14835-59-7

Basic information

• Product Name: N-(2-Biphenylyl)phthalic acid imide
• Synonyms: N-(2-Biphenylyl)phthalic acid imide;N-(2-Biphenylyl)phthalimide
• CAS NO: 14835-59-7
• Molecular Formula: C₂₀H₁₃NO₂
• Molecular Weight: 299.32
• Mol File: 14835-59-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 165-166 °C
• Boiling Point: 498.6°Cat760mmHg
• Flash Point: 232.5°C
• Appearance: /
• Density: 1.289g/cm³
• Vapor Pressure: 4.47E-10mmHg at 25°C
• Refractive Index: 1.669
• PKA: -0.58±0.20(Predicted)
• CAS DataBase Reference: N-(2-Biphenylyl)phthalic acid imide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-Biphenylyl)phthalic acid imide(14835-59-7)
• EPA Substance Registry System: N-(2-Biphenylyl)phthalic acid imide(14835-59-7)

Safety Data

• Hazardous Substances Data: 14835-59-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H13NO2/c22-19-16-11-4-5-12-17(16)20(23)21(19)18-13-7-6-10-15(18)14-8-2-1-3-9-14/h1-13H

Upstream product

• 520-03-6 N-phenylphthalimide 
• 65-85-0 benzoic acid 
• 85-44-9 phthalic anhydride 
• 90-41-5 2-phenylaniline 

Downstream Products

• 63558-92-9 isoindolo<2,1-f>phenanthridin-10(14bH)-one 
• 128425-80-9 14b-benzyl-isoindolo<2,1-f>phenanthridin-10(14bH)-one 
• 63558-98-5 2-phenanthridin-6-yl-benzoic acid methyl ester 
• 57877-20-0 2-biphenyl-2-yl-3-hydroxy-2,3-dihydro-isoindol-1-one 
• 128425-75-2 3-benzyl-2-biphenyl-2-yl-2,3-dihydro-3-hydroxyisoindol-1-one 
• 54893-50-4 2-phenanthridin-6-yl-benzoic acid 

Relevant articles and documents

Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides

We report on cyclic imides as weak directing groups for selective monohydroxylation reactions using ruthenium catalysis. Whereas acyclic amides are known to promote the hydroxylation of the C(sp2)-H bond enabling five-membered ring ruthenacycle intermediates, the cyclic imides studied herein enabled the hydroxylation of the C(sp2)-H bond via larger six-membered ruthenacycle intermediates. Furthermore, monohydroxylated products were exclusively obtained (even in the presence of overstoichiometric amounts of reagents), which was rationalized by the difficulty to accommodate coplanar intermediates once the first hydroxyl group was introduced into the substrate. The same reactivity was observed in the presence of palladium catalysts.

Design, synthesis and protection against pentylenetetrazole-induced seizure of N-aryl derivatives of the phthalimide pharmacophore

A series of compounds including N-aryl substituents of phthalimide and 4-nitrophthalimide were synthesized and evaluated for their anticonvulsant properties. The in vivo screening data suggest that all the analogs have the ability to protect against pentylenetetrazole-induced seizures. These compounds exerted their maximal effects 30 min after administration. The most potent compound in both, tonic and clonic seizure was 1-naphthyl derivative (comp. 6), which was more active than the reference drug known as Phenytoin. Using an open pore model of the Na channel, these anticonvulsants were docked in the active site and examined in relation to the residues identified by mutagenesis as important for their binding energies. Docking studies revealed that all compounds (1-13) interacted mainly with residues II-S6 of NaV1.2 by making hydrogen bonds and additional hydrophobic interactions with domain I and II in the channel's inner pore.

Novel biological response modifiers: Phthalimides with tumor necrosis factor-α production-regulating activity

Novel N-substituted phthalimides (2-substituted 1H-isoindole-1,3- diones) were prepared, and their effects on tumor necrosis factor-α (TNF- α) production by human leukemia cell line HL-60 stimulated with 12-O- tetradecanoylphorbol 13-acetate (TPA) or okadaic acid (OA) were examined. A structure-activity relationship study of the N-phenylphthalimides and N- benzylphthalimides revealed that their enhancing effect on TPA-induced TNF- α production by HL-60 cells and their inhibiting effect on OA-induced TNF- α production by HL-60 cells are only partially correlated.