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.[3][4]
| |
| Names | |
|---|---|
| IUPAC name
2-Methylpropanoyl 2-methylpropanoate
| |
Other names
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.002.367 |
| EC Number |
|
PubChem CID
|
|
| UNII | |
| UN number | 2924 2530 |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C8H14O3 | |
| Molar mass | 158.197 g·mol−1 |
| Appearance | Colorless liquid [1] |
| Density | 0.9535 g/cm³, l @ 20 °C/4 °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 a reagent in the production of the ester of cyclohexanone oxime.[5]
Applications
editIsobutyric anhydride is used as an acylating agent in organic synthesis. Its primary application is in the production of esters, such as cyclohexanone oxime.[5] Isobutyric anhydride is used in the synthesis of various dyes.[6] It is also used in the production of cellulose derivatives, such as cellulose isobutyrate and cellulose acetate isobutyrate.[7][8] 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.[9]
References
edit- ^ "ISOBUTYRIC ANHYDRIDE | CAMEO Chemicals | NOAA".
- ^ "Isobutyric acid anhydride (CHEBI:84261)".
- ^ "Product Description and Handling Guide - Isobutyric Anhydride" (PDF). Celanese.
- ^ "ISOBUTYRIC ANHYDRIDE | CAMEO Chemicals | NOAA".
- ^ a b 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.
- ^ "Isobutyric Anhydride | 97-72-3 | Chemical Bull PVT. LTD".
- ^ 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. doi:10.1021/ja302420g. hdl:10044/1/15222. PMID 22568686.
- ^ 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.
- ^ 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. doi:10.1021/ja074882e. PMID 17902666.