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[1]
Other names
Chloroformic acid
Chlorocarbonic acid
Identifiers
3D model (
JSmol
)
ChemSpider
  • InChI=1S/CHClO2/c2-1(3)4/h(H,3,4) checkY
    Key: AOGYCOYQMAVAFD-UHFFFAOYSA-N checkY
  • InChI=1/CHClO2/c2-1(3)4/h(H,3,4)
    Key: AOGYCOYQMAVAFD-UHFFFAOYAQ
  • ClC(=O)O
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).
checkY verify (what is checkY☒N ?)

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]

Chloroformic acid itself is too unstable to be handled for chemical reactions. However, many

carboxylic acid anhydrides used in peptide synthesis
. Important chloroformate esters include
fluorenylmethyloxycarbonylchloride, benzyl chloroformate and ethyl chloroformate
.

See also

References

  1. 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. doi:10.1021/cr60261a005
    .
  4. doi:10.1021/cr60232a004
    .
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