N-phenyl-4-(trifluoromethyl)aniline

Base Information

• Chemical Name: N-phenyl-4-(trifluoromethyl)aniline
• CAS No.: 53451-87-9
• Molecular Formula: C13H10F3N
• Molecular Weight: 237.224
• DSSTox Substance ID: DTXSID50457303
• Nikkaji Number: J2.073.431K
• Wikidata: Q82280106
• Mol file: 53451-87-9.mol

Synonyms:N-phenyl-4-(trifluoromethyl)aniline;14925-11-2;53451-87-9;Benzenamine, N-phenyl-4-(trifluoromethyl)-;SCHEMBL503225;4-(Trifluoromethyl)diphenylamine;DTXSID50457303;PCBLLVOSVHORQA-UHFFFAOYSA-N;SB80859

Chemical Property of N-phenyl-4-(trifluoromethyl)aniline

Chemical Property:

• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 237.07653381
• Heavy Atom Count: 17
• Complexity: 225

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)NC2=CC=C(C=C2)C(F)(F)F

Technology Process of N-phenyl-4-(trifluoromethyl)aniline

There total 29 articles about N-phenyl-4-(trifluoromethyl)aniline 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: 97.0%

p-trifluoromethylphenyl bromide (402-43-7) + aniline (62-53-3) → phenyl(4-trifluoromethylphenyl)amine (53451-87-9)

Guidance literature:

With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 2-(di-tert-butylphosphino)-1-(4-(triphenylsilyl)benzyl)benzimidazole; potassium tert-butylate; In toluene; Reagent/catalyst; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.jorganchem.2017.04.012

Reference yield: 96.0%

4-(trifluoromethyl)phenylsulfurofluoridate + aniline (62-53-3) → phenyl(4-trifluoromethylphenyl)amine (53451-87-9)

Guidance literature:

With η⁵‐cyclopentadienyl‐η³‐1‐phenylallylpalladium; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 80 ℃; for 12h; Reagent/catalyst; Temperature; Solvent;

DOI:10.1021/acscatal.6b00865

Reference yield: 90.0%

4-trifluoromethylphenylboronic acid (128796-39-4) + aniline (62-53-3) → phenyl(4-trifluoromethylphenyl)amine (53451-87-9)

Guidance literature:

With copper-exchanged fluorapatite; In methanol; at 20 ℃; for 4h;

DOI:10.1021/jo0614036

upstream raw materials:

N-phenyl-4-trifluoromethylacetanilide

aniline

4-oxo-3-(4-trifluoromethyl-phenyl)-3,4-dihydro-quinazoline-2-carboxylic acid ethyl ester

4-trifluoromethylphenylboronic acid

Downstream raw materials:

4-phenylaminobenzoic acid

3-(trifluoromethyl)-9H-carbazole

Refernces

• 1、 Nocera, Daniel G.,Qin, Yangzhong,Sun, Rui. "General Paradigm in Photoredox Nickel-Catalyzed Cross-Coupling Allows for Light-Free Access to Reactivity". supporting information. p. 9527 - 9533. Retrieved 2020/04/08.
• 2、 Akatyev, Nikolay,Il'in, Mikhail,Il'in, Mikhail,Peregudova, Svetlana,Peregudov, Alexander,Buyanovskaya, Anastasiya,Kudryavtsev, Kirill,Dubovik, Alexander,Grinberg, Valerij,Orlov, Victor,Pavlov, Alexander,Novikov, Valentin,Volkov, Ilya,Belokon, Yuri. "Chan-Evans-Lam C?N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle". . p. 3010 - 3021. Retrieved 2020/04/29.