169170-97-2

Basic information

• Product Name: (5-nitro-2-phenyl-benzoxazol-4-yl)acetonitrile
• Synonyms: (5-nitro-2-phenyl-benzoxazol-4-yl)acetonitrile
• CAS NO: 169170-97-2
• Molecular Weight: 279.255
• Mol File: 169170-97-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (5-nitro-2-phenyl-benzoxazol-4-yl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (5-nitro-2-phenyl-benzoxazol-4-yl)acetonitrile(169170-97-2)
• EPA Substance Registry System: (5-nitro-2-phenyl-benzoxazol-4-yl)acetonitrile(169170-97-2)

Safety Data

• Hazardous Substances Data: 169170-97-2(Hazardous Substances Data)

Upstream product

• 891-43-0 5-nitro-2-phenylbenzo[d]oxazole 
• 3598-13-8 (4-chlorophenoxy)acetonitrile 

Downstream Products

• 169170-98-3 2-phenyl-6H-pyrrolo<3,2-e>benzoxazole 

Relevant articles and documents

Synthesis of 1,3,4,5-Tetrahydropyrrolo-quinolines via the Vicarious Nucleophilic Substitution of Hydrogen

The VNS reaction was used as key steps in synthesis of O-methylnordehydrobufotenine and its 8-methoxy isomer starting from simple benzene derivatives.Attempts to use nitrobenzoxazole derivatives as a starting material were made.Several approaches were developed but all of them failed to produce the desired ring system on various stages of synthesis.

The vicarious nucleophilic substitution of hydrogen and related reactions in nitrobenzoxazoles

5- and 6-nitrobenzoxazoles 3 and 4 react with nucleophiles exclusively at C-2, giving ring opening products. If position 2- is blocked with phenyl substituent the reaction takes place in the carbocyclic ring affording the VNS products. 2-Methylthio-5-nitrobenzoxazole 7 and its 6-nitro isomer 8 give products which result from addition of a nucleophile to the carbocyclic ring (VNS) as well as to the heterocyclic ring (S(N)Ar and ring cleavage). 2-Methylthiobenzoxazoles can be readily converted to the corresponding benzoxazolones via oxidative hydrolysis.