N-BENZYLPHTHALIMIDE Chemical Properties

Melting point:

114-116 °C(lit.)

Boiling point:

379.79°C (rough estimate)

Density 

1.3430

refractive index 

1.5500 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

-2.12±0.20(Predicted)

color 

White to Light yellow

CAS DataBase Reference

2142-01-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-22

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29251900

MSDS

• Language:English Provider:SigmaAldrich

N-BENZYLPHTHALIMIDE Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

N-Benzylphthalimide may be used in the following syntheses:

• 2-benzyl-1,1,3,3-tetraphenylisoindoline
• tailor-made highly fluorous porphyrin derivatives
• N-benzylisoindole

Definition

ChEBI: N-Benzylphthalimide is a member of isoindoles.

Preparation

In a flask equipped with a reflux condenser, a mixture of 300 gm (2.04 mole) of phthalimide, 140 gm (1.09 mole) of potassium carbonate, and 300 gm (2.37 mole) of benzyl chloride is refluxed for 3 hr. The excess benzyl chloride is removed by steam distillation and the benzyl phthalimide which crystallizes out is filtered by suction. The product is washed with water, with 400 ml of 60% ethanol, and then dried to afford 360-375 gm (74-77%), m.p. 116°C (recrystallized from acetic acid).

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 2, p. 83, 1943
The Journal of Organic Chemistry, 47, p. 2785, 1982 DOI: 10.1021/jo00135a021
Tetrahedron Letters, 11, p. 2691, 1970

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.

N-BENZYLPHTHALIMIDE(2142-01-0)Related Product Information

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