Chemistry:Isobutyryl chloride

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Isobutyryl chloride
Isobutyryl chloride.svg
Names
Preferred IUPAC name
2-Methylpropanoyl chloride
Other names
Isobutyroyl chloride
Identifiers
3D model (JSmol)
ChemSpider
UNII
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).
Infobox references
Tracking categories (test):

Isobutyryl chloride (2-methylpropanoyl chloride) is the organic compound with the formula (CH
3
)
2
CHCOCl
. 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. 1.0 1.1 1.2 "Isobutyryl chloride". Sigma-Aldrich. https://www.sigmaaldrich.com/catalog/product/aldrich/139122?lang=en. 
  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. 90 (19): 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.