2142-01-0

Basic information

• Product Name: N-BENZYLPHTHALIMIDE
• Synonyms: BENZYLPHTHALIMIDE;N-BENZYLPHTHALIMIDE;SALOR-INT L253022-1EA;N-BENZYLPHTALIMIDE;2-Benzyl-1,3-isoindolinedione;2-Benzylisoindoline-1,3-dione;2-Benzyl-1H-isoindole-1,3(2H)-dione;2-(benzyl)isoindoline-1,3-quinone
• CAS NO: 2142-01-0
• Molecular Formula: C₁₅H₁₁NO₂
• Molecular Weight: 237.25
• EINECS: 218-395-5
• Product Categories: N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;Carbonyl Compounds;Cyclic Imides;Organic Building Blocks
• Mol File: 2142-01-0.mol
• Article Data: 175

Chemical Properties

• Melting Point: 114-116 °C(lit.)
• Boiling Point: 379.79°C (rough estimate)
• Flash Point: 179.779 °C
• Appearance: white crystalline powder
• Density: 1.3430
• Vapor Pressure: 2.19E-06mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -2.12±0.20(Predicted)
• CAS DataBase Reference: N-BENZYLPHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYLPHTHALIMIDE(2142-01-0)
• EPA Substance Registry System: N-BENZYLPHTHALIMIDE(2142-01-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 2142-01-0(Hazardous Substances Data)

Usage

Description

N-Benzylphthalimide (NBPT), also known as 2-benzylisoindoline-1,3-dione, is an N-substituted phthalimide derived from the reaction of phthalic anhydride with benzyl amine in glacial acetic acid. It is a white crystalline powder with a roof-shaped molecular structure, featuring a planar cyclic imide and a phenyl ring connected by a methylene group. The crystal structure of N-Benzylphthalimide consists of parallel layers of phthalimides that stack along the a axis.

Uses

Used in Chemical Syntheses:
N-Benzylphthalimide is used as a key intermediate in the synthesis of various organic compounds, including 2-benzyl-1,1,3,3-tetraphenylisoindoline and tailor-made highly fluorous porphyrin derivatives. It serves as a crucial building block for the development of complex molecular structures with potential applications in various fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-Benzylphthalimide is utilized as a starting material for the synthesis of various pharmaceutical compounds, such as N-benzylisoindole. These synthesized compounds can be further used in the development of drugs with specific therapeutic properties.
Used in Research and Development:
N-Benzylphthalimide is also employed in research and development for the study of its chemical properties, reactivity, and potential applications in the synthesis of novel compounds. The vibrational spectra of NBPT have been recorded and assigned, providing valuable information for researchers working with this compound.

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, 1943The Journal of Organic Chemistry, 47, p. 2785, 1982 DOI: 10.1021/jo00135a021Tetrahedron Letters, 11, p. 2691, 1970

InChI:InChI=1/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

Upstream product

• 110-86-1 pyridine 
• 91-22-5 quinoline 
• 19357-07-4 2-(benzylcarbamoyl)benzoic acid 
• 85-44-9 phthalic anhydride 
• 538-32-9 benzylurea 
• 2835-06-5 phenylglycin 
• 100-46-9 benzylamine 
• 136918-14-4 phthalimide 
• 100-44-7 benzyl chloride 
• 17564-64-6 N-(chloromethyl)phthalimide 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 71-43-2 benzene 
• 118-29-6 2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione 
• 1074-82-4 potassium phtalimide 

Downstream Products

• 136918-14-4 phthalimide 
• 100965-07-9 N-(α-bromo-benzyl)-phthalimide 
• 100-52-7 benzaldehyde 
• 13380-32-0 2-benzylisoindolin-1-one 
• 14160-15-7 N-benzylthiophthalimide 
• 17448-14-5 2-benzyl-3-hydroxy-2,3-dihydro-isoindol-1-one 
• 19357-07-4 2-(benzylcarbamoyl)benzoic acid 
• 35970-03-7 2-(2-nitrobenzyl)isoindoline-1,3-dione 
• 62133-07-7 2-(4-nitrobenzyl)-1H-isoindole-1,3(2H)-dione 
• 402925-20-6 4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzenesulphonyl chloride 
• 100-46-9 benzylamine 
• 135382-78-4 ZIN⁽⁰¹⁶⁾C₀₀₆₅₁ 
• 82894-83-5 2-benzyl-1,1,3,3-tetramethylisoindoline 
• 86166-00-9 2-benzyl-1-ethyl-1,3,3-trimethylisoindoline 

Relevant articles and documents

Comparative study of chemically immobilized and conventional homogeneous ionic liquids as phase-transfer catalysts for the N -alkylation of heterocyclic compounds

Various ionic liquids (ILs) were screened for their phase-transfer catalytic (PTC) activity using the N-alkylation of nitrogen heterocycles as the model reaction. Immobilized ILs behaved extremely well and proved to be far better catalysts than conventional homogeneous PTCs in terms of their stability, easy recovery, and reusability. The investigation also demonstrated that quaternary tetraalkylammonium salts offer very high catalytic activity, whereas aromatic heterocyclic tetravalent nitrogen catalysts (imidazolium- and pyridinium-based salts) were poorly active.

Efficient one-pot synthesis of N-substituted phthalimides/naphthalimides from azides and anhydrides by iodotrimethylsilane

N-Substituted phthalimides and naphthalimides have been obtained in good to excellent yields, employing chlorotrimethylsilane and sodium iodide (in situ generation of iodotrimethylsilane) from corresponding azides and anhydrides under mild conditions.

A Facile One-pot Synthesis of N-Substituted Phthalimides Using a Catalytic Amount of Crown Ether

N-Substituted phthalimides, intermediates of the Gabriel synthesis, were obtained in high yields (84-100percent) by the addition of a catalytic amount of 18-crown-6 to the reaction of potassium phthalimide and alkyl halides in toluene.

Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides

Ninhydrin bis-acetals give access to 8-ring lactones, benzocyclo-butenes and spirocyclic orthoanhydrides through photoextrusion and tandem photoextrusion reactions. Syntheses of fimbricalyxlactone B, isoshihunine and numerous biologically-relevant heteroc

Solvent-free, Efficient Transamidation of Carboxamides with Amines Catalyzed by Recyclable Sulfated Polyborate Catalyst

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Tunable System for Electrochemical Reduction of Ketones and Phthalimides

Herein, we report an efficient, tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants. By utilizing NaN3 as the electrolyte and graphite felt as both the cathode and the anode, we were able to selectively reduce the carbonyl groups of the substrates to alcohols, pinacols, or methylene groups by judiciously choosing the solvent and an acidic additive. The reaction conditions were compatible with a diverse array of functional groups, and phthalimides could undergo one-pot reductive cyclization to afford products with indolizidine scaffolds. Mechanistic studies showed that the reactions involved electron, proton, and hydrogen atom transfers. Importantly, an N3/HN3 cycle operated as a hydrogen atom shuttle, which was critical for reduction of the carbonyl groups to methylene groups.