N-Hydroxyphthalimide

N-Hydroxyphthalimide
Names
Preferred IUPAC name
2-Hydroxy-1H-isoindole-1,3(2H)-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.600 Edit this at Wikidata
EC Number
  • 208-358-1
UNII
  • InChI=1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)8(11)9(7)12/h1-4,12H
    Key: CFMZSMGAMPBRBE-UHFFFAOYSA-N
  • O=C2N(O)C(C1=CC=CC=C12)=O
Properties
C8H5NO3
Molar mass 163.132 g·mol−1
Appearance white to pale yellow crystalline solid
Density 1.64 g/mL
Melting point 233°C
Boiling point 370°C
water, polar organic solvents
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N-Hydroxyphthalimide is the organic compound with the formula C6H4(CO)2NOH. A white or yellow solid, it is a derivative of phthalimide. The compound is as a catalyst in the synthesis of other organic compounds.[1][2] It is soluble in water and organic solvents such as acetic acid, ethyl acetate and acetonitrile.[3]

  1. ^ Recupero, Francesco; Punta, Carlo (2007). "Free Radical Functionalization of Organic Compounds Catalyzed by N-Hydroxyphthalimide". Chem. Rev. 107 (9): 3800–3842. doi:10.1021/cr040170k. PMID 17848093.
  2. ^ Melone, Lucio; Punta, Carlo (2013). "Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review". Beilstein J. Org. Chem. 9: 1296–1310. doi:10.3762/bjoc.9.146. PMC 3701383. PMID 23843925.
  3. ^ Gambarotti, Cristian; Punta, Carlo; Recupero, Francesco; Zlotorzynska, Maria; Sammis, Glenn (2013). "N-Hydroxyphthalimide". N-Hydrophthalimide. Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00598.pub2. ISBN 978-0471936237.