p-Isobutyrotoluidide

Base Information

• Chemical Name: p-Isobutyrotoluidide
• CAS No.: 6876-49-9
• Molecular Formula: C11H15 N O
• Molecular Weight: 177.246
• Hs Code.: 2924299090
• NSC Number: 401965,401126
• DSSTox Substance ID: DTXSID40218869
• Nikkaji Number: J3.037.938A
• Wikidata: Q83095786
• Mol file: 6876-49-9.mol

Synonyms:p-Isobutyrotoluidide;6876-49-9;2-methyl-N-(4-methylphenyl)propanamide;NSC401965;ChemDiv2_000207;SCHEMBL178429;DTXSID40218869;HMS1369J09;NSC401126;AKOS001572885;NSC 401126;NSC 401965;NSC-401126;NSC-401965;EU-0068144;SR-01000400086;SR-01000400086-1

Chemical Property of p-Isobutyrotoluidide

Chemical Property:

• Vapor Pressure: 0.000232mmHg at 25°C
• Boiling Point: 325.3°C at 760 mmHg
• Flash Point: 192.1°C
• PSA: 29.10000
• Density: 1.029g/cm³
• LogP: 2.66250
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 177.115364102
• Heavy Atom Count: 13
• Complexity: 169

Purity/Quality:

99% ^*data from raw suppliers

2-METHYL-N-(4-METHYLPHENYL)PROPANAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of p-Isobutyrotoluidide

There total 22 articles about p-Isobutyrotoluidide 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: 90.0%

p-toluidine (106-49-0,12221-03-3) + Ethyl isobutyrate (97-62-1) → N-(4-methylphenyl)-2,2-dimethylacetamide (6876-49-9)

Guidance literature:

With potassium tert-butylate; water; oxygen; In tetrahydrofuran; at 20 ℃; for 0.166667h;

DOI:10.1055/s-0031-1289622

Reference yield: 88.0%

2,N-dimethyl-N-phenylpropanamide (55577-65-6) + p-toluidine (106-49-0,12221-03-3) → N-(4-methylphenyl)-2,2-dimethylacetamide (6876-49-9)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; toluene; at 23 ℃; for 15h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/jacs.9b04136

Reference yield: 86.0%

N-(4-bromophenyl)isobutyramide (7160-08-9) + methyl p-toluene sulfonate (80-48-8) → N-(4-methylphenyl)-2,2-dimethylacetamide (6876-49-9)

Guidance literature:

With nickel(II) iodide; 4,4'-dimethyl-2,2'-bipyridines; tetra-(n-butyl)ammonium iodide; magnesium chloride; zinc; In N,N-dimethyl acetamide; at 20 ℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1039/c7cc06106d

upstream raw materials:

p-toluidine

isobutyryl chloride

isobutyric Acid

2-methyl-2-(triphenylphosphonio)dithiopropionate betaine

Downstream raw materials:

dimethylketene-N-p-tolylimine

[1-Benzotriazol-1-yl-2-methyl-prop-(E)-ylidene]-p-tolyl-amine

N-p-tolyl-isobutyrimidoyl chloride

Refernces

• 1、 Joseph, Devaneyan,Lee, Sunwoo,Park, Myeong Seong. "Metal-free transamidation of benzoylpyrrolidin-2-one and amines under aqueous conditions". supporting information. p. 6227 - 6232. Retrieved 2021/07/28.
• 2、 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.