Benzenamine, N-phenyl-4-(phenylsulfonyl)-

Base Information

• Chemical Name: Benzenamine, N-phenyl-4-(phenylsulfonyl)-
• CAS No.: 61654-48-6
• Molecular Formula: C18H15NO2S
• Molecular Weight: 309.389
• DSSTox Substance ID: DTXSID50486698
• Nikkaji Number: J3.028.192F
• Wikidata: Q82328045
• Mol file: 61654-48-6.mol

Synonyms:Benzenamine, N-phenyl-4-(phenylsulfonyl)-;61654-48-6;DTXSID50486698

Chemical Property of Benzenamine, N-phenyl-4-(phenylsulfonyl)-

Chemical Property:

• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 309.08234989
• Heavy Atom Count: 22
• Complexity: 423

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)NC2=CC=C(C=C2)S(=O)(=O)C3=CC=CC=C3

Technology Process of Benzenamine, N-phenyl-4-(phenylsulfonyl)-

There total 6 articles about Benzenamine, N-phenyl-4-(phenylsulfonyl)- 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: 89.0%

4-Chlorophenyl phenyl sulfone (80-00-2,8012-45-1) + aniline (62-53-3) → N-phenyl-4-(phenylsulfonyl)benzenamine (61654-48-6)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; di(dicyclohexylamino)phenylphosphine; potassium tert-butylate; In toluene; for 4h; Reflux; Inert atmosphere;

DOI:10.1016/j.tet.2011.10.059

Reference yield: 54.0%

1-bromo-4-(phenylsulphonyl)benzene (23038-36-0) + aniline (62-53-3) → N-phenyl-4-(phenylsulfonyl)benzenamine (61654-48-6)

Guidance literature:

With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate; In toluene; at 90 - 110 ℃; for 18h; Inert atmosphere;

Reference yield:

1,4-bromoiodobenzene (589-87-7) → N-phenyl-4-(phenylsulfonyl)benzenamine (61654-48-6)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / dimethyl sulfoxide / 12 h / 120 °C

2: acetic acid; dihydrogen peroxide / 18 h / 100 °C

3: tri-tert-butyl phosphine; sodium t-butanolate; bis(dibenzylideneacetone)-palladium⁽⁰⁾ / toluene / 18 h / 90 - 110 °C / Inert atmosphere

With tri-tert-butyl phosphine; dihydrogen peroxide; potassium carbonate; acetic acid; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate; In dimethyl sulfoxide; toluene;

upstream raw materials:

4-Chlorophenyl phenyl sulfone

aniline

1,4-bromoiodobenzene

thiophenol

Refernces

• 1、 Kim, Bo Ram,Cho, Su-Dong,Kim, Eun Jung,Lee, In-Hye,Sung, Gi Hyeon,Kim, Jeum-Jong,Lee, Sang-Gyeong,Yoon, Yong-Jin. "Efficient palladium-catalyzed amination of aryl chlorides using di(dicyclohexylamino)phenylphosphine as a PN2 ligand". experimental part. p. 287 - 293. Retrieved 2012/01/05.