5467-04-9

Basic information

• Product Name: N,N'-(p-Phenylene)bisbenzamide
• Synonyms: N,N'-(1,4-Phenylene)bisbenzamide;N,N'-(p-Phenylene)bisbenzamide;N-(4-(Benzoylamino)Phenyl)Benzamide;N,N'-(1,4-Phenylene)dibenzamide
• CAS NO: 5467-04-9
• Molecular Formula: C₂₀H₁₆N₂O₂
• Molecular Weight: 316.35
• Mol File: 5467-04-9.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N,N'-(p-Phenylene)bisbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-(p-Phenylene)bisbenzamide(5467-04-9)
• EPA Substance Registry System: N,N'-(p-Phenylene)bisbenzamide(5467-04-9)

Safety Data

• Hazardous Substances Data: 5467-04-9(Hazardous Substances Data)

Usage

General Description

The chemical N,N'-(p-phenylene)bisbenzamide, also known as PPD, is a synthetic compound consisting of two benzamide groups linked by a p-phenylene bridge. It is commonly used as a coupling reagent in the synthesis of peptides and as an inhibitor of protein kinase C. PPD is a white crystalline powder that is sparingly soluble in water and organic solvents. It is considered to be relatively stable under normal handling and storage conditions. PPD is primarily used in the research and pharmaceutical industries for its ability to facilitate peptide bond formation and its potential therapeutic properties as a protein kinase C inhibitor.

Upstream product

• 98-88-4 benzoyl chloride 
• 106-50-3 1,4-phenylenediamine 
• 16720-35-7 N,N'-2,5-cyclohexadiene-1,4-diylidenebis 
• 65-85-0 benzoic acid 
• 110-89-4 piperidine 
• 93-97-0 benzoic acid anhydride 
• 10364-94-0 1-benzoylimidazole 
• 624-18-0 benzene-1,4-diamine hydrochloride 
• 100-51-6 benzyl alcohol 
• 64-19-7 acetic acid 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 17625-83-1 N-(4-aminophenyl)benzamide 

Downstream Products

• 15999-99-2 N,N'-p-phenylene-bis-benzimidoyl chloride 
• 24118-33-0 2,5-bis-benzoylamino-[1,4]benzoquinone 
• 308291-66-9 N,N'-dibenzoyl-2,6-dichloro-1,4-benzoquinone diimine 
• 314751-39-8 N,N'-(2,6-dichloro-p-phenylene)-bis-benzamide 
• 102160-68-9 N,N'-(2,5-dichloro-p-phenylene)-bis-benzamide 
• 66012-79-1 5,5'-diphenyl-1H,1'H-1,1'-p-phenylene-bis-tetrazole 
• 16000-05-8 N,N'-(p-Phenylen)-bis-benzimidsaeure-bis-(4-benzolazo-2-methoxycarbonyl-phenylester) 
• 1237477-97-2 C₂₈H₃₄N₂O₆P₂ 
• 1237477-99-4 C₃₂H₄₅N₂O₉P₃ 
• 1237478-02-2 C₃₆H₅₆N₂O₁₂P₄ 
• 1237477-96-1 N,N'-bis[(diphenylphosphoryl)phenylmethylidene]-1,4-benzenediamine 
• 1237477-92-7 (Z,Z)-N,N'-(p-phenylene)dibenzimidoyl dichloride 
• 43036-58-4 2,6-diphenylbenzo[1,2-d:4,5-d']bis(oxazole) 

Relevant articles and documents

Insight into Fundamental Rules of Phenylenediamines Selective Monoacylation by the Comparisons of Kinetic Characteristics in Microreactor

In this paper, the kinetics of acylation reaction of o-phenylenediamine/p-phenylenediamine and benzoic anhydride were determined in microreactors, respectively. A kinetic model was established, all kinetic parameters including reaction orders, reaction rate constants, pre-exponential factors, and activation energies were acquired. Validation experiments showed experimental data fit well with calculated data at different reactant concentrations and residence times. The comparisons of the reaction rate constants and activation energies were summarized to show the difference of chemical reactivities of phenylenediamines. According to the calculation of the kinetic model, the optimized reaction conditions were listed to meet the monoacylation selectivity equal to 97.0%.

One-step synthesis of dicarboxamides through Pd-catalysed aminocarbonylation with diamines as N-nucleophiles

An efficient one-step synthetic strategy was used to prepare a set of dicarboxamides through palladium-catalysed aminocarbonylation of iodoalkenyl and iodoaryl compounds, with use of various alkyl- and aryldiamines as N-nucleophiles. The isolated yields of the dicarboxamides depended significantly on the iodo substrate and diamine structures, as well as on the reaction conditions, the best one (ca. 70%) being achieved with 1-iodocyclohexene as substrate and 1,4-diaminobutane as nucleophile, at 100°C and 30 bar of CO. When iodobenzene was used as model aryl halide, the highest yield of the target dibenzamides (ca. 65%) was obtained with 1,4-diaminobenzene as coupling amine, at 100°C and 10 bar of CO. Preliminary studies on their in vitro cytotoxicity against human lung carcinoma A549 cells showed N,N′(butane-1,4-diyl)dibenzamide and androst-16-ene-based dicarboxamides to be the most efficient cytotoxic agents, with IC50 values of approximately 40 μM.

Probing the intermolecular interactions of aromatic amides containing N-heterocycles and triptycene

A series of aromatic amides incorporated with N-heterocycles or triptycene units are synthesized and studied for probing the effects of such chemical modifications on the intermolecular interactions. Single crystals of a number of heterocyclic amides and the triptycene-containing amide were obtained. Crystal structures, hydrogen bonds, lattice energy, solubility, and melting points were compared amongst relevant molecules. Suitably positioned nitrogen atoms from heterocycles are found to form intramolecular H-bonds with amide NHs at the expense of weakening or disrupting the intermolecular H-bonds. The effects of such H-bonding changes on solubility and melting point are nonetheless limited. Uniquely, the triptycene unit effectively improves the solubility of the amide without tempering the thermal resistance of the molecule. This journal is the Partner Organisations 2014.