N-Hydroxyphthalimide (BAT-004872)
* For research use only

Additive in to DCC method of peptide synthesis used to improve yield of optically pure product.

Catalog number
CAS number
Molecular Formula
Molecular Weight
2-Hydroxy-1H-isoindole-1,3(2H)-dione Phthaloxime
Off-white to yellow crystalline powder
≥ 99% (Assay)
1.64 g/cm3
Melting Point
231-237 ºC
Boiling Point
290.19°C (rough estimate)
Store at RT
1.Mutagenicity of new lead compounds to treat sickle cell disease symptoms in a Salmonella/microsome assay.
dos Santos JL1, Varanda EA, Lima LM, Chin CM. Int J Mol Sci. 2010 Feb 25;11(2):779-88. doi: 10.3390/ijms11020779.
A series of phthalimide derivatives planned as drugs candidates to treat the symptoms of sickle cell anemia were evaluated in a mutagenicity test using strains of Salmonella typhimurium TA100 and TA102, without and with addition of S9 mixture, with the aim to identify the best structural requirements for a drug candidate without genotoxic activity. The compounds (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl nitrate (1); (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl nitrate (2); 3-(1,3-dioxo-1,3-dihydro-2H-iso-indol-2-yl)benzyl nitrate (3); 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-hydroxy-benzenesulfonamide (4); 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)benzyl nitrate (5) and 2-[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]ethyl nitrate (6) presented mutagenic potency ranging between 0-4,803 revertants/micromol. These results allowed us to propose that a methyl spacer linked to a nitrate ester subunit associated to meta aromatic substitution decreases mutagenicity.
2.Influence of the medium's viscosity on the kinetics of hydrogen atom self-exchange for N-hydroxy phthalimide/piperidine-N-oxyl (NHPI/PINO˙) measured by CW-ESR spectroscopy.
Bächle J1, Goni F, Grampp G. Phys Chem Chem Phys. 2015 Oct 28;17(40):27204-9. doi: 10.1039/c5cp04921k.
CW-ESR line broadening experiments are used to investigate the kinetics of fast hydrogen atom self-exchange reactions. The system NHPI/PINO˙ was studied in five different aprotic organic solvents at room temperature with a focus on the influence of the viscosity of the medium. Our findings support the theoretical descriptions derived from the statistical dynamics of the impact of the reorganization of the medium. In an Arrhenius type description the influence appears in the preexponential factor as a linear dependence on the dynamic viscosity.
3.Pharmacokinetics, metabolism and excretion of [(14)C]-lenalidomide following oral administration in healthy male subjects.
Chen N1, Wen L, Lau H, Surapaneni S, Kumar G. Cancer Chemother Pharmacol. 2012 Mar;69(3):789-97. doi: 10.1007/s00280-011-1760-3. Epub 2011 Oct 29.
PURPOSE: Assessment of the absorption, metabolism and excretion of [(14)C]-lenalidomide in healthy male subjects following a single oral dose.
4.Copper-catalyzed aerobic C - C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones.
Tnay YL1, Chiba S. Chem Asian J. 2015 Apr;10(4):873-7. doi: 10.1002/asia.201403196. Epub 2014 Nov 13.
The transformation of cyclic hemiacetals (lactols) into lactones has been achieved by Cu-catalyzed aerobic CC bond cleavage in the presence of N-hydroxy phthalimide (NHPI). The present process is composed of a multistep sequence including a) formation of exo-cyclic enol ethers by dehydration; b) addition of phthalimide N-oxyl radical to the enol ethers followed by trapping of the resulting C-radicals with molecular oxygen to form peroxy radicals; c) reductive generation of oxy radicals and subsequent β-radical fragmentation to generate lactones.
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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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