4-(4-Chlorophenyl)benzonitrile

Base Information

• Chemical Name: 4-(4-Chlorophenyl)benzonitrile
• CAS No.: 57774-36-4
• Molecular Formula: C13H8ClN
• Molecular Weight: 213.666
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID50362746
• Nikkaji Number: J852.883G
• Wikidata: Q72517942
• Mol file: 57774-36-4.mol

Synonyms:57774-36-4;4-(4-chlorophenyl)benzonitrile;4'-chloro-4-cyanobiphenyl;4'-Chloro-[1,1'-biphenyl]-4-carbonitrile;4'-chlorobiphenyl-4-carbonitrile;SCHEMBL4446050;4-(4'-chlorophenyl)benzonitrile;DTXSID50362746;MFCD05980153;4-(4-chlorophenyl)benzenecarbonitrile;AKOS002683481;BS-28921;4'-chloro[1,1'-biphenyl]-4-carbonitrile;BB 0222994;CS-0192392;FT-0654704;E89814;A831595

Chemical Property of 4-(4-Chlorophenyl)benzonitrile

Chemical Property:

• Melting Point: 129-130 °C
• Boiling Point: 359.8 °C at 760 mmHg
• Flash Point: 156.4 °C
• PSA: 23.79000
• Density: 1.24 g/cm³
• LogP: 3.87868
• Storage Temp.: 2-8°C
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 213.0345270
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

99% ^*data from raw suppliers

4-(4-Chlorophenyl)benzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4-(4-Chlorophenyl)benzonitrile

There total 9 articles about 4-(4-Chlorophenyl)benzonitrile 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: 50.0%

1-Chloro-4-iodobenzene (637-87-6) + 4-iodobenzonitrile (3058-39-7) → (1,1'-biphenyl)-4,4'-dicarbonitrile (1591-30-6) + 4-(4'-chlorophenyl)benzonitrile (57774-36-4)

Guidance literature:

4-iodobenzonitrile; With lithium chloride; In N,N-dimethyl-formamide; at 80 ℃;

1-Chloro-4-iodobenzene; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 80 ℃; for 6h; Inert atmosphere;

DOI:10.1021/jo801074g

Reference yield:

benzonitrile (100-47-0) + aniline (62-53-3) → 4-(4'-chlorophenyl)benzonitrile (57774-36-4) + 4′-chloro-1,1′-biphenyl-2yl-carbonitrile (89346-58-7) + 4'-chloro-[1,1'-biphenyl]-3-carbonitrile (89346-59-8)

Guidance literature:

aniline; With hydrogenchloride; sodium nitrite; In water; at 0 ℃; for 0.583333h;

With sodium hydroxide; In water; at 80 ℃;

benzonitrile; Overall yield = 49 %; regioselective reaction;

DOI:10.1021/acs.joc.6b01840

Reference yield:

p-chlorobenzenediazonium tetrafluoroborate (673-41-6) + benzonitrile (100-47-0) → 4-(4'-chlorophenyl)benzonitrile (57774-36-4) + 4′-chloro-1,1′-biphenyl-2yl-carbonitrile (89346-58-7) + 4'-chloro-[1,1'-biphenyl]-3-carbonitrile (89346-59-8)

Guidance literature:

With potassium acetate; 18-crown-6 ether; for 1.5h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00183a021

upstream raw materials:

p-chlorobenzenediazonium tetrafluoroborate

benzonitrile

1-Chloro-4-iodobenzene

(4-cyanophenyl)trimethylstannane

Downstream raw materials:

(4'-chloro-[1,1'-biphenyl]-4-yl)methanamine

7-chloro-N-{(4′-chloro-[1,1′-biphenyl]-4-yl)methyl}-2-ethylimidazo[1,2-a]pyridine-3-carboxamide

6-chloro-N-{(4'-chloro-[1,1'-biphenyl]-4-yl)methyl}-2-ethylimidazo[1,2-a]pyridine-3-carboxamide

4'-chlorobiphenyl-4-carboxylic acid

Refernces

• 1、 Yu, Peng,Morandi, Bill. "Nickel-Catalyzed Cyanation of Aryl Chlorides and Triflates Using Butyronitrile: Merging Retro-hydrocyanation with Cross-Coupling". . p. 15693 - 15697. Retrieved 2017/12/02.
• 2、 Chauhan, Parul,Ravi, Makthala,Singh, Shikha,Raju, Kanumuri S. R.,Bajpai, Vikas,Kumar, Brijesh,Wahajuddin,Yadav, Prem. P.. "Palladium and copper-catalyzed ligand-free coupling of phenylhydrazines in water". . p. 43336 - 43340. Retrieved 2015/02/19.