40101-31-3

Usage

Uses

Used in Pharmaceutical Industry:
N-(4-Bromophenyl)phthalimide is utilized as a key intermediate in the synthesis of various drugs, playing a crucial role in drug design and the development of new therapeutic agents.
Used in Organic Synthesis:
N-(4-BROMOPHENYL)PHTHALIMIDE serves as an intermediate in organic synthesis, contributing to the creation of complex molecules and compounds.
Used in Palladium-Catalyzed Cross Coupling Reactions:
N-(4-Bromophenyl)phthalimide is employed as a coupling partner in palladium-catalyzed cross coupling reactions, a significant method in modern organic chemistry for forming carbon-carbon bonds, which is vital for the synthesis of a wide array of chemical compounds, including pharmaceuticals and agrochemicals.

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 
• 2493-02-9 4-bromophenyl isocyanate 
• 19336-83-5 N-<4-Bromphenyl>-phtalsaeureamid 
• 2101-88-4 1-azido-4-bromobenzene 
• 6341-55-5 N,N'-bis(p-bromophenyl)urea 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 136918-14-4 phthalimide 
• 108-86-1 bromobenzene 
• 524-38-9 N-hydroxyphthalimide 
• 83-33-0 inden-1-one 
• 201230-82-2 carbon monoxide 
• 313268-47-2 2-iodo N-(4-bromophenyl)benzamide 
• 88-67-5 2-Iodobenzoic acid 

Downstream Products

• 875-51-4 4-Bromo-2-nitroaniline 
• 53324-38-2 4-bromo-3-nitroaniline 
• 36127-32-9 4-prenylaniline 
• 235086-03-0 acetic acid 1-methyl-2-{2-methyl-6-[4-(3-methyl-but-2-enyl)-phenylamino]-3,4-dioxo-cyclohexa-1,5-dienyl}-ethyl ester 
• 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 

Relevant academic research and scientific papers

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.

“On water” nano-Cu2O-catalyzed CO-free one-pot multicomponent cascade cyanation-annulation-aminolysis reaction toward phthalimides

An efficient nano-Cu2O-catalyzed cascade multicomponent reaction of 2-halobenzoic acids and trimethylsilyl cyanide with diverse amines was developed using water as a solvent, affording versatileN-substituted phthalimide derivatives in moderate to excellent yields. This novel strategy features carbon monoxide gas-free, environmentally benign, one-pot multistep transformation, commercially available reagents, a cheap catalyst without any additives, wide functional group tolerance, and operational convenience.

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.

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.

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.

Br?nsted acid mediated intramolecular cyclopropane ring expansion/[4 + 2]-cycloaddition

A cascade reaction of 3-hydroxy-2-phenylisoindolin-1-one and cyclopropyl ketone has been developed via a Br?nsted acid-promoted ring-opening/intramolecular cross-cycloaddition/[4 + 2]-cycloaddition process. The developed methodology provides straightforward access to pentacyclic isoindolin-1-one derivatives under simple reaction conditions.

Novel method for constructing N-(4-bromophenyl)phthalimide for one step from imine as initial raw material

The invention discloses a method for constructing N-(4-bromophenyl)phthalimide for one step from imine as an initial raw material. The method uses (E)-N-(4-bromophenyl)-1-phenyl methylenimine as a reaction raw material for constructing the N-(4-bromopheny

Carbonylation Access to Phthalimides Using Self-Sufficient Directing Group and Nucleophile

Herein we report a novel palladium-catalyzed oxidative carbonylation reaction for the synthesis of phthalimides with high atom- and step-economy. In our strategy, the imine and H2O, which are generated in situ from the condensation of aldehyde and amine, serve as self-sufficient directing group and nucleophile, respectively. This method provides rapid access to phthalimides starting from readily available materials in a one-pot manner. Various phthalimide derivatives are constructed efficiently, including medicinally and biologically active phthalimide-containing compounds.

NITROGEN-CONTAINING BIOPOLYMER-BASED CATALYSTS, THEIR PREPARATION AND USES IN HYDROGENATION PROCESSES, REDUCTIVE DEHALOGENATION AND OXIDATION

The present invention relates to a process for the preparation of a nitrogen containing biopolymer-based catalyst by pyrolysis of a metal complex with a nitrogen-containing biopolymer and to the nitrogen containing biopolymer-based catalysts obtainable by this process. In particular, the invention relates to a nitrogen containing biopolymer-based catalyst comprising metal particles and at least one nitrogen containing carbon layer. The invention also relates to the use of a nitrogen containing biopolymer-based catalyst in a hydrogenation process, preferably in a process for hydrogenation of nitroarenes, nitriles or imines; in a reductive dehalogenation process of C-X bonds, wherein X is CI, Br or I, preferably in a process for dehalogenation of organohalides or in a process for deuterium labelling of arenes via dehalogenation of organohalides; or in an oxidation process. Further, the invention relates to a metal complex with the nitrogen containing biopolymer, wherein the metal is a transition metal selected from the group consisting of manganese, ruthenium, cobalt, rhodium, nickel, palladium and platinum, preferably cobalt or nickel, and wherein the nitrogen containing biopolymer is selected from chitosan, chitin and a polyamino acid, preferably chitosan or chitin.

Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives

The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.