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Sigma-Aldrich

N-Benzylphthalimide

99%

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About This Item

Empirical Formula (Hill Notation):
C15H11NO2
CAS Number:
2142-01-0
Molecular Weight:
237.25
EC Number:
218-395-5
MDL number:
MFCD00023077
UNSPSC Code:
12352100
PubChem Substance ID:
24865268
NACRES:
NA.22

Assay

99%

mp

114-116 °C (lit.)

SMILES string

O=C1N(Cc2ccccc2)C(=O)c3ccccc13

InChI

1S/C15H11NO2/c17-14-12-8-4-5-9-13(12)15(18)16(14)10-11-6-2-1-3-7-11/h1-9H,10H2

InChI key

WITXFYCLPDFRNM-UHFFFAOYSA-N

General description

N-Benzylphthalimide (NBPT), also known as 2-benzylisoindoline-1,3-dione, is an N-substituted phthalimide. It has been prepared by reacting phthalic anhydride with benzyl amine in glacial acetic acid. Vibrational spectra of NBPT has been recorded and assigned. NBPT is a roof-shaped molecule with a planar cyclic imide and a phenyl ring connected by a methylene group. Crystal structure of N-benzylphthalimide has parallel layers of phthalimides stack along the a axis.

Application

N-Benzylphthalimide may be used in the following syntheses:
  • 2-benzyl-1,1,3,3-tetraphenylisoindoline
  • tailor-made highly fluorous porphyrin derivatives
  • N-benzylisoindole

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The direct conversion of phthalimides to isoindoles.
Garmaise DL and Ryan A.
Journal of Heterocyclic Chemistry, 7(2), 413-413 (1970)
Impact of molecular size on electron spin relaxation rates of nitroxyl radicals in glassy solvents between 100 and 300 K.
Sato HIDEO, et al.
Molecular Physics, 105(15-16), 2137-2151 (2007)
Vibrational assignment of N-benzylphthalimide and 15N-benzylphthalimide.
Kolev T and Juchnovski I.
Journal of Molecular Structure, 349, 377-380 (1995)
N-benzylphthalimide.
Warzecha K-D, et al.
Acta Crystallographica Section E, Structure Reports Online, 62(6), 2367-2368 (2006)
Highly fluorous porphyrins as model compounds for molecule interferometry.
Tuxen J, et al.
European Journal of Organic Chemistry, 25, 4823-4833 (2011)
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