CAS 524-38-9|N-hydroxyphthalimide|2-Hydroxy-1H-isoindole-1,3(2H)-dione|2-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione|2-hydroxyisoindoline-1,3-dione|2-Hydroxyisoindolin-1,3-dione|N-Hydroxyphthalimide|...

General Information

Structure

Molecular Formula

C₈H₅NO₃

Molecular Mass

163.1302

Exact Mass

163.02694303

Charge

InChI

InChI=1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)8(11)9(7)12/h1-4,12H

InChIKey

CFMZSMGAMPBRBE-UHFFFAOYSA-N

Canonic Smiles

ON1C(=O)c2c(C1=O)cccc2

Isomeric Smiles

N1(C(=O)c2c(C1=O)cccc2)O

Calculated Properties

JChem

Acid pKa

7.4305606

H Acceptors

H Donor

LogD (pH = 5.5)

0.68519646

LogD (pH = 7.4)

0.40592098

Log P

0.69024134

Molar Refractivity

41.0794

Polarizability

14.836741

Polar Surface Area

57.61

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

2-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione

Synonyms

2-Hydroxy-1H-isoindole-1,3(2H)-dione2-hydroxyisoindoline-1,3-dione2-Hydroxy-1H-isoindole-1,3(2H)-dioneN-Hydroxyphthalimide2-Hydroxyisoindolin-1,3-dioneN-羟基邻苯二甲酰亚胺N-Hydroxyphthalimide2-hydroxy-2,3-dihydro-1H-isoindole-1,3-dioneNHPI

IUPAC Traditional name

N-hydroxyphthalimide

Names and Identifiers

Registration numbers

CAS Number

EC Number

MDL Number

Beilstein Number

Merck Index

PubChem SID

1620582532487998524895686

PubChem CID

10665

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02151307

Crystalline
Used as additive in DCC method of peptide synthesis to increase yield of product.

05203357

MP Biomedicals Rare Chemical collection

Sigma Aldrich

H53704

Packaging
100, 500 g in poly bottle
5 g in glass bottle
Application
For preparation of amine nucleosides for coupling into non-anionic, anti-sense oligonucleosides.1

Molecule Details

References

PubChem Literature

From Data Sources

• O-Alkylation followed by hydrazinolysis gives O-alkylhydroxylamines: Bull. Soc. Chim. Fr., 833 (1976). Copper-promoted coupling with arylboronic acids, followed by hydrazinolysis, affords O-arylhydroxylamines: Org. Lett., 3, 139 (2001).

• Efficient electron carrier for electrochemical oxidation of alcohols: J. Chem. Soc., Chem. Commun., 479 (1983). Has also been found to be an efficient catalyst for non-electrochemical oxidation of benzylic groups in benzonitrile solution with atmospheric pressure oxygen: J. Org. Chem., 60, 3934 (1995). The method can be extended to alkanes by the use of a catalyst such as 0.5-1 mol% Co(acac)₂. Thus cyclohexane is oxidized to cyclohexanone and adipic acid; adamantane gives mainly 1-adamantanol with minor amounts of 2-adamantanone and 1,3-adamantanediol: J. Org. Chem., 61, 4520 (1996). Under similar conditions alkynes can be oxygenated to ɑ?-acetylenic ketones in good yields: Chem. Commun., 2037 (1998).

• Additive in the carbodiimide method of peptide coupling, leading to decreased racemization: J. Am. Chem. Soc., 89, 7151 (1967). For alternative reagents, see N,N'-Dicyclohexylcarbodiimide, A10973, and Appendix 6.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

2-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione

Synonyms

IUPAC Traditional name

N-hydroxyphthalimide

Registration numbers

CAS Number

EC Number

MDL Number

Beilstein Number

Merck Index

PubChem SID

1620582532487998524895686

PubChem CID

10665

Molecule Details

MP Biomedicals

02151307

Crystalline
Used as additive in DCC method of peptide synthesis to increase yield of product.

05203357

MP Biomedicals Rare Chemical collection

Sigma Aldrich

H53704

Packaging
100, 500 g in poly bottle
5 g in glass bottle
Application
For preparation of amine nucleosides for coupling into non-anionic, anti-sense oligonucleosides.1

References

PubChem Literature

From Data Sources

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:53490