127703-35-9

Basic information

• Product Name: 2-(4-Cyanophenyl)phenol
• Synonyms: 2-(4-Cyanophenyl)phenol
• CAS NO: 127703-35-9
• Molecular Formula: C₁₃H₉NO
• Molecular Weight: 195.21666
• Mol File: 127703-35-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-Cyanophenyl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Cyanophenyl)phenol(127703-35-9)
• EPA Substance Registry System: 2-(4-Cyanophenyl)phenol(127703-35-9)

Safety Data

• Hazardous Substances Data: 127703-35-9(Hazardous Substances Data)

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 139-02-6 sodium phenoxide 
• 111278-47-8 C₁₃H₉N₃S 
• 16909-23-2 tetra-n-butylammonium phenolate 
• 29577-88-6 (Z)-tert-Butyl (4-cyanophenyl)azo sulfide 
• 108-95-2 phenol 
• 132555-11-4 (E)-(4-Cyanophenyl)azo phenyl sulfide 
• 3096-81-9 4-phenoxybenzonitrile 

Relevant articles and documents

A new cascade radical reaction for the synthesis of biaryls and triaryls from benzyl iodoaryl ethers

The paper describes a new method of synthesizing biaryls and triaryls through an intramolecular ipso-substitution reaction initiated by the addition of an aryl radical to a benzyl ether. A tandem variant of the reaction has also been demonstrated. A short synthesis of isoaucuparin 27, a natural product found in the sapwood tissue of Sorbus aucuparia, is also described.

SRN1C-arylation of potassium aryloxides by arylazo phenyl or tert- butyl sulfides in DMSO

Aryloxide ions (Ar′O-) behave as C-nucleophiles towards diazosulfides (ArN = NSR; R = Ph, But) leading to imsymmetrical hydroxybiaryls (ArAr′OH) via C-C coupling. The reaction is particularly suited for the synthesis of terms which contain electron-withdrawing groups on the Ar moiety. The SRN1 mechanism is proposed on the grounds of experimental evidences.

Electrochemically Catalyzed Aromatic Nucleophilic Substitution. Phenoxide Ion as Nucleophile

Cyclic voltammetry and preparative-scale electrolysis of aryl halides in the presence of phenoxide ions, a nucleophile reputed as unreactive SRN1 reactions, show the formation, in liquid ammonia or in dimethyl sulfoxide, of coupling products along an electrochemically catalyzed SRN1 aromatic substitution process.Coupling occurs at carbons of the phenyl ring rather than at the phenolic oxygen.The mechanism of the reaction is estabilished on kinetic grounds.Determination of the coupling rate constant between phenoxide ions and aryl radicals and comparison with other n ucleophiles shows that phenoxide ions are quite efficient nucleophiles in SRN1 reactions.The reaction can as well be viewed as an homolytic aromatic substitution.Mechanistic implications concerning the latter type of reaction are discussed.With mediated electrochemical induction of the substitution reaction, it is possible to raise the yield in coupling product up to about 80percent, which renders the reaction an attractive route to the synthesis of electron donor-electron acceptor biaryls.