N-BENZYLPHTHALIMIDE
- CAS NO.:2142-01-0
- Empirical Formula: C15H11NO2
- Molecular Weight: 237.25
- MDL number: MFCD00023077
- EINECS: 218-395-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-05-04 17:34:35
What is N-BENZYLPHTHALIMIDE?
Chemical properties
white crystalline powder
The Uses of N-BENZYLPHTHALIMIDE
N-Benzylphthalimide may be used in the following syntheses:
- 2-benzyl-1,1,3,3-tetraphenylisoindoline
- tailor-made highly fluorous porphyrin derivatives
- N-benzylisoindole
What are the applications of Application
N-Benzylphthalimide is an N-substituted phthalimide
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).
Definition
ChEBI: N-Benzylphthalimide is a member of isoindoles.
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.
Properties of N-BENZYLPHTHALIMIDE
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 |
pka | -2.12±0.20(Predicted) |
form | powder to crystal |
color | White to Light yellow |
CAS DataBase Reference | 2142-01-0(CAS DataBase Reference) |
Safety information for N-BENZYLPHTHALIMIDE
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral |
Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for N-BENZYLPHTHALIMIDE
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