N,3,5-trimethylbenzamide

Base Information

• Chemical Name: N,3,5-trimethylbenzamide
• CAS No.: 172369-18-5
• Molecular Formula: C10H13NO
• Molecular Weight: 163.21600
• DSSTox Substance ID: DTXSID70358742
• Nikkaji Number: J845.940A
• Wikidata: Q82139559
• Mol file: 172369-18-5.mol

Synonyms:N,3,5-trimethylbenzamide;172369-18-5;Benzamide, N,3,5-trimethyl- (9CI);SCHEMBL1003295;DTXSID70358742;AKOS008933412;CS-0293896;Z32016578

Chemical Property of N,3,5-trimethylbenzamide

Chemical Property:

• PSA: 32.59000
• LogP: 2.23780
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 163.099714038
• Heavy Atom Count: 12
• Complexity: 157

Purity/Quality:

99% ^*data from raw suppliers

N,3,5-TRIMETHYL-BENZAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of N,3,5-trimethylbenzamide

There total 6 articles about N,3,5-trimethylbenzamide 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: 83.0%

methanol (67-56-1) + 3,5-dimethylbenzamide (5692-35-3) → N,3,5-trimethylbenzamide (172369-18-5)

Guidance literature:

With C₅₄H₄₃ClN₃P₂Ru⁽¹⁺⁾*F₆P^(1-); caesium carbonate; In toluene; at 140 ℃; for 36h; Inert atmosphere; Sealed tube; Green chemistry;

DOI:10.1021/acs.orglett.9b01925

Reference yield: 72.0%

4-iodo-N,3-dimethylbenzamide + methyl p-toluene sulfonate (80-48-8) → N,3,5-trimethylbenzamide (172369-18-5)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2-o-tolyl-3a,4,7,7a-tetrahydro-4,7-methano-isoindole-1,3-dione; trifuran-2-yl-phosphane; sodium formate; caesium carbonate; In 1,2-dimethoxyethane; at 80 ℃; for 15h; Inert atmosphere;

DOI:10.1021/jacs.9b07857

Reference yield: 61.0%

methylamine hydrochloride (593-51-1) + 3,5-dimethylbenzoyl chloride (6613-44-1) → N,3,5-trimethylbenzamide (172369-18-5)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 25 ℃;

DOI:10.1021/acs.orglett.7b02778

upstream raw materials:

Methyl fluorosulfonate

3,5-dimethylbenzonitrile

3,5-dimethylbenzoic acid

methylamine hydrochloride

Downstream raw materials:

3,5-dimethylbenzophenone

Refernces

• 1、 Paul, Bhaskar,Panja, Dibyajyoti,Kundu, Sabuj. "Ruthenium-Catalyzed Synthesis of N-Methylated Amides using Methanol". supporting information. p. 5843 - 5847. Retrieved 2019/08/26.
• 2、 Gao, Qianwen,Shang, Yong,Song, Fuzhen,Ye, Jinxiang,Liu, Ze-Shui,Li, Lisha,Cheng, Hong-Gang,Zhou, Qianghui. "Modular Dual-Tasked C-H Methylation via the Catellani Strategy". supporting information. p. 15986 - 15993. Retrieved 2019/10/11.