(2S)-2-(4-chloroanilino)-2-phenylpropanenitrile

Base Information

• Chemical Name: (2S)-2-(4-chloroanilino)-2-phenylpropanenitrile
• CAS No.: 81512-04-1
• Molecular Formula: C15H13ClN2
• Molecular Weight: 256.735
• DSSTox Substance ID: DTXSID101002020
• Wikidata: Q82996053
• Mol file: 81512-04-1.mol

Synonyms:2-(4-chloroanilino)-2-phenylpropanenitrile;DTXSID101002020;81512-04-1

Chemical Property of (2S)-2-(4-chloroanilino)-2-phenylpropanenitrile

Chemical Property:

• Vapor Pressure: 2.46E-07mmHg at 25°C
• Boiling Point: 422.2°C at 760 mmHg
• Flash Point: 209.1°C
• Density: 1.229g/cm³
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 256.0767261
• Heavy Atom Count: 18
• Complexity: 308

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C#N)(C1=CC=CC=C1)NC2=CC=C(C=C2)Cl
• Isomeric SMILES: C[C@@](C#N)(C1=CC=CC=C1)NC2=CC=C(C=C2)Cl

Technology Process of (2S)-2-(4-chloroanilino)-2-phenylpropanenitrile

There total 7 articles about (2S)-2-(4-chloroanilino)-2-phenylpropanenitrile 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: 95.0%

trimethylsilyl cyanide (7677-24-9) + 4-chloro-aniline (106-47-8) + acetophenone (98-86-2) → α-(p-chloroanilino)-α-phenylpropionitrile (81512-04-1)

Guidance literature:

With Sn-Montmorillonite; at 25 ℃; for 0.75h; Neat (no solvent);

DOI:10.1002/ejoc.200901323

Reference yield: 94.0%

trimethylsilyl cyanide (7677-24-9) + 4-chloro-aniline (106-47-8) + phenylacetylene (536-74-3) → α-(p-chloroanilino)-α-phenylpropionitrile (81512-04-1)

Guidance literature:

4-chloro-aniline; phenylacetylene; With indium(III) bromide; In toluene; at 110 ℃; for 6h; Sealed tube; Inert atmosphere; Reflux;

trimethylsilyl cyanide; In toluene; at 80 ℃; for 21h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.6b00508

Reference yield: 85.0%

2-hydroxy-2-phenylpropionitrile (20102-12-9) + 4-chloro-aniline (106-47-8) → α-(p-chloroanilino)-α-phenylpropionitrile (81512-04-1)

Guidance literature:

In ethanol;

upstream raw materials:

2-hydroxy-2-phenylpropionitrile

4-chloro-aniline

potassium cyanide

acetophenone

Downstream raw materials:

6-(4-chlorophenyl)-4-hydroxy-7-phenyl-pyrano[3,2-c]pyridine-2,5(6H)-dione

3-acetyl-1-(4-chlorophenyl)-4-hydroxy-6-phenyl-pyridin-2(1H)-one

N-(1-phenylethylidene)-4-chloroaniline

3-(p-chlorophenyl)-5-imino-4-methyl-1,4-diphenyl-imidazolidin-2-one

Refernces

• 1、 Eidi, Esmaiel,Kassaee, Mohamad Z.,Nasresfahani, Zahra,Cummings, Peter T.. "Gallic acid-functionalized magnetic nanoparticles: a convenient and green approach for synthesis of α-aminonitriles under solvent-free conditions". . p. 303 - 314. Retrieved 2018/10/15.
• 2、 Nammalwar, Baskar,Fortenberry, Chelsea,Bunce, Richard A.. "Synthesis of α-aminonitriles under mild catalytic, metal-free conditions". supporting information. p. 379 - 381. Retrieved 2014/01/06.