82082-50-6

Basic information

• Product Name: N-BENZYL 2-BROMOBENZAMIDE
• Synonyms: AURORA 7999;N-BENZYL 2-BROMOBENZAMIDE;N-Benzyl-2-bromobenzamide 98%;N-Benzyl-2-bromobenzamide98%
• CAS NO: 82082-50-6
• Molecular Formula: C₁₄H₁₂BrNO
• Molecular Weight: 290.16
• Product Categories: blocks;Bromides;Carboxes
• Mol File: 82082-50-6.mol

Chemical Properties

• Melting Point: 110-114
• Boiling Point: 438 °C at 760 mmHg
• Flash Point: 218.7 °C
• Appearance: /
• Density: 1.404 g/cm³
• Vapor Pressure: 7.13E-08mmHg at 25°C
• Refractive Index: 1.614
• CAS DataBase Reference: N-BENZYL 2-BROMOBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYL 2-BROMOBENZAMIDE(82082-50-6)
• EPA Substance Registry System: N-BENZYL 2-BROMOBENZAMIDE(82082-50-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 82082-50-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-Benzyl 2-bromobenzamide is used as a building block in the creation of various pharmaceutical and agrochemical products, contributing to the development of new compounds with potential therapeutic and agricultural applications.
Used in Dye Production:
This chemical compound also serves as an intermediate in the production of dyes, playing a crucial role in the synthesis of colorants for various industries.
Safety Precautions:
Due to its potential to cause skin and eye irritation, N-Benzyl 2-bromobenzamide should be handled with care. It is recommended to work in a well-ventilated area and use appropriate protective equipment to minimize health risks during its use in chemical processes.

InChI:InChI=1/C14H12BrNO/c15-13-9-5-4-8-12(13)14(17)16-10-11-6-2-1-3-7-11/h1-9H,10H2,(H,16,17)

Upstream product

• 88-65-3 2-bromobenzoic-acid 
• 79985-00-5 2-bromo-benzoyl bromide 
• 100-46-9 benzylamine 
• 4001-73-4 2-Bromobenzamide 
• 100-52-7 benzaldehyde 
• 134419-77-5 1-(2-bromophenyl)-3-phenylprop-2-yn-1-one 
• 29237-95-4 chloro-benzyl amine 
• 6630-33-7 ortho-bromobenzaldehyde 
• 622-79-7 benzyl azide 
• 100-39-0 benzyl bromide 
• 2042-37-7 o-cyanobromobenzene 
• 100253-83-6 N-benzyl-N-nitrosopivalamide 
• 7154-66-7 2-bromobenzoic acid chloride 

Downstream Products

• 19793-96-5 (Z)-2-benzyl-3-benzylidene-2,3-dihydro-1H-isoindolin-1-one 
• 202004-86-2 (Z)-3-(p-methoxyphenyl)methylidene-N-benzyl isoindolin-1-one 
• 1127896-72-3 (Z)-2-benzyl-3-(4-methylbenzylidene)-2,3-dihydro-isoindol-1-one 
• 60940-33-2 2-benzylbenzo[d][1,2]selenazol-3(2H)-one 
• 293744-55-5 N-benzyl-2-(2'-phenylethynyl)benzamide 
• 87861-97-0 5-(benzyl)phenanthridin-6(5H)-one 
• 1401880-96-3 5-benzyl-2,3-dimethylphenanthridin-6(5H)-one 
• 1401880-97-4 5-benzyl-2,3-dimethoxyphenanthridin-6(5H)-one 
• 1401880-98-5 5-benzyl-2,3-difluorophenanthridin-6(5H)-one 
• 1086599-15-6 (Z)-3-(4-fluorobenzylidene)-2-benzylisoindolin-1-one 
• 1423016-43-6 (Z)-3-(3-methylbenzylidene)-2-benzylisoindolin-1-one 
• 1423016-44-7 (Z)-2-benzyl-3-(cyclohexylmethylene)isoindolin-1-one 
• 2527-62-0 bis[2-(N-benzylcarbamoyl)phenyl] disulfide 
• 19857-37-5 3-benzyl-2-phenyl-3,4-dihydroquinazolin-4-one 

Relevant articles and documents

Rapid construction of C4-substituted phenanthridinones through palladium-catalyzed domino N-arylation/aryl-aryl coupling process

An excellent chemo- and regioselective palladium-catalyzed cascade intermolecular N-arylation/aryl-aryl coupling process has been developed. Employing Pd(TFA)2, PCy3?HBF4, K2CO3 and 1,4-dioxane in an oil bath at 100°C for 12 h, diverse C4-substituted phenanthridinones are synthesized from o-bromobenzamides in 42-92% yield. Broad substrate scope and excellent functional group tolerance are observed. The synthetic utility of this method is illustrated by the further derivatization to prepare multiple-substituted phenanthridinones in 30-75% yield.

