N-(4-Methylphenyl)benzamide

Base Information

• Chemical Name: N-(4-Methylphenyl)benzamide
• CAS No.: 582-78-5
• Molecular Formula: C14H13NO
• Molecular Weight: 211.263
• Hs Code.: 2924299090
• European Community (EC) Number: 209-491-8
• NSC Number: 17586
• DSSTox Substance ID: DTXSID20206946
• Nikkaji Number: J7.440C
• Wikidata: Q83080844
• ChEMBL ID: CHEMBL1489271
• Mol file: 582-78-5.mol

Synonyms:N-(4-Methylphenyl)benzamide;582-78-5;p-Benzotoluidide;N-p-Tolyl-benzamide;4'-Methylbenzanilide;BENZO-p-TOLUIDIDE;Benzamide, N-(4-methylphenyl)-;N-(p-tolyl)benzamide;Benzamide, N-p-tolyl-;p-Toluoylaniline;N-Benzoyl-p-toluidine;Benzoic acid p-toluidide;EINECS 209-491-8;AI3-00503;Benz-p-toluidid;N-p-tolylbenzamide;Para-methylbenzanilide;4/'-Methylbenzanilide;Maybridge1_004370;SCHEMBL82305;MLS000523601;N-(4-Methylphenyl)benzamide #;CHEMBL1489271;HMS553O16;DTXSID20206946;HMS2359E23;NSC17586;NSC-17586;STK259692;AKOS000277999;NCGC00245386-01;AS-84016;SMR000122674;CS-0246372;E77739;EN300-322954;AE-848/00895014;SR-01000414618;SR-01000414618-1;Z28134753

Chemical Property of N-(4-Methylphenyl)benzamide

Chemical Property:

• Melting Point: 158 °C
• Refractive Index: 1.5780 (estimate)
• Boiling Point: 265.3 °C at 760 mmHg
• PKA: 13.52±0.70(Predicted)
• Flash Point: 154.9 °C
• PSA: 29.10000
• Density: 1.144 g/cm³
• LogP: 3.32030
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 211.099714038
• Heavy Atom Count: 16
• Complexity: 225

Purity/Quality:

99% ^*data from raw suppliers

N-(4-methylphenyl)benzamide ^*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)C2=CC=CC=C2
• Uses: N-(4-methylphenyl)benzamide is prepared through copper-catalyzed amidation of aryl halides and N-arylation of heterocycles with aryl halides using cyclohexanediamine ligands. It is used as a reactant in preparation of 2-arylbenzoxazoles by copper-catalyzed regioselective intramolecular oxidative C-O coupling of benzanilides.

Technology Process of N-(4-Methylphenyl)benzamide

There total 301 articles about N-(4-Methylphenyl)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: 98.0%

benzaldehyde (100-52-7) + p-toluidine (106-49-0,12221-03-3) → N-(4-methylphenyl)benzamide (582-78-5) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

p-toluidine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

benzaldehyde; With yttrium(III) chloride; In toluene; at 20 ℃; for 48h; Inert atmosphere;

With hydrogenchloride; In water; toluene; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.09.101

Reference yield: 98.0%

phenyl benzyl ketone (451-40-1) + p-toluidine (106-49-0,12221-03-3) → N-(4-methylphenyl)benzamide (582-78-5) + benzaldehyde (100-52-7)

Guidance literature:

With 1,10-Phenanthroline; copper(II) chloride dihydrate; oxygen; In acetonitrile; for 48h; under 760.051 Torr; Reflux;

DOI:10.1021/acs.joc.5b01670

Reference yield: 97.0%

N-(4-methylphenyl)benzamidine (1859-00-3) + benzil (134-81-6) → N-benzoylbenzamide (614-28-8) + N-(4-methylphenyl)benzamide (582-78-5)

Guidance literature:

With vanadyl(IV) sulfate hydrate; water; In N,N-dimethyl-formamide; at 70 ℃; for 18h;

DOI:10.1021/acs.joc.7b00950

upstream raw materials:

pentan-1-ol

N-benzoyl-N,N'-di-p-tolyl-urea

4-Methylbenzophenone

(Z)-phenyl(p-tolyl)methanone oxime

Downstream raw materials:

(Benzoyl-p-tolyl-amino)-acetic acid ethyl ester

N-(2-chloro-4-methylphenyl)benzamide

p-benzamidobenzoic acid

N-benzyl-N-(4-methylphenyl)amine

Refernces

• 1、 Wang, Yi-Jie,Zhang, Guo-Yu,Shoberu, Adedamola,Zou, Jian-Ping. "Iron-catalyzed oxidative amidation of acylhydrazines with amines". supporting information. . Retrieved 2021/08/18.
• 2、 Li, Jinhui,Liu, Jin-Biao,Luo, Nianhua,Qiu, Guanyinsheng,Ren, Shangfeng,Wang, Ying,Xie, Huilin. "Iron-catalyzed cross-coupling of N?methoxy amides and arylboronic acids for the synthesis of N-aryl amides". . . Retrieved 2021/11/11.