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 (no longer recommended[1])
Chlorocarbonic acid
Identifiers
463-73-0 YesY
3D model (Jmol) Interactive image
ChemSpider 144299 YesY
PubChem 164602
Properties
CHClO2
Molar mass 80.47 g·mol−1
Density 1.576
1.426
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Chloroformic acid is an unstable 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, which has a hydrogen instead of the chlorine. Despite the similar name, it is very different from chloroform.

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. Like other related halocarbons, it is a potentially dangerous alkylating agent.

Important chloroformate esters include 4-nitrophenyl chloroformate, fluorenylmethyloxycarbonylchloride, benzyl chloroformate and ethyl chloroformate.

See also[edit]

References[edit]

  1. ^ a b 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.