N-Hydroxyphthalimide Chemical Properties

Melting point:

233 °C (dec.) (lit.)

Boiling point:

290.19°C (rough estimate)

Density 

1.64 g/cm3

vapor pressure 

0Pa at 25℃

refractive index 

1.5510 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

6.10±0.20(Predicted)

form 

Powder

color 

Yellow

Water Solubility 

Slightly soluble in water.

Merck 

14,4838

BRN 

131208

InChIKey

CFMZSMGAMPBRBE-UHFFFAOYSA-N

LogP

0.14

CAS DataBase Reference

524-38-9(CAS DataBase Reference)

EPA Substance Registry System

1H-Isoindole-1,3(2H)-dione, 2-hydroxy- (524-38-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

TI5200000

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29251995

MSDS

• Language:English Provider:N-Hydroxyphthalimide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

N-Hydroxyphthalimide Usage And Synthesis

Chemical Properties

N-Hydroxyphthalimide is yellow moist powder

Uses

Catalyst for oxidation reactions.

Uses

N-Hydroxyphthalimide，additives in to DCC method of peptide synthesis used to improve yield of optically pure product.

Uses

Aerobic oxidation of various alcohols has been accomplished by using a new catalytic system, N-hydroxyphthalimide (NHPI) combined with Co (acac). A practical catalytic method to convert alkylbenzenes into the corresponding carboxylic acids under atmospheric dioxygen at ambient temperature using a combined catalytic system consisting of N-hydroxyphthalimide (NHPI) and Co (OAc) 2 was developed. Novel catalysis by N-hydroxyphthalimide in the oxidation of organic substrates by molecular oxygen was described. Free radical functionalization of organic compounds catalyzed by N-hydroxyphthalimide. Purely organic and catalytic systems of anthraquinones and N-hydroxyphthalimide efficiently promote oxygenation of hydrocarbons with dioxygen under mild conditions. Hydroxylation of polycyclic alkanes with molecular oxygen catalyzed by N-hydroxyphthalimide (NHPI) combined with was transition metal salts.

Application

N-Hydroxyphthalimide is used in the synthesis of a new class of antibacterials potent against macrolide resistant bacteria. Also used in the synthesis of pyrazolidines, isoxazolidines and tetrahydrooxazines.

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 2035, 1996 DOI: 10.1016/0040-4039(96)00211-0

Purification Methods

N -Hydroxyphthalimide [524-38-9] M 163.1, m 230o, ~235o(dec), 237-240o, 7.0. Dissolve the imide in H2O by adding Et3N to form the salt and while hot, acidify, cool and pour into a large volume of H2O. Filter off the solid, wash it with H2O and dry it over P2O5 in a vacuum. [Nefken & Teser J Am Chem Soc 83 1263 1961, Fieser 1 485 1976, Nefkens et al. Recl Trav Chim, Pays-Bas 81 683 1962] The O-acetyl derivative has m 178-180o (from EtOH). [Beilstein 21/11 V 100.]

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