Benzenamine, N-(1H-indol-3-ylmethylene)-4-methyl-

Base Information

• Chemical Name: Benzenamine, N-(1H-indol-3-ylmethylene)-4-methyl-
• CAS No.: 105850-59-7
• Molecular Formula: C16H14N2
• Molecular Weight: 234.301
• DSSTox Substance ID: DTXSID10425306
• ChEMBL ID: CHEMBL1957878
• Mol file: 105850-59-7.mol

Synonyms:CHEMBL1957878;Benzenamine, N-(1H-indol-3-ylmethylene)-4-methyl-;105850-59-7;CBDivE_003053;SCHEMBL18463068;DTXSID10425306;BDBM50365893;STL299993;AKOS022129908;3-[(4-Methylphenylimino)Methyl]Indole;(1H-Indol-3-ylmethylene)(4-methylphenyl)amine;N-[(E)-1H-indol-3-ylmethylidene]-4-methylaniline

Chemical Property of Benzenamine, N-(1H-indol-3-ylmethylene)-4-methyl-

Chemical Property:

• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 234.115698455
• Heavy Atom Count: 18
• Complexity: 292

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)N=CC2=CNC3=CC=CC=C32

Technology Process of Benzenamine, N-(1H-indol-3-ylmethylene)-4-methyl-

There total 2 articles about Benzenamine, N-(1H-indol-3-ylmethylene)-4-methyl- 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: 78.0%

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) + p-toluidine (106-49-0,12221-03-3) → 3-[(4-methylphenylimino)methyl]indole (105850-59-7)

Guidance literature:

Indole-3-carboxaldehyde; With toluene-4-sulfonic acid; In ethanol; at 70 - 80 ℃; for 0.25h;

p-toluidine; In ethanol; for 4h; Reflux;

DOI:10.1016/j.bmcl.2012.01.130

Reference yield:

indole (120-72-9) → 3-[(4-methylphenylimino)methyl]indole (105850-59-7)

Guidance literature:

Multi-step reaction with 2 steps

1: trichlorophosphate

2: acetic acid / ethanol / Reflux; Molecular sieve

With acetic acid; trichlorophosphate; In ethanol; 1: |Vilsmeier-Haack Formylation;

DOI:10.1002/ardp.201400148

Reference yield: 69.0%

3-[(4-methylphenylimino)methyl]indole (105850-59-7) + mercaptoacetic acid (68-11-1) → 2-(1H-indol-3-yl)-3-(p-tolyl)thiazolidin-4-one

Guidance literature:

With zinc(II) chloride; In N,N-dimethyl-formamide; at 90 ℃; for 1 - 1.5h; Sonication;

DOI:10.1002/ardp.201400148

upstream raw materials:

Indole-3-carboxaldehyde

p-toluidine

indole