Chloroformic acid

Names

Preferred IUPAC name

Carbonochloridic acid

Other names

Chloroformic acid (no longer recommended)
Chlorocarbonic acid

Identifiers

CAS Number

463-73-0^Y

3D model (JSmol)

Interactive image

ChemSpider

144299^Y

PubChem CID

164602

InChI

InChI=1S/CHClO2/c2-1(3)4/h(H,3,4)^Y

Key: AOGYCOYQMAVAFD-UHFFFAOYSA-N^Y
InChI=1/CHClO2/c2-1(3)4/h(H,3,4)

Key: AOGYCOYQMAVAFD-UHFFFAOYAQ

SMILES

ClC(=O)O

Properties

Chemical formula

CHClO₂

Molar mass

80.47 g·mol⁻¹

Density

1.576

Refractive index (n_D)

1.426

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^Y ?)

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.

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