Chloroformic acid is a chemical compound with the formula ClCO2H. 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]
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| Names | |||
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| Preferred IUPAC name
Carbonochloridic acid[1] | |||
| Other names
Chloroformic acid
Chlorocarbonic acid | |||
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| Properties | |||
| ClCO2H | |||
| Molar mass | 80.47 g·mol−1 | ||
| Acidity (pKa) | 0.27[2] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.
See also
editReferences
edit- ^ 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.