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H53704

Sigma-Aldrich

N-Hydroxyphthalimide

97%, for peptide synthesis

Synonym(s):

2-Hydroxy-1H-isoindole-1,3(2H)-dione, 2-Hydroxyisoindole-1,3-dione, 2-Hydroxyphthalimide

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About This Item

Empirical Formula (Hill Notation):
C8H5NO3
CAS Number:
524-38-9
Molecular Weight:
163.13
Beilstein/REAXYS Number:
131208
EC Number:
208-358-1
MDL number:
MFCD00005891
UNSPSC Code:
12352005
PubChem Substance ID:
24895686
NACRES:
NA.22

product name

N-Hydroxyphthalimide, 97%

assay

97%

form

crystalline

reaction suitability

reaction type: Addition Reactions

mp

233 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

ON1C(=O)c2ccccc2C1=O

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

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Application

For preparation of amine nucleosides for coupling into non-anionic, anti-sense oligonucleosides.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD3562V
WXBD2011V
MKCL7821
MKCJ1270
MKCJ1238

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Tetrahedron Letters, 33, 2645-2645 (1992)
Application of a dual linker with a reference cleavage site to discover a new reaction between amines and N-hydroxyphthalimide.
Viktor Krchnák et al.
Journal of combinatorial chemistry, 7(4), 523-525 (2005-07-12)
Guanyu Yang et al.
Journal of the American Chemical Society, 126(34), 10542-10543 (2004-08-26)
Hydrocarbon oxyfunctionalization is a crucial industrial process. Most metallic catalysts require higher temperatures and often show lower selectivities. One of the intellectual approaches is the mimicry for bio-oxidation. We have established a biomimetic system with a nonmetallic redox center, composed
Markus Tonigold et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(31), 8671-8695 (2011-06-21)
Crystal structures of two metal-organic frameworks (MFU-1 and MFU-2) are presented, both of which contain redox-active Co(II) centres coordinated by linear 1,4-bis[(3,5-dimethyl)pyrazol-4-yl] ligands. In contrast to many MOFs reported previously, these compounds show excellent stability against hydrolytic decomposition. Catalytic turnover
Riyuan Lin et al.
Organic letters, 14(16), 4158-4161 (2012-08-03)
A metal-free N-hydroxyphthalimide (NHPI) catalyzed aerobic oxidative cleavage of olefins has been developed. Molecular oxygen is used as the oxidant and reagent for this oxygenation reaction. This methodology has prevented the use of toxic metals or overstoichiometric amounts of traditional
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