N-(oxiran-2-ylmethyl)-N-phenylaniline

Base Information

• Chemical Name: N-(oxiran-2-ylmethyl)-N-phenylaniline
• CAS No.: 4510-27-4
• Molecular Formula: C15H15NO
• Molecular Weight: 225.29
• DSSTox Substance ID: DTXSID50392982
• Nikkaji Number: J2.061.373D
• Mol file: 4510-27-4.mol

Synonyms:N-(oxiran-2-ylmethyl)-N-phenylaniline;4510-27-4;N-Glycidyldiphenylamine;SCHEMBL9866782;DTXSID50392982;N-(2,3-epoxypropyl)diphenylamine;STL563387;AKOS015955307

Chemical Property of N-(oxiran-2-ylmethyl)-N-phenylaniline

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 225.115364102
• Heavy Atom Count: 17
• Complexity: 213

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)CN(C2=CC=CC=C2)C3=CC=CC=C3

Technology Process of N-(oxiran-2-ylmethyl)-N-phenylaniline

There total 6 articles about N-(oxiran-2-ylmethyl)-N-phenylaniline 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: 91.5%

diphenylamine (122-39-4) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → N-(oxiran-2-ylmethyl)-N-phenylaniline (4510-27-4)

Guidance literature:

With potassium hydroxide; potassium carbonate; for 7h;

DOI:10.1007/s10593-007-0117-7

Reference yield: 57.0%

N-(2,3-dihydroxypropyl)diphenylamine (168611-98-1) → N-(oxiran-2-ylmethyl)-N-phenylaniline (4510-27-4)

Guidance literature:

With p-toluenesulfonylanhydride; sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃;

DOI:10.1021/ol801860s

Reference yield:

diphenylamine (122-39-4) + 1,2-Epoxy-3-bromopropane (3132-64-7,82584-73-4) → N-(oxiran-2-ylmethyl)-N-phenylaniline (4510-27-4)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 15h;

DOI:10.1016/j.bmcl.2008.07.006

upstream raw materials:

N-(γ-Chlor-β-hydroxypropyl)diphenylamin

diphenylamine

epichlorohydrin

1,2-Epoxy-3-bromopropane

Downstream raw materials:

N-(2,3-dihydroxypropyl)diphenylamine

1-phenyl-1,2,3,4-tetrahydroquinoline

3-hydroxy-1-phenyl-1,2,3,4-tetrahydroquinoline

[2-(4-Bromo-phenyl)-2-oxo-ethyl]-((S)-3-diphenylamino-2-hydroxy-propyl)-dimethyl-ammonium; bromide

Refernces

• 1、 MacIejewski, John P.,Wipf, Peter. "Titanocene(III)-catalyzed conversion of N-(epoxyalkyl)anilines into indolines". experimental part. p. 92 - 119. Retrieved 2011/06/20.
• 2、 Wipf, Peter,Maciejewski, John P.. "Titanocene(III)-catalyzed formation of indolines and azaindolines". supporting information; experimental part. p. 4383 - 4386. Retrieved 2009/05/30.