Synthesis of pyrimido[2,1-a]isoindolone and isoindolo[2,1-a]quinazolinoneviaintramolecular aza-Prins type reaction

A novel aza-Prins type cyclization reaction involvingN-acyliminium ions and amides is reported for the synthesis of tetrahydropyrimido[2,1-a]isoindole-2,6-dione and 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives in excellent yields. The strategy features inexpensive reagents, mild reaction conditions, and metal-free synthesis of N-heterocyclic frameworks. Further, post-synthetic modification results in the unprecedented formation of its triazole, tetracyclic diazacyclopenta[def]phenanthrene-1,4(9a1H)-dione and carbonyl derivatives.

Structure-Activity Studies Reveal Scope for Optimisation of Ebselen-Type Inhibition of SARS-CoV-2 Main Protease

The reactive organoselenium compound ebselen is being investigated for treatment of coronavirus disease 2019 (COVID-19) and other diseases. We report structure-activity studies on sulfur analogues of ebselen with the Severe Acute Respiratory Syndrome coronavirus 2 (SARS-CoV-2) main protease (Mpro), employing turnover and protein-observed mass spectrometry-based assays. The results reveal scope for optimisation of ebselen/ebselen derivative- mediated inhibition of Mpro, particularly with respect to improved selectivity.

Reductive N-alkylation of primary amides using nickel-nanoparticles

Here we report Ni-nanoparticles as reusable catalysts for reductive N-alkylation of amides. These Ni-nanoparticles based catalysts have been prepared by the template synthesis of tartaric acid and 2-methyl imidazole ligated Ni-complex on SiO2 and subsequent pyrolysis under argon. Applying optimal Ni-nanostructured catalyst, N-alkylation of aromatic and heterocyclic primary amides with different aldehydes in presence of molecular hydrogen was performed to access structurally diverse N-alkylated amides in good to excellent yields. In addition, the applicability of this N-alkylation protocol has been demonstrated for the selective functionalization of primary amide group in Levetiracetam drug.

A solid-supported arylboronic acid catalyst for direct amidation

An efficient heterogeneous amidation catalyst has been prepared by co-polymerisation of styrene, DVB with 4-styreneboronic acid, which shows wide substrate applicability and higher reactivity than the equivalent homogeneous phenylboronic acid, suggesting potential cooperative catalytic effects. The catalyst can be easily recovered and reused; suitable for use in packed bed flow reactors.

Base-promoted amide synthesis from aliphatic amines and ynones as acylation agents through C-C bond cleavage

A new protocol for the synthesis of amides via base-promoted cleavage of the C(sp)-C(CO) bond of ynones with aliphatic primary and secondary amines under transition-metal-, ligand-, and oxidant-free conditions has been developed. This method exhibits a wide substrate scope, high functional group tolerance and exclusive chemoselectivity, as well as mild reaction conditions.

Method for preparing amide compound from 2-diazo-1, 3-dicarbonyl compound as acylating agent

The invention provides a method for preparing an amide compound from a 2-diazo-1, 3-dicarbonyl compound as an acylating agent under non-metallic catalysis and neutral conditions. The method uses 2-diazo-1, 3-dicarbonyl compound as a raw material and carries out different benzoyl protection on different amino compounds so that a series of amide compounds are prepared. The method is carried out under neutral conditions, prevents the limitation of reaction substrates under conventional alkaline conditions, and has mild reaction conditions, high reaction efficiency and a simple operation method. The method provides a new and convenient method for preparation of amide compounds and protection of amino groups and can be used in the fields of chemical medicine, biology and materials.

Ligandless Nickel-Catalyzed Ortho-Selective Directed Trifluoromethylthiolation of Aryl Chlorides and Bromides Using AgSCF3

A mild protocol for Ni-catalyzed trifluoromethylthiolation of aryl chlorides and bromides is described herein. The method utilizes AgSCF3 as an easily accessible nucleophilic trifluoromethylthiolating reagent and does not require any ligands or additives. Ortho-selectivity is achieved using a variety of directing groups such as imines, pyridines, and oxazolines for 24 examples in up to 95% yield.

Practical Synthesis of Phenanthridinones by Palladium-Catalyzed One-Pot C-C and C-N Coupling Reaction: Extending the Substrate Scope to o-Chlorobenzamides

A highly efficient construction of phenanthridinone derivatives from o-halobenzamides was developed by using a phosphine-free palladium catalyst in N,N-dimethylacetamide. The domino reaction proceeds through a sequential C-C and C-N bond-formation process in one pot. This protocol exhibits broad substrate scope and affords a series of phenanthridinones in up to 93 % yield. Importantly, the protocol could also be applied for the less reactive o-chlorobenzamides. The approach constitutes the first example of the synthesis of phenanthridinones from this kind of substrate. Moreover, the success of a gram-scale reaction demonstrated that this operationally simple process is scalable.

AIBN-initiated metal free amidation of aldehydes using N-chloroamines

An efficient and environmentally benign amidation of aldehydes with N-chloroamines has been developed using AIBN as an initiator. This methodology offers a metal free and base free approach and is endowed with mild reaction conditions, high yields, and good functional group tolerance.