2-Bromo-N-(p-tolyl)benzamide

Base Information

• Chemical Name: 2-Bromo-N-(p-tolyl)benzamide
• CAS No.: 136926-09-5
• Molecular Formula: C₁₄H₁₂BrNO
• Molecular Weight: 290.159
• DSSTox Substance ID: DTXSID001292155
• Mol file: 136926-09-5.mol

Synonyms:136926-09-5;2-Bromo-N-(p-tolyl)benzamide;2-Bromo-N-p-tolyl-benzamide;2-bromo-N-(4-methylphenyl)benzamide;CBMicro_029230;Cambridge id 5116668;SCHEMBL8060238;DTXSID001292155;2-bromo-n -(4-methylphenyl)benzamide;AKOS000190553;BIM-0029355.P001;SR-01000196082;SR-01000196082-1;Z28134690

Chemical Property of 2-Bromo-N-(p-tolyl)benzamide

Chemical Property:

• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 289.01023
• Heavy Atom Count: 17
• Complexity: 261

Purity/Quality:

2-Bromo-N-(p-tolyl)benzamide 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)NC(=O)C2=CC=CC=C2Br

Technology Process of 2-Bromo-N-(p-tolyl)benzamide

There total 3 articles about 2-Bromo-N-(p-tolyl)benzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

4-tolyl iodide (624-31-7) + 2-Bromobenzamide (4001-73-4) → 2-bromo-N-(4-methylphenyl)benzamide (136926-09-5)

Guidance literature:

With silver hexafluoroantimonate; chloro[di(1-adamantyl)-2-dimethylaminophenylphosphine]gold(I); In methanol; at 0 - 80 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.9b03082

Reference yield: 74.0%

p-toluidine (106-49-0,12221-03-3) + 2-bromobenzoic acid chloride (7154-66-7) → 2-bromo-N-(4-methylphenyl)benzamide (136926-09-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1016/j.bmc.2014.03.007

Reference yield: 63.0%

p-toluidine (106-49-0,12221-03-3) + 2-bromobenzoic-acid (88-65-3) → 2-bromo-N-(4-methylphenyl)benzamide (136926-09-5)

Guidance literature:

2-bromobenzoic-acid; With triethylamine; isobutyl chloroformate; In dichloromethane; for 0.25h; Inert atmosphere; Schlenk technique;

p-toluidine; In dichloromethane; at 0 ℃;

DOI:10.1002/ejoc.201501170

upstream raw materials:

p-toluidine

2-bromobenzoic acid chloride

2-bromobenzoic-acid

4-tolyl iodide

Downstream raw materials:

2-Brom-N,4'-dimethylbenzanilid

C₂₈H₂₁NO

3,4-diphenyl-2-(p-tolyl)isoquinolin-1(2H)-one

N²,N^2'-di-p-tolyl-[1,1'-biphenyl]-2,2'-dicarboxamide

Refernces

• 1、 Akram, Manjur O.,Das, Avishek,Chakrabarty, Indradweep,Patil, Nitin T.. "Ligand-Enabled Gold-Catalyzed C(sp2)-N Cross-Coupling Reactions of Aryl Iodides with Amines". supporting information. p. 8101 - 8105. Retrieved 2019/10/11.
• 2、 Liu, Hailong,Han, Weibiao,Li, Chun,Ma, Zhiyong,Li, Ruixiang,Zheng, Xueli,Fu, Haiyan,Chen, Hua. "Practical Synthesis of Phenanthridinones by Palladium-Catalyzed One-Pot C-C and C-N Coupling Reaction: Extending the Substrate Scope to o-Chlorobenzamides". supporting information. p. 389 - 393. Retrieved 2016/02/18.