2-Chloroethyl chloroformate

2-Chloroethyl chloroformate
Names
	IUPAC name 2-Chloroethyl carbonochloridate
	Other names β-chloroethyl chloroformate
Identifiers
CAS Number	627-11-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	11802;
ECHA InfoCard	100.009.985
EC Number	210-982-4;
PubChem CID	12305;
UNII	4D32H07Z9I ;
UN number	3277
CompTox Dashboard (EPA)	DTXSID2060832 ;
	InChI InChI=1S/C3H4Cl2O2/c4-1-2-7-3(5)6/h1-2H2 Key: SVDDJQGVOFZBNX-UHFFFAOYSA-N;
	SMILES ClC(=O)OCCCl;
Properties
Chemical formula	C3H4Cl2O2
Molar mass	142.96 g·mol−1
Appearance	colourless liquid
Density	1.3847
Boiling point	155 °C (311 °F; 428 K)
Refractive index (nD)	1.4483
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H301, H314, H315, H319, H331, H335
Precautionary statements	P260, P261, P264, P264+P265, P270, P271, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P319, P321, P330, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, P501
Flash point	70 °C (158 °F; 343 K)
Safety data sheet (SDS)
Related compounds
Related chloroformates	1-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

2-Chloroethyl chloroformate (chemical formula: C₃H₄Cl₂O₂) has a structure consisting of ethyl chloroformate with a chloro group as substituent on the ethyl group.

Synthesis

2-Chloroethyl chloroformate is the sole product of the reaction between ethylene oxide and phosgene in the presence of a small amount of pyridine.^[2]

Uses

2-Chloroethyl chloroformate is commonly used as a reagent,^[3]^[4] especially for making derivatives of amines and carboxylic acids for analysis by gas chromatography.^[5]^[6]

References

^ "Safety data sheet: 2-chloroethyl chloroformate". Sigmaaldrich.com. Retrieved 2025-06-30.
^ Jones, J. Idris (1957). "530. The reaction of carbonyl chloride with 1 : 2-epoxides". Journal of the Chemical Society (Resumed): 2735. doi:10.1039/JR9570002735.
^ Mousseau, James J. (2011). "β-Chloroethyl Chloroformate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01309. ISBN 978-0-471-93623-7.
^ Wu, Yikang; Shen, Xin (2000). "A high-yielding low-cost facile synthesis of 2-oxazolidinones chiral auxiliaries". Tetrahedron: Asymmetry. 11 (21): 4359–4363. doi:10.1016/S0957-4166(00)00415-8.
^ Vreeken, Rob J.; Jager, Maria E.; Ghijsen, Rudy T.; Brinkman, Udo A. Th. (1992). "The derivatization of fatty acids by (Chloro)alkyl chloroformates in non-aqueous and aqueous media for GC analysis". Journal of High Resolution Chromatography. 15 (12): 785–790. doi:10.1002/jhrc.1240151203.
^ Hušek, Petr (1998). "Chloroformates in gas chromatography as general purpose derivatizing agents". Journal of Chromatography B: Biomedical Sciences and Applications. 717 (1–2): 57–91. doi:10.1016/S0378-4347(98)00136-4. PMID 9832240.

[1] "Safety data sheet: 2-chloroethyl chloroformate". Sigmaaldrich.com. Retrieved 2025-06-30.

[2] Jones, J. Idris (1957). "530. The reaction of carbonyl chloride with 1 : 2-epoxides". Journal of the Chemical Society (Resumed): 2735. doi:10.1039/JR9570002735.

[3] Mousseau, James J. (2011). "β-Chloroethyl Chloroformate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01309. ISBN 978-0-471-93623-7.

[4] Wu, Yikang; Shen, Xin (2000). "A high-yielding low-cost facile synthesis of 2-oxazolidinones chiral auxiliaries". Tetrahedron: Asymmetry. 11 (21): 4359–4363. doi:10.1016/S0957-4166(00)00415-8.

[5] Vreeken, Rob J.; Jager, Maria E.; Ghijsen, Rudy T.; Brinkman, Udo A. Th. (1992). "The derivatization of fatty acids by (Chloro)alkyl chloroformates in non-aqueous and aqueous media for GC analysis". Journal of High Resolution Chromatography. 15 (12): 785–790. doi:10.1002/jhrc.1240151203.

[6] Hušek, Petr (1998). "Chloroformates in gas chromatography as general purpose derivatizing agents". Journal of Chromatography B: Biomedical Sciences and Applications. 717 (1–2): 57–91. doi:10.1016/S0378-4347(98)00136-4. PMID 9832240.

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