Chloroformic acid

Chloroformic acid
Names
	Preferred IUPAC name Carbonochloridic acid
	Other names Chloroformic acid; Chlorocarbonic acid
Identifiers
CAS Number	463-73-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	144299 ;
PubChem CID	164602;
CompTox Dashboard (EPA)	DTXSID10196802 ;
	InChI InChI=1S/CHClO2/c2-1(3)4/h(H,3,4) Key: AOGYCOYQMAVAFD-UHFFFAOYSA-N ; InChI=1/CHClO2/c2-1(3)4/h(H,3,4) Key: AOGYCOYQMAVAFD-UHFFFAOYAQ;
	SMILES ClC(=O)O;
Properties
Chemical formula	ClCO2H
Molar mass	80.47 g·mol−1
Acidity (pKa)	0.27
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Chloroformic acid is a chemical compound with the formula Cl C O₂H. It is the single acyl-halide derivative of carbonic acid (phosgene is the double acyl-halide derivative). Chloroformic acid is also structurally related to formic acid, in a way that the non-acidic hydrogen of formic acid is replaced by chlorine. Despite the similar name, it is very different from chloroform. It is described as unstable.^[3]

Chloroformic acid itself is too unstable to be handled for chemical reactions. However, many esters of this carboxylic acid are stable and these chloroformates are important reagents in organic chemistry.^[4] They are used to prepare mixed carboxylic acid anhydrides used in peptide synthesis. Important chloroformate esters include 4-nitrophenyl chloroformate, fluorenylmethyloxycarbonylchloride, benzyl chloroformate and ethyl chloroformate.

References

^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 776–777. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ "Archived copy". Archived from the original on 2023-12-10. Retrieved 2023-12-30.{{cite web}}: CS1 maint: archived copy as title (link)
^ Gibson, Harry W. (1969). "Chemistry of Formic Acid and Its Simple Derivatives". Chemical Reviews. 69 (5): 673–692. doi:10.1021/cr60261a005.
^ Matzner, Markus; Kurkjy, Raymond P.; Cotter, Robert J. (1964). "The Chemistry of Chloroformates". Chemical Reviews. 64 (6): 645–687. doi:10.1021/cr60232a004.

[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 776–777. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[metabolites-2] "Archived copy". Archived from the original on 2023-12-10. Retrieved 2023-12-30.{{cite web}}: CS1 maint: archived copy as title (link)

[3] Gibson, Harry W. (1969). "Chemistry of Formic Acid and Its Simple Derivatives". Chemical Reviews. 69 (5): 673–692. doi:10.1021/cr60261a005.

[4] Matzner, Markus; Kurkjy, Raymond P.; Cotter, Robert J. (1964). "The Chemistry of Chloroformates". Chemical Reviews. 64 (6): 645–687. doi:10.1021/cr60232a004.

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See also

References