Chloroformic acid

Chloroformic acid
IUPAC name Carbonochloridic acid
Other names Chlorocarbonic acid
Identifiers
CAS number	463-73-0
PubChem	164602
ChemSpider	144299 Y
Jmol-3D images	Image 1
SMILES ClC(=O)O
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
Properties
Molecular formula	CHClO2
Molar mass	80.47 g mol−1
Y acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

• Chloroacetic acids
• Dichloroacetic acid
• Trichloroacetic acid

References

• "Chloroformic acid; Chlorocarbonic acid; Carbonochloridic acid". Dow Chemical. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=742051. Retrieved 20 May 2007. 
• "Monochloroacetic Acid". IPCS Inchem. http://www.inchem.org/documents/pims/chemical/pim352.htm. Retrieved 20 May 2007.