28353-03-9

Basic information

• Product Name: 6-OXO-6-PHENYLHEXANENITRILE
• Synonyms: 6-OXO-6-PHENYLHEXANENITRILE
• CAS NO: 28353-03-9
• Molecular Formula: C₁₂H₁₃NO
• Molecular Weight: 187.24
• Mol File: 28353-03-9.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 360.8°C at 760 mmHg
• Flash Point: 172°C
• Appearance: /
• Density: 1.038g/cm³
• Vapor Pressure: 2.16E-05mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: 6-OXO-6-PHENYLHEXANENITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-OXO-6-PHENYLHEXANENITRILE(28353-03-9)
• EPA Substance Registry System: 6-OXO-6-PHENYLHEXANENITRILE(28353-03-9)

Safety Data

• Hazardous Substances Data: 28353-03-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H13NO/c13-10-6-2-5-9-12(14)11-7-3-1-4-8-11/h1,3-4,7-8H,2,5-6,9H2

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 20614-62-4 (1-hydroperoxycyclopentyl)benzene 
• 10487-96-4 1-phenylcyclopentanol 
• 16717-64-9 1-azidostyrene 
• 5332-06-9 4-bromobutanenitrile 
• 827-52-1 1-phenyl-1-cyclohexane 
• 20614-61-3 cyclohexyl-1-phenyl-1-hydroperoxide 
• 1624363-23-0 3-azido-2-methylbut-3-en-2-ol 
• 108-94-1 cyclohexanone 
• 108-86-1 bromobenzene 
• 100-42-5 styrene 
• 22591-17-9 2-phenylcyclohexanone oxime 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 13735-81-4 1-styrenyloxytrimethylsilane 

Downstream Products

• 4829-02-1 (S)-(+)-2-hydroxy-2-phenylcyclohexanone 
• 4829-02-1 2-hydroxy-2-phenylcyclohexanone 

Relevant articles and documents

The Formation of C-C or C-N Bonds via the Copper-Catalyzed Coupling of Alkylsilyl Peroxides and Organosilicon Compounds: A Route to Perfluoroalkylation

The copper-catalyzed selective cleavage of alkylsilyl peroxides and the subsequent formation of carbon-carbon or carbon-nitrogen bonds with organosilicon compounds are described. The reaction proceeds under mild conditions and exhibits a broad substrate scope with respect to both cyclic and acyclic alkylsilyl peroxides in combination with carbon and nitrogen sources. In particular, this approach enables the facile radical perfluoroalkylation using commercially available perfluoroalkyltrimethylsilanes. Our mechanistic studies suggest that the reaction should proceed via a free-radical process.

In-situ-generation of alkylsilyl peroxides from alkyl hydroperoxides and their subsequent copper-catalyzed functionalization with organosilicon compounds

Alkylsilyl peroxides were generated in situ from the corresponding alkyl hydroperoxides using organosilicon compounds of the type Me3SiX (X = CN, N3, and halogens) and an amine base. Subsequent in situ copper-catalyzed homolytic cleavage of the alkylsilyl peroxides afforded alkyl radicals, which were then trapped with X (X = CN, N3, and halogens) to furnish products with new carbon-carbon, carbon-nitrogen, or carbon-halogen bonds in good to high yields.

Syntheses of Pyrroles, Pyridines, and Ketonitriles via Catalytic Carbopalladation of Dinitriles

The first example of the Pd-catalyzed addition of organoboron reagents to dinitriles, as an efficient means of preparing 2,5-diarylpyrroles and 2,6-diarylpyridines, has been discussed here. Furthermore, the highly selective carbopalladation of dinitriles with organoboron reagents to give long-chain ketonitriles has been developed as well. Based on the broad scope of substrates, excellent functional group tolerance, and use of commercially available substrates, the Pd-catalyzed addition reaction of arylboronic acid and dinitriles is expected to be significant in future synthetic procedures.