40101-31-3

Basic information

• Product Name: N-(4-BROMOPHENYL)PHTHALIMIDE
• Synonyms: N-(P-BROMOPHENYL)PHTHALIMIDE;N-(4-BROMOPHENYL)PHTHALIMIDE;n-(p-bromophenyl)-phthalimid;2-(4-Bromophenyl)-1,3-dihydro-2H-isoindole-1,3-dione;2-(4-Bromophenyl)-2H-isoindole-1,3-dione;2-(4-BROMO-PHENYL)-ISOINDOLE-1,3-DIONE;N-(4-Bromophenyl)phthalimide
• CAS NO: 40101-31-3
• Molecular Formula: C₁₄H₈BrNO₂
• Molecular Weight: 302.12
• Product Categories: N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides
• Mol File: 40101-31-3.mol
• Article Data: 39

Chemical Properties

• Melting Point: 206 °C
• Boiling Point: 449.5°Cat760mmHg
• Flash Point: 225.6°C
• Appearance: /
• Density: 1.5999 (rough estimate)
• Vapor Pressure: 2.85E-08mmHg at 25°C
• Refractive Index: 1.6320 (estimate)
• PKA: -1.41±0.20(Predicted)
• CAS DataBase Reference: N-(4-BROMOPHENYL)PHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-BROMOPHENYL)PHTHALIMIDE(40101-31-3)
• EPA Substance Registry System: N-(4-BROMOPHENYL)PHTHALIMIDE(40101-31-3)

Safety Data

• RTECS: TI4025000
• Hazardous Substances Data: 40101-31-3(Hazardous Substances Data)

Usage

General Description

N-(4-Bromophenyl)phthalimide is a synthetic organic compound that consists of a phthalimide group combined with a 4-bromophenyl moiety. The bromine atom in the compound contributes to its reactivity, making it useful in various synthetic processes. It is primarily used in the pharmaceutical industry for the synthesis of various drugs, as a coupling partner for palladium-catalyzed cross coupling reactions, and as an intermediate in organic synthesis. Overall, it plays a critically important role in drug design and the development of new therapeutic agents. Its molecular formula is C14H8BrNO2 and it may appear as an off-white to beige crystalline powder with a slight odor.

InChI:InChI=1/C14H8BrNO2/c15-9-5-7-10(8-6-9)16-13(17)11-3-1-2-4-12(11)14(16)18/h1-8H

Upstream product

• 85-44-9 phthalic anhydride 
• 106-40-1 4-bromo-aniline 
• 184474-85-9 2-((4-Bromophenyl)amino)isoindoline-1,3-dione 
• 2493-02-9 4-bromophenyl isocyanate 
• 201230-82-2 carbon monoxide 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 2101-88-4 1-azido-4-bromobenzene 
• 136918-14-4 phthalimide 
• 108-86-1 bromobenzene 
• 4376-18-5 Monomethyl phthalate 
• 524-38-9 N-hydroxyphthalimide 
• 83-33-0 inden-1-one 
• 119072-55-8 tert-butylisonitrile 
• 2042-37-7 o-cyanobromobenzene 

Downstream Products

• 875-51-4 4-Bromo-2-nitroaniline 
• 53324-38-2 4-bromo-3-nitroaniline 
• 1280227-55-5 Ir(5,10,15,20-tetra-p-tolylporphyrinate)(C₆H₄(C₈H₄NO₂)) 
• 2142-03-2 2-p-tolylisoindoline-1,3-dione 
• 116053-09-9 N-(4-Bromo-phenyl)-2-hydroxymethyl-benzamide 
• 93-98-1 N-phenyl benzoyl amide 
• 7702-38-7 N-(4-bromophenyl)benzamide 
• 73819-75-7 2-(4-ethynylphenyl)isoindoline-1,3-dione 

Relevant articles and documents

An Oxidation Study of Phthalimide-Derived Hydroxylactams

A systematic study of the oxidation of 3-hydroxy-2-substituted isoindolin-1-ones (hy-droxylactams) and their conversion to the corresponding phthalimides was undertaken using three oxidants. Of special interest was the introduction of nickel peroxide (NiO2 ) as an oxidation system for hydroxylactams and comparison of its performance with the commonly used pyridinium chlorochromate (PCC) and iodoxybenzoic acid (IBX) reagents. Using a range of hydroxylactams, optimal conversions of these substrates to the corresponding imides was achieved with 50 equivalents of freshly prepared NiO2 in refluxing toluene over 5–32 h reaction times. By comparison, oxidations of the same substrates using PCC/silica gel (three equivalents) and IBX (three equivalents) required oxidation times of 1–3 h for full conversion but required lengthier purification. While nominal amounts (~25 mg) of substrate hydroxylactams were used to ascertain conversion, scale-up procedures using all three methods gave good to excellent isolated yields of imides.

Visible-Light-Induced Metal-/Photocatalyst-Free C-H Bond Imidation of Arenes

In this study, a visible-light-induced intermolecular C-H bond imidation of arenes was achieved at ambient condition. By using simple phthalimide with (diacetoxyiodo)benzene and molecular iodine, direct metal-/photocatalyst-free C-N bond formation was achieved. The imidation protocol was designed by using time-dependent density functional theory calculations and experimentally demonstrated for 28 substrates with as high as 96% yield. Mechanistic studies indicated that radical-mediated aromatic substitution occurred via photolysis of N-iodophthalimide under visible-light irradiation.

Palladium Catalyzed Regioselective Synthesis of Substituted Biaryl Amides through Decarbonylative Arylation of Phthalimides

The Pd(OAc)2 catalyzed cross-coupling of N-substituted phthalimides with aryl halide provides a single step direct access of a wide range of synthetically appealing ortho-substituted biarylamides in high yields through unique carbonyl (CO) replacement. The reaction proceeds through a ligand-free condition and is well tolerant to the diverse functionality of both imide and halide units. The reaction negates any requirement of organometallic reagent and needs a shorter reaction time and comparatively lower temperature as required for previously reported decarbonylative processes.