Isobutyric anhydride

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

Names
IUPAC name 2-Methylpropanoic anhydride
Other names Isobutyric acid anhydride
Identifiers
CAS Number	97-72-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:84261
ChEMBL	ChEMBL1871691
ChemSpider	7069
ECHA InfoCard	100.002.367
EC Number	202-603-6
PubChem CID	7346
UNII	N85A80FJDT
UN number	2924 2530
CompTox Dashboard (EPA)	DTXSID7026609
InChI InChI=1S/C8H14O3/c1-5(2)7(9)11-8(10)6(3)4/h5-6H,1-4H3 Key: LSACYLWPPQLVSM-UHFFFAOYSA-N
SMILES CC(C)C(=O)OC(=O)C(C)C
Properties
Chemical formula	C8H14O3
Molar mass	158.197 g·mol−1
Appearance	Colorless 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). Infobox references

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]