N,N-Bis[2-(tosyloxy)ethyl]aniline

Base Information

• Chemical Name: N,N-Bis[2-(tosyloxy)ethyl]aniline
• CAS No.: 3590-12-3
• Molecular Formula: C24H27NO6S2
• Molecular Weight: 489.613
• NSC Number: 75326
• DSSTox Substance ID: DTXSID40957322
• Nikkaji Number: J1.529.957F
• Wikidata: Q82937633
• ChEMBL ID: CHEMBL3247497
• Mol file: 3590-12-3.mol

Synonyms:NIOSH/KM2160000;KM21600000;2-(Phenylimino)diethanol di-p-toluenesulfonate;Ethanol, 2-(phenylimino)di-, di-p-toluenesulfonate;Benzenesulfonic acid, p-methyl-, (phenylimino)diethylene ester;3590-12-3;NSC75326;CHEMBL3247497;DTXSID40957322;CATMAHFPKNTCAA-UHFFFAOYSA-N;NSC-75326;Ethanol,2'-(phenylimino)di-, di-p-toluenesulfonate (ester);(phenylimino)diethane-2,1-diyl bis(4-methylbenzenesulfonate);Ethanol,2'-(phenylimino)bis-, bis(4-methylbenzenesulfonate) (ester);(Phenylazanediyl)di(ethane-2,1-diyl) bis(4-methylbenzene-1-sulfonate);Ethanol, 2,2'-(phenylimino)bis-, bis(4-methylbenzenesulfonate) (ester)

Chemical Property of N,N-Bis[2-(tosyloxy)ethyl]aniline

Chemical Property:

• Vapor Pressure: 1.87E-17mmHg at 25°C
• Boiling Point: 663.1°Cat760mmHg
• Flash Point: 354.8°C
• Density: 1.295g/cm³
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 489.12797993
• Heavy Atom Count: 33
• Complexity: 709

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCCN(CCOS(=O)(=O)C2=CC=C(C=C2)C)C3=CC=CC=C3

Technology Process of N,N-Bis[2-(tosyloxy)ethyl]aniline

There total 4 articles about N,N-Bis[2-(tosyloxy)ethyl]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: 92.0%

2,2'-(phenylimino)bis[ethanol] (120-07-0) + p-toluenesulfonyl chloride (98-59-9) → N,N-bis(2-p-tolylsulfonyloxyethyl)aniline (3590-12-3)

Guidance literature:

With pyridine; at 0 - 5 ℃; for 24.5h;

DOI:10.1007/s10847-012-0219-4

Reference yield: 80.0%

2,2'-(phenylimino)bis[ethanol] (120-07-0) → N,N-bis(2-p-tolylsulfonyloxyethyl)aniline (3590-12-3)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; at 0 - 5 ℃;

DOI:10.1080/10610278.2011.575469

Reference yield:

phenyliminodiacetic acid diethyl ester (55932-12-2) → N,N-bis(2-p-tolylsulfonyloxyethyl)aniline (3590-12-3)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / tetrahydrofuran / 2 h / 80 °C

2: 85 percent / pyridine / 5 h / cooling

With pyridine; lithium aluminium tetrahydride; In tetrahydrofuran;

DOI:10.1016/j.tet.2006.06.035

upstream raw materials:

2,2'-(phenylimino)bis[ethanol]

p-toluenesulfonyl chloride

phenyliminodiacetic acid diethyl ester

aniline

Downstream raw materials:

4-phenyl-1-thia-4-azacyclohexane

1-Phenyl-4,7,10-tris-(toluene-4-sulfonyl)-1,4,7,10-tetraaza-cyclododecane

C₁₆H₂₃NO₄S₂