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N-Hydroxyphthalimide

CAS No.:
524-38-9
Catalog Number:
AG0035DW
Molecular Formula:
C8H5NO3
Molecular Weight:
163.1302
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5g
95%
In Stock USA
United States
$13
- +
25g
95%
In Stock USA
United States
$17
- +
100g
98%
In Stock USA
United States
$50
- +
250g
98%(HPLC)
In Stock USA
United States
$104
- +
500g
98%(HPLC)
In Stock USA
United States
$186
- +
Product Description
Catalog Number:
AG0035DW
Chemical Name:
N-Hydroxyphthalimide
CAS Number:
524-38-9
Molecular Formula:
C8H5NO3
Molecular Weight:
163.1302
MDL Number:
MFCD00005891
IUPAC Name:
2-hydroxyisoindole-1,3-dione
InChI:
InChI=1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)8(11)9(7)12/h1-4,12H
InChI Key:
CFMZSMGAMPBRBE-UHFFFAOYSA-N
SMILES:
ON1C(=O)c2c(C1=O)cccc2
EC Number:
208-358-1
UNII:
BXI99M81X0
NSC Number:
770
Properties
Complexity:
215  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
163.027g/mol
Formal Charge:
0
Heavy Atom Count:
12  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
163.132g/mol
Monoisotopic Mass:
163.027g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
57.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.8  
Literature
Title Journal
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Atmospheric-pressure, liquid-phase, selective aerobic oxidation of alkanes catalysed by metal-organic frameworks. Chemistry (Weinheim an der Bergstrasse, Germany) 20110523
Neurosteroid dehydroepiandrosterone interacts with nerve growth factor (NGF) receptors, preventing neuronal apoptosis. PLoS biology 20110401
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A metal-free aerobic oxidation of nitrotoluenes catalyzed by N,N',N″-trihydroxyisocyanuric acid (THICA) and a novel approach to the catalyst. Journal of hazardous materials 20101215
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Novel convenient synthesis of biologically active esters of hydroxylamine. Amino acids 20100201
Reactivity and applications of new amine reactive cross-linkers for mass spectrometric detection of protein-protein complexes. Analytical chemistry 20100101
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Electron-transfer properties of short-lived N-oxyl radicals. Kinetic study of the reactions of benzotriazole-N-oxyl radicals with ferrocenes. Comparison with the phthalimide-N-oxyl radical. The Journal of organic chemistry 20090807
The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine: a chiral Weinreb amide equivalent. Organic letters 20090806
Anthrone-derived NHPI analogues as catalysts in reactions using oxygen as an oxidant. Organic & biomolecular chemistry 20081121
Crystal growth and characterization of N-hydroxyphthalimide (C8H5NO3) crystal. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20081101
Cu-facilitated C-O bond formation using N-hydroxyphthalimide: efficient and selective functionalization of benzyl and allylic C-H bonds. Journal of the American Chemical Society 20080625
Pronounced non-Arrhenius behaviour of hydrogen-abstractions from toluene and derivatives by phthalimide-N-oxyl radicals: a theoretical study. Physical chemistry chemical physics : PCCP 20080227
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Engineering and Applications of fungal laccases for organic synthesis. Microbial cell factories 20080101
N-hydroxyimides as efficient ligands for the copper-catalyzed N-arylation of pyrrole, imidazole, and indole. The Journal of organic chemistry 20071109
A kinetic study of the electron-transfer reaction of the phthalimide-N-oxyl radical (PINO) with ferrocenes. The Journal of organic chemistry 20071109
Free radical functionalization of organic compounds catalyzed by N-hydroxyphthalimide. Chemical reviews 20070901
Alpha and beta L-Fucopyranosyl oxyamines: key intermediates for the preparation of fucose-containing glycoconjugates by oxime ligation. Carbohydrate research 20070521
Elusive forms and structures of N-hydroxyphthalimide: the colorless and yellow crystal forms of N-hydroxyphthalimide. The journal of physical chemistry. A 20070405
Variable C2-symmetric analogues of N-hydroxyphthalimide as enantioselective catalysts for aerobic oxidation: kinetic resolution of oxazolidines. Angewandte Chemie (International ed. in English) 20070101
Occupational contact dermatitis (drug-induced medicamentosa): six case reports. International journal of immunopathology and pharmacology 20070101
One-pot synthesis of lactams from cycloalkanes and tert-butyl nitrite by using N-hydroxyphthalimide as key catalyst. Chemistry, an Asian journal 20061120
