158525-82-7

Basic information

• Product Name: N-(4-bromophenyl)-4-methylbenzamide
• Synonyms: N-(4-bromophenyl)-4-methylbenzamide;4'-BROMO-4-METHYLBENZANILIDE
• CAS NO: 158525-82-7
• Molecular Formula: C₁₄H₁₂BrNO
• Molecular Weight: 290.15518
• Mol File: 158525-82-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 321.1±35.0 °C(Predicted)
• Appearance: /
• Density: 1.445±0.06 g/cm3(Predicted)
• PKA: 12.89±0.70(Predicted)
• CAS DataBase Reference: N-(4-bromophenyl)-4-methylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-bromophenyl)-4-methylbenzamide(158525-82-7)
• EPA Substance Registry System: N-(4-bromophenyl)-4-methylbenzamide(158525-82-7)

Safety Data

• Hazardous Substances Data: 158525-82-7(Hazardous Substances Data)

Upstream product

• 50882-29-6 (4-bromophenyl)carbamic acid phenyl ester 
• 5084-80-0 tri(4-tolyl)boroxine 
• 2101-88-4 1-azido-4-bromobenzene 
• 874-60-2 4-methyl-benzoyl chloride 
• 99-94-5 p-Toluic acid 
• 106-40-1 4-bromo-aniline 
• 589-87-7 1,4-bromoiodobenzene 
• 619-55-6 para-methylbenzamide 
• 33554-73-3 1-bromo-4-isocyanobenzene 
• 104-87-0 4-methyl-benzaldehyde 
• 104-84-7 para-methylbenzylamine 
• 25569-87-3 benzoic-p-methylbenzoic anhydride 

Downstream Products

• 1453167-79-7 methyl 2-[N-(4-bromophenyl)-4-methylbenzamido]benzoate 
• 1413429-43-2 N-(4-bromophenyl)-4-methyl-N-phenylbenzamide 
• 1075248-98-4 1-(4-bromo-phenyl)-9-phenyl-8-thioxo-2-p-tolyl-1,7,8,9-tetrahydro-purin-6-one 
• 127351-06-8 N-(4-bromophenyl)-4-methylbenzothioamide 

Relevant articles and documents

Traceless selenocarboxylates for the one-pot synthesis of amides and derivatives

We have recently reported a one-pot procedure for glycosyl amides synthesis using selenocarboxylate as traceless reagent. Herein, we present a further application of selenocarboxylate-azide reaction for amide bond formation on a broader range of substrates, including heterocyclic systems and fatty acid. This method proved to be highly efficient for the synthesis of primary and secondary amides, sulfonamides, imides, phosphoramide and also carbamate.

Immobilized Carbodiimide Assisted Flow Combinatorial Protocol to Facilitate Amide Coupling and Lactamization

Through a screen of over one hundred and 30 permutations of reaction temperatures, solvents, carbodiimide resins, and carbodiimide molar equivalences, in the presence, absence, or combination of diisopropylamine and benzotriazole additives, a convenient and first reported carbodiimide polymer-assisted flow approach to effect amide coupling and lactamization was developed. The protocol entails injecting a single solution (1:9 dimethylformamide: dichloromethane) containing a carboxylic acid and an amine or linear peptide sequence into a continuous stream of dichloromethane. The protocol remained viable in the absence of base, did not require carboxylate preactivation which, and in concert with minimal workup requirements, enabled the isolation of products in high yields. Compared to the utilization of untethered carbodiimide reagents, the flow procedure was also observed to provide a degree of racemization safety.

Au(i)/Au(iii)-Catalyzed C-N coupling

Cycling between Au(i) and Au(iii) is challenging, so gold-catalyzed cross-couplings are rare. The (MeDalphos)AuCl complex, which we showed was prone to undergo oxidative addition, is reported here to efficiently catalyze the C-N coupling of aryl iodides and amines. The transformation does not require an external oxidant or a directing group. It is robust and works with a wide scope of aryl iodides and N-nucleophiles under mild conditions. Mechanistic studies, including the NMR and MS characterization of a key aryl amido Au(iii) complex, strongly support a 2e redox cycle in which oxidative addition precedes transmetalation and reductive elimination is the rate-determining step.