4500-20-3

Basic information

• Product Name: 4-Phenylcyclohexane-1-oneoxime
• Synonyms: 4-Phenylcyclohexane-1-oneoxime;4-Phenylcyclohexanone oxime;4-phenyl-1-cyclohexanone oxime;4-phenylcyclohexan-1-one oxime;N-(4-phenylcyclohexylidene)hydroxylamine
• CAS NO: 4500-20-3
• Molecular Formula: C₁₂H₁₅NO
• Molecular Weight: 189.26
• Mol File: 4500-20-3.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 339.8°Cat760mmHg
• 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: 4-Phenylcyclohexane-1-oneoxime(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenylcyclohexane-1-oneoxime(4500-20-3)
• EPA Substance Registry System: 4-Phenylcyclohexane-1-oneoxime(4500-20-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 4500-20-3(Hazardous Substances Data)

Usage

General Description

4-Phenylcyclohexane-1-oneoxime, also known as PCCO, is a chemical compound with the molecular formula C12H15NO. It is a white solid that is used in organic synthesis as a protecting group for aldehyde and ketone functional groups. PCCO is known for its ability to undergo a range of reactions including reduction, E1cB elimination, and enolization. It is commonly used as a reagent in the synthesis of various organic compounds and can also serve as a precursor for the preparation of other chemicals. PCCO is a valuable tool in the field of organic chemistry and is utilized in a variety of research and industrial applications.

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

Upstream product

• 4894-75-1 1-phenyl-4-cyclohexanone 
• 5769-13-1 4-phenyl-cyclohexanol 

Downstream Products

• 7500-39-2 5-phenylazepan-2-one 
• 143589-30-4 N-(4-Phenyl-cyclohexyl)-hydroxylamine 
• 172847-44-8 C₂₄H₂₄NOP 
• 21060-33-3 trans-1-Nitro-4-phenyl-cyclohexan 
• 21060-32-2 cis-1-Nitro-4-phenyl-cyclohexan 
• 5769-10-8 trans-4-phenylcyclohexan-1-amine 
• 5769-30-2 cis-Benzoylamino-4-phenyl-cyclohexan 
• 5769-30-2 N-(trans-4-phenyl-cyclohexyl)-benzamide 
• 4894-75-1 1-phenyl-4-cyclohexanone 
• 499137-81-4 4-methoxy-2-(4-phenylcyclohexanoneoxime)-benzonitrile 
• 476373-78-1 O-methyl 4-phenylcyclohexanone oxime 
• 920743-04-0 4-phenylcyclohexanone oxime ethyl carbonate 
• 115668-03-6 trans-N-(Diphenylphosphinyl)-4-phenylcyclohexylamine 
• 115668-04-7 cis-N-(Diphenylphosphinyl)-4-phenylcyclohexylamine 

Relevant articles and documents

Application of Transaminases in a Disperse System for the Bioamination of Hydrophobic Substrates

The challenging bioamination of hydrophobic substrates has been attained through the employment of a disperse system consisting of a combination of a low polarity solvent (e. g. isooctane or methyl-tert-butylether), a non-ionic surfactant and a minimal amount of water. In these conditions, amine transaminases (ATA) were shown to efficiently carry out the reductive amination of variously substituted cyclohexanones, providing good conversions often coupled with a superior stereoselectivity if compared with the corresponding chemical reductive amination. An array of synthetically useful 4-substituted aminocyclohexanes was consequentially synthesized through biocatalysis, analyzed and stereochemically characterized. (Figure presented.).

Direct Catalytic Desaturation of Lactams Enabled by Soft Enolization

A direct catalytic method is described for the α,β-desaturation of N-protected lactams to their conjugated unsaturated counterparts under mildly acidic conditions. The reaction is consistently operated at room temperature and tolerates a wide range of functional groups, showing reactivity complementary to that of prior desaturation methods. Lactams with various ring sizes and substituents at different positions all reacted smoothly. The synthetic utility of this method is demonstrated in a concise synthesis of Rolipram. In addition, linear amides also prove to be competent substrates, and the phthaloyl-protected product serves as a convenient precursor to access various conjugated carboxylic acid derivatives. Strong bases are avoided in this desaturation approach, and the key is to merge soft enolization with a Pd-catalyzed oxidation process.

Synthesis of oximes with NH2OH.HCl/DOWEX(R)50WX4 system

The oximation of a variety of carbonyl compounds was efficiently carried out with DOWEX(R)50WX4/NH2OH·HCl system. The reactions were performed in ethanol to give Z-aldoximation isomers of aldehydes and E-oximaton of acetophenone derivatives in a perfect selectively. The oximation of compounds with two carbonyl groups was carried out selectively on one carbonyl moiety. Also, the oximation of aldehydes over ketones has been accomplished successfully by this system.