Carbon oxohalide


Carbon oxohalides are a group of chemical compounds that contain only carbon, oxygen and halogen atoms: fluorine, chlorine, bromine and iodine. They include carbonyl halides,, and oxalyl halides,, where X = F, Cl, Br or I. The halogen atoms X do not have to be identical; they differ in mixed oxohalides. Most combinations of halogens exist but carbonyl iodide,, is unknown. The carbon–oxygen bond length in carbonyl halides is shorter than in other carbonyl compounds such as aldehydes and ketones, carboxylic acids, esters and amides. They are reactive reagents for halogenation, acylation and dehydration reactions.
NameFormulaMelting point / °CBoiling point / °CC–O bond length / Å
Carbonyl fluoride−114−83.11.174
Carbonyl chloride fluorideCOFCl−42
Carbonyl bromide fluorideCOFBr−20.6
Phosgene−127.8+7.61.166
Carbonyl iodide fluorideCOFI−90+23.4
Carbonyl bromide chlorideCOClBr
Carbonyl bromide+64.51.13
Oxalyl fluoride−3+26.6
Oxalyl chloride−16+63
Diphosgene−57+128
Triphosgene+80+206