N-(2-Bromo-4-methylphenyl)-N-methylacetamide

Base Information

• Chemical Name: N-(2-Bromo-4-methylphenyl)-N-methylacetamide
• CAS No.: 87995-51-5
• Molecular Formula: C10H12BrNO
• Molecular Weight: 242.115
• DSSTox Substance ID: DTXSID80522932
• Wikidata: Q82388637
• Mol file: 87995-51-5.mol

Synonyms:N-(2-Bromo-4-methylphenyl)-N-methylacetamide;87995-51-5;DTXSID80522932

Chemical Property of N-(2-Bromo-4-methylphenyl)-N-methylacetamide

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 241.01023
• Heavy Atom Count: 13
• Complexity: 195

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1)N(C)C(=O)C)Br

Technology Process of N-(2-Bromo-4-methylphenyl)-N-methylacetamide

There total 4 articles about N-(2-Bromo-4-methylphenyl)-N-methylacetamide 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: 91.0%

2-bromo-4-methylacetanilide (614-83-5) + dimethyl sulfate (77-78-1) → N-(2-bromo-4-methylphenyl)-N-methylacetamide (87995-51-5)

Guidance literature:

phase transfer procedure;

Reference yield: 80.0%

4-(N-methylacetamido)toluene (612-03-3) → N-(2-bromo-4-methylphenyl)-N-methylacetamide (87995-51-5)

Guidance literature:

With N-Bromosuccinimide; trityl tetrafluoroborate; In dichloromethane; acetonitrile; at 20 ℃; chemoselective reaction; Inert atmosphere;

DOI:10.1002/adsc.201800788

Reference yield:

2-bromo-p-toluidine (583-68-6) → N-(2-bromo-4-methylphenyl)-N-methylacetamide (87995-51-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / tetrahydrofuran / 0.67 h / 0 - 20 °C

2.1: sodium hydride / tetrahydrofuran / 0.67 h / 0 °C

2.2: 0 - 20 °C

With sodium hydride; triethylamine; In tetrahydrofuran;

DOI:10.1016/j.mcat.2022.112211

upstream raw materials:

2-bromo-4-methylacetanilide

dimethyl sulfate

4-(N-methylacetamido)toluene

2-bromo-p-toluidine

Downstream raw materials:

2-bromo-4-methyl-N-methylaniline

(E)-N,4-Dimethyl-2-<(4-methylphenyl)(4-methylphenylimino)methyl>anilin

(Z)-N,4-Dimethyl-2-<(4-methylphenyl)(4-methylphenylimino)methyl>anilin

N¹-(2-Brom-4-methylphenyl)-N¹,4-dimethyl-N²-(4-methylphenyl)benzamidin

Refernces

• 1、 Anastasiou, Ioannis,Chen, Shaomin,Ferlin, Francesco,Gu, Yanglong,Liu, Ping,Minio, Francesco,Salameh, Nihad,Santoro, Stefano,Vaccaro, Luigi. "Heterogeneous palladium-catalysed intramolecular C(sp3)[sbnd]H α-arylation for the green synthesis of oxindoles". . . Retrieved 2022/03/27.
• 2、 Hellwinkel, Dieter,Laemmerzahl, Frank,Hofmann, Gunter. "Carbanionically Induced -Migrations of ?- and Coordinatively Unsaturated Groups". . p. 3375 - 3405. Retrieved 2007/10/02.