Isobutyric anhydride

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Isobutyric anhydride
Isobutyric anhydride v2.svg
Names
IUPAC name
2-Methylpropanoic anhydride
Other names
  • Isobutyric acid anhydride
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.367 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-603-6
PubChem CID
UNII
UN number 2924 2530
  • InChI=1S/C8H14O3/c1-5(2)7(9)11-8(10)6(3)4/h5-6H,1-4H3
    Key: LSACYLWPPQLVSM-UHFFFAOYSA-N
  • CC(C)C(=O)OC(=O)C(C)C
Properties
C8H14O3
Molar mass 158.197 g·mol−1
AppearanceColorless liquid [1]
Density 0.9535 g/cm³ (at 20 °C)
Melting point −53.5 °C (−64.3 °F; 219.7 K)
Boiling point 181.5 °C (358.7 °F; 454.6 K)
Vapor pressure 0.5 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Isobutyric anhydride is an organic compound with the formula ((CH3)2CHCO)2O. It is an acyclic carboxylic anhydride of isobutyric acid. [2] It is classified as an organic acid anhydride, being derived from dehydration of isobutyric acid. It is a colorless liquid with a strong, pungent odor. [1] [3]

Isobutyric anhydride is a reagent in the production of the ester of cyclohexanone oxime. [4]

Applications

Isobutyric anhydride is used as an acylating agent in organic synthesis. Its primary application is in the production of esters, such as cyclohexanone oxime. [4] Isobutyric anhydride is used in the synthesis of various dyes. [5] It is also used in the production of cellulose derivatives, such as cellulose isobutyrate and cellulose acetate isobutyrate. [6] [7] Another application of isobutyric anhydride is in the synthesis of various chemical derivatives. For example, it is used to produce 4-O-isobutyryl derivatives of monosaccharides. [8]

References

  1. 1 2 "Isobutyric Anhydride" . Retrieved March 21, 2025.
  2. ↑ "Isobutyric acid anhydride (CHEBI:84261)".
  3. ↑ "Product Description and Handling Guide - Isobutyric Anhydride" (PDF). Celanese .
  4. 1 2 Dikusar, E. A.; Zhukovskaya, N. A. (2008). "Preparative synthesis of cyclohexanone oxime esters". Russian Journal of Organic Chemistry. 44 (9): 1389–1391. doi:10.1134/s1070428008090248.
  5. ↑ "Isobutyric Anhydride | 97-72-3 | Chemical Bull PVT. LTD".
  6. ↑ Larionov, Evgeny; Mahesh, Mohan; Spivey, Alan C.; Wei, Yin; Zipse, Hendrik (2012). "Theoretical Prediction of Selectivity in Kinetic Resolution of Secondary Alcohols Catalyzed by Chiral DMAP Derivatives" . Journal of the American Chemical Society. 134 (22): 9390–9399. Bibcode:2012JAChS.134.9390L. doi:10.1021/ja302420g. hdl: 10044/1/15222 . PMID   22568686.
  7. ↑ Seddiqi, Hadi; Oliaei, Erfan; Honarkar, Hengameh; Jin, Jianfeng; Geonzon, Lester C.; Bacabac, Rommel G.; Klein-Nulend, Jenneke (2021). "Cellulose and its derivatives: Towards biomedical applications". Cellulose. 28 (4): 1893–1931. doi: 10.1007/s10570-020-03674-w .
  8. ↑ Kawabata, Takeo; Muramatsu, Wataru; Nishio, Tadashi; Shibata, Takeshi; Schedel, Hartmut (2007). "A Catalytic One-Step Process for the Chemo- and Regioselective Acylation of Monosaccharides" . Journal of the American Chemical Society. 129 (42): 12890–12895. Bibcode:2007JAChS.12912890K. doi:10.1021/ja074882e. PMID   17902666.
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