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N-Hydroxyphthalimide

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N-Hydroxyphthalimide Basic information

Product Name:
N-Hydroxyphthalimide
Synonyms:
  • TIMTEC-BB SBB009098
  • N-HYDROXY-PHTALIMIDE
  • N-HYDROXYPHTHALIMIDE
  • 2-hydroxy-1h-isoindole-3(2h)-dione
  • N-Hydroxyphthalimide, remainder 10-15% moisture
  • N-Hydroxyphehtalimide
  • N-HYDROXYMETHYL-3-METHYLOXETANE
  • N-Hydroxyphthalimide(Nop)
CAS:
524-38-9
MF:
C8H5NO3
MW:
163.13
EINECS:
208-358-1
Product Categories:
  • Active Esters/Additives
  • Active Esters/AdditivesSynthetic Reagents
  • Biochemistry
  • Carbon Radical Producing Catalysts (Environmentally-friendly Oxidation)
  • Coupling
  • Peptide Synthesis
  • Condensation & Active Esterification
  • Coupling Reactions (Peptide Synthesis)
  • Environmentally-friendly Oxidation
  • N-Substituted Maleimides, Succinimides & Phthalimides
  • N-Substituted Phthalimides
  • Peptide Synthesis
  • Synthetic Organic Chemistry
  • API
  • intermediates
  • bc0001
  • 524-38-9
Mol File:
524-38-9.mol
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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)
form 
Powder
pka
6.10±0.20(Predicted)
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)
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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

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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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