[Hydroxyphthalimide induced medicamentosa-like dermatitis in five patients]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases 20061001
Kinetic study of the hydrogen abstraction reaction of the benzotriazole-N-oxyl radical (BTNO) with H-donor substrates. The Journal of organic chemistry 20051111
A new supported reagent for the parallel synthesis of primary and secondary O-alkyl hydroxylamines through a base-catalyzed Mitsunobu reaction. The Journal of organic chemistry 20050805
Electron-transfer mechanism in the N-demethylation of N,N-dimethylanilines by the phthalimide-N-oxyl radical. The Journal of organic chemistry 20050624
Mechanisms of reaction of aminoxyl (nitroxide), iminoxyl, and imidoxyl radicals with alkenes and evidence that in the presence of lead tetraacetate, N-hydroxyphthalimide reacts with alkenes by both radical and nonradical mechanisms. The Journal of organic chemistry 20050610
Selective organocatalytic oxygenation of hydrocarbons by dioxygen using anthraquinones and N-hydroxyphthalimide. Organic letters 20050120
Kinetics of self-decomposition and hydrogen atom transfer reactions of substituted phthalimide N-oxyl radicals in acetic acid. The Journal of organic chemistry 20050107
Application of a dual linker with a reference cleavage site to discover a new reaction between amines and N-hydroxyphthalimide. Journal of combinatorial chemistry 20050101
Reactivity of phthalimide N-oxyl radical (PINO) toward the phenolic O-H bond. A kinetic study. The Journal of organic chemistry 20041210
Biomimetic catalytic system driven by electron transfer for selective oxygenation of hydrocarbon. Journal of the American Chemical Society 20040901
Novel method for efficient aerobic oxidation of silyl ethers to carbonyl compounds catalyzed with N-hydroxyphthalimide (NHPI) and lipophilic Co(II) complexes. Organic letters 20040819
Mechanism of the catalytic oxidation of hydrocarbons by N-hydroxyphthalimide: a theoretical study. Chemical communications (Cambridge, England) 20040507
A new route to lactam precursors from cycloalkanes: direct production of nitrosocycloalkanes or cycloalkanone oximes by using tert-butyl nitrite and N-hydroxyphthalimide. Angewandte Chemie (International ed. in English) 20040220
New efficient aerobic oxidation of some alcohols with dioxygen catalysed by N-hydroxyphtalimide with vanadium co-catalysts. Chemical communications (Cambridge, England) 20040121
Kinetic study of the phthalimide N-oxyl radical in acetic acid. Hydrogen abstraction from substituted toluenes, benzaldehydes, and benzyl alcohols. The Journal of organic chemistry 20031128
Controlling mode selectivity in palladium-catalyzed bisdiene carbocyclizations: optimizing for cyclization-trapping over cycloisomerization. Organic letters 20031002
Oxidation of substituted toluenes with molecular oxygen in the presence of N,N',N' '-trihydroxyisocyanuric acid as a key catalyst. The Journal of organic chemistry 20030822
Use of a pharmacophore model to discover a new class of influenza endonuclease inhibitors. Journal of medicinal chemistry 20030327
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Synthesis of a new heterobifunctional linker, N-[4-(aminooxy)butyl]maleimide, for facile access to a thiol-reactive 18F-labeling agent. Bioconjugate chemistry 20030101
Oxidation of phenols by laccase and laccase-mediator systems. European journal of biochemistry 20021101
An efficient nitration of light alkanes and the alkyl side-chain of aromatic compounds with nitrogen dioxide and nitric acid catalyzed by N-hydroxyphthalimide. The Journal of organic chemistry 20020809
Aerobic oxidation of N-alkylamides catalyzed by N-hydroxyphthalimide under mild conditions. Polar and enthalpic effects. The Journal of organic chemistry 20020419
A new, highly selective synthesis of aromatic aldehydes by aerobic free-radical oxidation of benzylic alcohols, catalysed by n-hydroxyphthalimide under mild conditions. Polar and enthalpic effects. Chemical communications (Cambridge, England) 20020407
First Ritter-type reaction of alkylbenzenes using N-hydroxyphthalimide as a key catalyst. Chemical communications (Cambridge, England) 20020307
The radical-chain addition of aldehydes to alkenes by the use of N-hydroxyphthalimide (NHPI) as a polarity-reversal catalyst. Chemical communications (Cambridge, England) 20011121
Catalytic oxyalkylation of alkenes with alkanes and molecular oxygen via a radical process using N-hydroxyphthalimide. The Journal of organic chemistry 20010921
The copper-mediated cross-coupling of phenylboronic acids and N-hydroxyphthalimide at room temperature: synthesis of aryloxyamines. Organic letters 20010111
Properties