Bis(P-chlorophenyl)acetonitrile

Base Information

• Chemical Name: Bis(P-chlorophenyl)acetonitrile
• CAS No.: 20968-04-1
• Molecular Formula: C14H9Cl2N
• Molecular Weight: 262.138
• DSSTox Substance ID: DTXSID80175144
• Nikkaji Number: J630.129K
• Wikidata: Q83045399
• Mol file: 20968-04-1.mol

Synonyms:bis(p-chlorophenyl)acetonitrile;p,p'-DDCN

Chemical Property of Bis(P-chlorophenyl)acetonitrile

Chemical Property:

• Vapor Pressure: 5.75E-06mmHg at 25°C
• Boiling Point: 379.7°Cat760mmHg
• Flash Point: 155.9°C
• PSA: 23.79000
• Density: 1.288g/cm³
• LogP: 4.64888
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 261.0112047
• Heavy Atom Count: 17
• Complexity: 258

Purity/Quality:

97% ^*data from raw suppliers

2,2-Bis(4-chlorophenyl)acetonitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(C#N)C2=CC=C(C=C2)Cl)Cl

Technology Process of Bis(P-chlorophenyl)acetonitrile

There total 12 articles about Bis(P-chlorophenyl)acetonitrile 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: 91.0%

trimethylsilyl cyanide (7677-24-9) + 4,4'-dichlorobenzophenone (90-97-1) → 2,2’-bis(4-(chloro)phenyl)acetonitrile (20968-04-1)

Guidance literature:

With tris(pentafluorophenyl)borate; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2009.03.073

Reference yield: 38.0%

bis(4-chlorophenyl)(cyano)methyl diethyl phosphate + 1-cyanocyclohexyl methanesulfonate (195370-95-7) → 2,2’-bis(4-(chloro)phenyl)acetonitrile (20968-04-1) + tetrakis-(4-chloro-phenyl)-succinonitrile (103037-17-8)

Guidance literature:

With [(C₅H₅)2TiI]; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.joc.1c02643

Reference yield:

bis(4'-chlorophenyl)acetic acid (83-05-6) → 2,2’-bis(4-(chloro)phenyl)acetonitrile (20968-04-1)

Guidance literature:

Multi-step reaction with 2 steps

2: POCl₃

With trichlorophosphate;

upstream raw materials:

2,2-bis-(4-chloro-phenyl)acetamide

acetic anhydride

bis(4'-chlorophenyl)acetic acid

2,2-bis(4-chlorophenyl)acetyl chloride

Downstream raw materials:

C₂₅H₂₃Cl₂NO₂S

2-(4,4'-dichloro-benzhydryl)-piperidine

2-(4,4'-dichloro-benzhydryl)-1-methyl-piperidine

2-(4,4'-dichloro-benzhydryl)-pyridine

Refernces

• 1、 Casavant, Barbara J.,Hosseini, Azade S.,Chemler, Sherry R.. "6-azabicyclo[3.2.1]octanes via copper-catalyzed enantioselective alkene carboamination". supporting information. p. 2697 - 2702. Retrieved 2014/09/29.
• 2、 Mori, Keiji,Sueoka, Shosaku,Akiyama, Takahiko. "Dual functionalization of allene: facile construction of heteropolycycles mediated by Bronsted acid". supporting information; experimental part. p. 628 - 629. Retrieved 2011/04/22.