4894-75-1

Basic information

• Product Name: 4-Phenylcyclohexanone
• Synonyms: TIMTEC-BB SBB008578;4-PHENYLCYCLOHEXANONE;4-PHENYLCYCLOHEXANONE, 98+%;Cyclohexanone, 4-phenyl-;4-Phenylcyclohexanone 98%;4-Phenyl-1-cyclohexanone;4-Phenylcyclohexane-1-one;4-Phenylcyclohexan-1-one 98%
• CAS NO: 4894-75-1
• Molecular Formula: C₁₂H₁₄O
• Molecular Weight: 174.24
• EINECS: 225-517-0
• Product Categories: Industrial/Fine Chemicals;Liquid Crystal intermediates;Miscellaneous;C11 to C12;Carbonyl Compounds;Ketones
• Mol File: 4894-75-1.mol
• Article Data: 110

Chemical Properties

• Melting Point: 73-77 °C(lit.)
• Boiling Point: 158-160°C 16mm
• Flash Point: 100°C
• Appearance: White to off-white/Crystalline Powder
• Density: 0.97 g/cm3 (25℃)
• Vapor Pressure: 0.00167mmHg at 25°C
• Refractive Index: 1.5363 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform, Methanol
• Water Solubility: slightly soluble
• BRN: 2045904
• CAS DataBase Reference: 4-Phenylcyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenylcyclohexanone(4894-75-1)
• EPA Substance Registry System: 4-Phenylcyclohexanone(4894-75-1)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 4894-75-1(Hazardous Substances Data)

Usage

Description

4-Phenylcyclohexanone is a white to off-white crystalline powder that is utilized in various chemical reactions and synthesis processes. It is a versatile compound with applications in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
4-Phenylcyclohexanone is used as a key intermediate in the synthesis of CCR2 antagonists, which are crucial for the treatment of various disease states such as rheumatoid arthritis and atherosclerosis. Its role in the synthesis process is to provide a structural framework that can be further modified to create the desired therapeutic agents.
Used in Chemical Industry:
4-Phenylcyclohexanone is used in the preparation of coumarins, which are important organic compounds with a wide range of applications, including pharmaceuticals, agrochemicals, and dyes. The synthesis involves dehydrogenation and Heck coupling reactions, showcasing the versatility of 4-Phenylcyclohexanone in various chemical transformations.
Used in Polymer Industry:
4-Phenylcyclohexanone was used in the preparation of a new cardo diamine monomer, 1,1-bis[4-(4-aminophenoxy)phenyl]-4-phenylcyclohexane bearing a 4-phenylcyclohexylidene unit. This monomer can be further utilized in the development of advanced polymer materials with specific properties and applications.
General Description:
4-Phenylcyclohexanone is known for its reactivity in various chemical reactions, such as the Ruthenium-catalyzed reaction with tributylamine, which yields 2-butyl-4-phenylcyclohexanone and 2,6-dibutyl-4-phenylcyclohexanone. Additionally, the Wittig reaction of 4-Phenylcyclohexanone with (carbethoxymethylene)triphenylphosphorane under microwave irradiation has been investigated, further demonstrating its potential in synthetic chemistry.

InChI:InChI=1/C12H14O/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-5,11H,6-9H2

Upstream product

• 930-68-7 cyclohexenone 
• 25163-93-3 8-phenyl-1,4-dioxaspiro[4,5]decane 
• 5437-46-7 trans-4-phenylcyclohexanol 
• 827-52-1 1-phenyl-1-cyclohexane 
• 752948-89-3 4-Phenyl-1-nitrocyclohexan 
• 5769-13-1 4-phenyl-cyclohexanol 
• 1444-93-5 4-phenyl-1,2-cyclohexanedicarboxylic acid 
• 108164-51-8 1,1-diethylthio-4-phenylcyclohexane 
• 128881-92-5 C₂₄H₂₄S₂ 
• 29916-50-5 C₁₂H₁₄NO₂^(1-) 
• 139021-96-8 9-phenyl-1,5-dithia-spiro[5.5]undecane 
• 81929-32-0 4-phenylcyclohexanone diethyl acetal 
• 92-69-3 4-Phenylphenol 
• 86724-17-6 4-methyl-N’-(4-phenylcyclohexylidene)benzenesulfono hydrazide 

Downstream Products

• 67688-28-2 4-phenylcycloheptanone 
• 1079-68-1 (+/-)-trans-2-bromo-4-phenyl-cyclohexanone 
• 109337-60-2 4-phenylcyclohexan-1-d-1-ol 
• 102162-15-2 1-(2-Methoxy-phenyl)-4-phenyl-cyclohexanol 
• 5977-10-6 Biligen 
• 27591-20-4 4-(4-phenyl-cyclohex-1-enyl)-morpholine 
• 33384-15-5 1-(2,2'-Dimethyl-4-biphenylyl)-4-phenylcyclohexen 
• 37416-23-2 2-(4-Phenyl-cyclohex-1-enyl)-propionic acid ethyl ester 
• 28125-94-2 1-(4-phenyl-cyclohex-1-enyl)-pyrrolidine 
• 2862-92-2 1-methyl-4-phenylcyclohexan-1-ol 
• 152387-04-7 (R)-(4-Phenylcyclohexen-1-enyloxy)trimethylsilane 
• 115880-04-1 ethyl 2-(4-phenylcyclohexylidene)acetate 
• 87996-26-7 1-tert-Butoxymethyl-4-phenyl-cyclohexanol 
• 122948-47-4 4-phenylcyclohex-1-enyl trifluoromethanesulfonate 

Relevant articles and documents

Merging Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Suzuki-Miyaura-Type Cross-Coupling of Alkyl Iodides and Organoborons

We report here a mechanistically distinct approach to achieve Suzuki-Miyaura-type cross-couplings between alkyl iodides and aryl organoborons. This process requires a copper catalyst but, in contrast with previous approaches based on palladium and nickel

Deciphering Reactivity and Selectivity Patterns in Aliphatic C-H Bond Oxygenation of Cyclopentane and Cyclohexane Derivatives

A kinetic, product, and computational study on the reactions of the cumyloxyl radical with monosubstituted cyclopentanes and cyclohexanes has been carried out. HAT rates, site-selectivities for C-H bond oxidation, and DFT computations provide quantitative information and theoretical models to explain the observed patterns. Cyclopentanes functionalize predominantly at C-1, and tertiary C-H bond activation barriers decrease on going from methyl- and tert-butylcyclopentane to phenylcyclopentane, in line with the computed C-H BDEs. With cyclohexanes, the relative importance of HAT from C-1 decreases on going from methyl- and phenylcyclohexane to ethyl-, isopropyl-, and tert-butylcyclohexane. Deactivation is also observed at C-2 with site-selectivity that progressively shifts to C-3 and C-4 with increasing substituent steric bulk. The site-selectivities observed in the corresponding oxidations promoted by ethyl(trifluoromethyl)dioxirane support this mechanistic picture. Comparison of these results with those obtained previously for C-H bond azidation and functionalizations promoted by the PINO radical of phenyl and tert-butylcyclohexane, together with new calculations, provides a mechanistic framework for understanding C-H bond functionalization of cycloalkanes. The nature of the HAT reagent, C-H bond strengths, and torsional effects are important determinants of site-selectivity, with the latter effects that play a major role in the reactions of oxygen-centered HAT reagents with monosubstituted cyclohexanes.

INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND METHODS OF THEIR USE

There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the disclosure.