

1-Chloroethyl chloroformate
Names
	IUPAC name 1-Chloroethyl carbonochloridate
	Other names α-chloroethyl chloroformate
Identifiers
CAS Number	50893-53-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	454726;
ECHA InfoCard	100.051.650
EC Number	256-834-2;
PubChem CID	521305;
UNII	2L3UG3R4FD;
CompTox Dashboard (EPA)	DTXSID70965132 ;
	InChI InChI=1S/C3H4Cl2O2/c1-2(4)7-3(5)6/h2H,1H3 Key: QOPVNWQGBQYBBP-UHFFFAOYSA-N;
	SMILES ClC(OC(Cl)C)=O;
Properties
Chemical formula	C3H4Cl2O2
Molar mass	142.96 g·mol−1
Hazards
Safety data sheet (SDS)
Related compounds
Related chloroformates	2-Chloroethyl chloroformate; Chloromethyl chloroformate; Ethyl chloroformate;
	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". Sigmaaldrich.com. Retrieved 2025-06-30.
^ ^a ^b 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.
^ ^a ^b 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.

[1] "Safety data sheet: 1-chloroethyl chloroformate". Sigmaaldrich.com. Retrieved 2025-06-30.

[Olofson-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.

[Armstrong-3] 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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