22591-17-9

Basic information

• Product Name: 2-Phenylcyclohexanone oxime
• Synonyms: 2-Phenylcyclohexanone oxime
• CAS NO: 22591-17-9
• Molecular Formula: C₁₂H₁₅NO
• Molecular Weight: 189.25
• Mol File: 22591-17-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 339.8°C at 760 mmHg
• Flash Point: 210.7°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 3.48E-05mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: 2-Phenylcyclohexanone oxime(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenylcyclohexanone oxime(22591-17-9)
• EPA Substance Registry System: 2-Phenylcyclohexanone oxime(22591-17-9)

Safety Data

• Hazardous Substances Data: 22591-17-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H15NO/c14-13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-3,6-7,11,14H,4-5,8-9H2/b13-12-

Upstream product

• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 5470-11-1 hydroxylamine hydrochloride 
• 108-94-1 cyclohexanone 
• 108-86-1 bromobenzene 

Downstream Products

• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 111742-99-5 hexahydro-7-phenyl-1H-azepin-2-one 
• 28353-03-9 6-oxo-6-phenylhexanenitrile 
• 1217438-37-3 2-phenylcyclohexanone O-acetyl oxime 
• 115668-07-0 cis-N-(Diphenylphosphinyl)-2-phenylcyclohexylamine 
• 115668-07-0 trans-N-(Diphenylphosphinyl)-2-phenylcyclohexylamine 
• 165385-60-4 3,4,5,6-tetrahydro-7-methoxy-2-phenyl-2H-azepine 
• 17293-45-7 trans-2-phenylcyclohexylamine 
• 172847-54-0 C₂₄H₂₄NOP 

Relevant articles and documents

Visible-Light Photoredox-Catalyzed Dicarbofunctionalization of Styrenes with Oxime Esters and CO2: Multicomponent Reactions toward Cyanocarboxylic Acids and γ-Keto Acids

A photoredox-catalyzed dicarbofunctionalization of styrenes with oxime esters and CO2 has been achieved. Notably, a series of four-, five-, or six-membered cyclic ketone oximes worked well to furnish a wide range of ε-, ζ-, and η-cyanocarboxylic acids in good yields. Furthermore, a series of γ-keto acids also could be obtained by employing acyclic ketone oxime esters as the carbonyl radical precursor. It provides convergent access to diverse biologically important cyanocarboxylic and γ-keto acids.

Photoinduced C—C Bond Cleavage and Oxidation of Cycloketoxime Esters

A novel structural reorganization of cycloketoxime esters beyond the traditional Beckmann rearrangement process has been established to build cyano-containing ketones in the presence of photocatalyst. This novel transformation is remarkable with selective C—C bond cleavage and an oxidation process enabled by DMSO used as the solvent, oxidant, and oxygen source avoiding acid, base and toxic cyanide salts as the cyano source. Further applications in late-stage modification of complex and chiral molecules have also been reported.

Stereoselective hydride reductions of cyclic N-diphenylphosphinyl imines. Highly diastereoselective syntheses of protected primary amines

Reduction of N-diphenylphosphinyl imines of variously substituted cyclohexanones, cyclopentanones, and bicyclic ketones with lithium tri-sec-butylborohydride provides highly diastereoselective procedures for the syntheses of N-diphenylphosphinyl amines which represent protected primary amines that can be unmasked by mild acidic cleavage. Attack of cyclohexyl derivatives occurs almost exclusively via equatorial approach to yield axial amine derivatives while cyclopentyl and bicyclic imines are attacked from the less sterically encumbered faces.