Isobutyryl chloride

Last updated
Isobutyryl chloride
Isobutyryl chloride.svg
Names
Preferred IUPAC name
2-Methylpropanoyl chloride
Other names
Isobutyroyl chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.086 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C4H7ClO/c1-3(2)4(5)6/h3H,1-2H3
    Key: DGMOBVGABMBZSB-UHFFFAOYSA-N
  • CC(C)C(=O)Cl
Properties
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).

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]

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. 1 2 3 "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, Bibcode:1968JAChS..90.5342H, doi:10.1021/ja01021a090
  4. ↑ Olah, George A.; Kuhn, Stephen J. (1965). "Benzoyl Fluoride". Organic Syntheses. 45: 3. doi:10.15227/orgsyn.045.0003.
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