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, decomposing into carbon dioxide and hydrogen chloride.^[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