Isobutyryl chloride

Isobutyryl chloride (2-methylpropanoyl chloride) is the organic compound with the formula (CH₃)₂CHCOCl. A colorless liquid, it the simplest branched-chain acyl chloride. It is prepared by chlorination of isobutyric acid.^[2]

Isobutyryl chloride

Names
Preferred IUPAC name 2-Methylpropanoyl chloride
Other names Isobutyroyl chloride
Identifiers
CAS Number	79-30-1
3D model (JSmol)	Interactive image
ChemSpider	56120
ECHA InfoCard	100.001.086
PubChem CID	62325
UNII	6617F0VJZC
CompTox Dashboard (EPA)	DTXSID0052542
InChI InChI=1S/C4H7ClO/c1-3(2)4(5)6/h3H,1-2H3 Key: DGMOBVGABMBZSB-UHFFFAOYSA-N
SMILES CC(C)C(=O)Cl
Properties
Chemical formula	C4H7ClO
Molar mass	106.55 g·mol−1
Density	1.017 g/mL[1]
Melting point	−90 °C[1]
Boiling point	91–93 °C (196–199 °F; 364–366 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Reactions

As an ordinary acid chloride, isobutyryl chloride is the subject of many reported transformations. Dehydrohalogenation of isobutyryl chloride with triethylamine gives 2,2,4,4-tetramethylcyclobutanedione.^[3] Treatment of isobutyryl chloride with hydrogen fluoride gives the acid fluoride.^[4]

References

1. "Isobutyryl chloride". Sigma-Aldrich.
2. Kent, R. E.; McElvain, S. M. (1945). "Isobutyramide". Organic Syntheses. 25: 58. doi:10.15227/orgsyn.025.0058.
3. R. Huisgen, P. Otto (1968), "The mechanism of dimerization of dimethylketene", J. Am. Chem. Soc., vol. 90, no. 19, pp. 5342–5343, doi:10.1021/ja01021a090
4. Olah, George A.; Kuhn, Stephen J. (1965). "Benzoyl Fluoride". Organic Syntheses. 45: 3. doi:10.15227/orgsyn.045.0003.