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Chloroformic acid

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Chloroformic acid
Structural formula of chloroformic acid
Space-filling model of the chloroformic acid molecule
Names
Preferred IUPAC name Carbonochloridic acid
Other names Chloroformic acid
Chlorocarbonic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
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
Acidity (pKa) 0.27
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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. 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

References

  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.
  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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