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

• 5437-46-7 trans-4-phenylcyclohexanol 
• 122948-47-4 4-phenylcyclohex-1-enyl trifluoromethanesulfonate 
• 27070-24-2 (3-bromo-1-(2-bromoethyl)-propyl)benzene 
• 250293-45-9 4-Phenylcyclohexanone N-phenylhydrazone 
• 5769-13-1 4-phenyl-cyclohexanol 
• 1064664-58-9 9-phenyl-1,5-dithiaspiro[5,5]undecane-1-oxide 
• 108-86-1 bromobenzene 
• 22460-52-2 4-bromocyclohexan-1-one 
• 87143-17-7 4-phenyl-1-methylenecyclohexane 
• 13482-22-9 4-hydroxycyclohexanone 
• 29916-50-5 C₁₂H₁₄NO₂^(1-) 
• 128881-92-5 C₂₄H₂₄S₂ 
• 108164-51-8 1,1-diethylthio-4-phenylcyclohexane 
• 1444-93-5 4-phenyl-1,2-cyclohexanedicarboxylic acid 

Downstream Products

• 102162-15-2 1-(2-Methoxy-phenyl)-4-phenyl-cyclohexanol 
• 141621-91-2 2,6-bis[(4-methylphenyl)methinyl]-4-phenylcyclohexanone 
• 141621-89-8 (2E,6E)-2,6-dibenzylidene-4-phenylcyclohexanone 
• 158745-64-3 8-Phenyl-1-thia-4-aza-spiro[4.5]decane-3-carboxylic acid ethyl ester 
• 115880-04-1 ethyl 2-(4-phenylcyclohexylidene)acetate 
• 204014-40-4 2-(4-phenylcyclohexylidene)acetic acid 
• 122948-47-4 4-phenylcyclohex-1-enyl trifluoromethanesulfonate 
• 106592-05-6 8-phenyl-1,4-dithia-spiro[4.5]decane 
• 91495-75-9 trans-3-phenylcyclopentanecarboxylic acid 

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

Ground-State Electron Transfer as an Initiation Mechanism for Biocatalytic C-C Bond Forming Reactions

The development of non-natural reaction mechanisms is an attractive strategy for expanding the synthetic capabilities of substrate promiscuous enzymes. Here, we report an "ene"-reductase catalyzed asymmetric hydroalkylation of olefins using α-bromoketones as radical precursors. Radical initiation occurs via ground-state electron transfer from the flavin cofactor located within the enzyme active site, an underrepresented mechanism in flavin biocatalysis. Four rounds of site saturation mutagenesis were used to access a variant of the "ene"-reductase nicotinamide-dependent cyclohexanone reductase (NCR) from Zymomonas mobiles capable of catalyzing a cyclization to furnish β-chiral cyclopentanones with high levels of enantioselectivity. Additionally, wild-type NCR can catalyze intermolecular couplings with precise stereochemical control over the radical termination step. This report highlights the utility for ground-state electron transfers to enable non-natural biocatalytic C-C bond forming reactions.

Zinc substituted Keggin-type polyoxometalate on Dowex: a green heterogeneous catalyst for oxidation of alcohols in water

In this work, homogeneous and heterogeneous oxidation of alcohols by H2O2 in the presence of [(n-C4H9)4?N]5[PW11ZnO39].3H2O and [PW11ZnO39]5? supported on Dowex 22 as catalysts have been investigated. Using water as a green solvent, different alcohols were converted into the corresponding aldehydes and ketones in high to excellent yields. Dowex 22 supported polyoxometalate, PW11Zn@Dowex, was also catalyzed highly robust and selective oxidation of unsaturated alcohols. Leaching and recycling experiments on supported catalyst revealed the excellent stability and reusability of this catalytic system.