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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:
131208
EC Number:
208-358-1
MDL number:
MFCD00005891
UNSPSC Code:
12352005
PubChem Substance ID:
24895686
NACRES:
NA.22
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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.[1]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF5430V
WXBF1430V
WXBD8210V
WXBD3562V
WXBD2011V

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Tetrahedron Letters, 33, 2645-2645 (1992)
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
Francesca D'Acunzo et al.
European journal of biochemistry, 269(21), 5330-5335 (2002-10-24)
To investigate how solubility and steric issues affect the laccase-catalysed oxidation of phenols, a series of oligomeric polyphenol compounds, having increasing size and decreasing solubility in water, was incubated with laccase. The extent of substrate conversion, and the nature of
Yuuki Amaoka et al.
The Journal of organic chemistry, 77(22), 9959-9969 (2012-11-02)
A direct conversion of C(sp(3))-H bonds to C(sp(3))-N bonds has been achieved by utilizing catalytic N-hydroxyphthalimide (NHPI) and stoichiometric dialkyl azodicarboxylate. NHPI functions as a precursor of the electron-deficient phthalimide N-oxyl radical (PINO) to abstract hydrogens, and dialkyl azodicarboxylate acts
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)
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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