4838. N-Hydroxyphthalimide

Nomenclature

CAS number: 524-38-9
2-Hydroxy-1H-isoindole-1,3(2H)-dione; NHPI.
C8H5NO3; mol wt 163.13.
C 58.90%, H 3.09%, N 8.59%, O 29.42%.

Description and references

Mediates oxidative catalytic transformations of organic compounds with molecular oxygen. Prepn: L. Cohn, Ann. 205, 295 (1880); H. Gross, I. Keitel, J. Prakt. Chem. 311, 692 (1969). Crystal structure: F.-M. Miao et al., Acta Crystallogr. C51, 712 (1995). Transition metal free oxidation reactions: C. Einhorn et al., Chem. Commun. 1997, 447; epoxidation of alkenes: T. Iwahama et al., Heterocycles 52, 693 (2000). Transition metal cocatalysis in alkane oxidation: Y. Ishii et al., J. Org. Chem. 61, 4520 (1996); in hydroxylation of fatty acids: M. A. Oakley et al., J. Mol. Catal. A 150, 105 (1999). Description of catalytic mechanisms: Y. Ishii, S. Sakaguchi, Catal. Surv. Jpn. 3, 27 (1999).

Chemical structure

Properties

Yellowish needles from water, mp 227-229°. Also reported as colorless monoclinic crystals from water. d 1.59 mg m3.

Use

Catalyst for oxidation reactions.