493-72-1

Basic information

• Product Name: 5-PHENYLCYCLOHEXANE-1,3-DIONE
• Synonyms: ASISCHEM C66298;5-PHENYL-1,3-CYCLOHEXANEDIONE;5-PHENYLCYCLOHEXANE-1,3-DIONE;RARECHEM AR PA 0039;5-Phenyl-1,3-cyclohexanedione,96%;(S)-1-Phenylcarbamoylmethyl-pyrrolidine-2-carboxylicacid;5-Phenylcyclohexane-1,3-dione 98%;1,3-Dioxo-5-phenylcyclohexane
• CAS NO: 493-72-1
• Molecular Formula: C₁₂H₁₂O₂
• Molecular Weight: 188.22
• EINECS: -0
• Product Categories: Miscellaneous;C11 to C12;Carbonyl Compounds;Ketones
• Mol File: 493-72-1.mol
• Article Data: 18

Chemical Properties

• Melting Point: 188 °C(lit.)
• Boiling Point: 283.23°C (rough estimate)
• Flash Point: 133.8 °C
• Appearance: off-white to light yellow powder
• Density: 1.0750 (rough estimate)
• Vapor Pressure: 6.91E-05mmHg at 25°C
• Refractive Index: 1.6010 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.92±0.20(Predicted)
• BRN: 1103470
• CAS DataBase Reference: 5-PHENYLCYCLOHEXANE-1,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-PHENYLCYCLOHEXANE-1,3-DIONE(493-72-1)
• EPA Substance Registry System: 5-PHENYLCYCLOHEXANE-1,3-DIONE(493-72-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 493-72-1(Hazardous Substances Data)

Usage

Description

5-Phenyl-1,3-cyclohexanedione is a 1,3-diketone, which is an organic compound known for its versatile chemical properties and reactivity. It is characterized by the presence of two carbonyl groups (C=O) on adjacent carbon atoms within a cyclohexane ring, with a phenyl group attached to the fifth carbon. This unique structure allows it to participate in various chemical reactions and form a wide range of derivatives.

Uses

Used in Pharmaceutical Industry:
5-Phenyl-1,3-cyclohexanedione is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to undergo condensation reactions with N-arylmethylene-2-naphthylamines makes it a valuable building block for the development of hexahydrobenzo[a]phenanthridin-4-one derivatives, which have potential applications in the treatment of various diseases.
Used in Chemical Synthesis:
In the field of chemical synthesis, 5-Phenyl-1,3-cyclohexanedione is used as a starting material for the preparation of benzophenanthridine derivatives. These derivatives are known for their diverse applications, including their use as dyes, pigments, and in the development of new materials with unique properties.
Used in Iodonium Betaine Preparation:
5-Phenyl-1,3-cyclohexanedione is also utilized in the preparation of iodonium betaine, a compound that has potential applications in various chemical processes, including polymerization reactions and the synthesis of other organic compounds.
Used in 2H-Pyrans Synthesis:
Furthermore, 5-Phenyl-1,3-cyclohexanedione is employed in the synthesis of various 2H-pyrans through iodine-catalyzed reactions. These 2H-pyrans are important intermediates in the development of pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C12H12O2/c13-11-6-10(7-12(14)8-11)9-4-2-1-3-5-9/h1-5,8,10,13H,6-7H2/t10-/m1/s1

Upstream product

• 60-29-7 diethyl ether 
• 127053-50-3 ethyl 5-oxo-3-phenylhexanoate 
• 141-52-6 sodium ethanolate 
• 64-17-5 ethanol 
• 51367-64-7 3-chloro-5-phenylcyclohex-2-en-1-one 
• 68427-48-5 2-diazo-5-phenylcyclohexane-1,3-dione 
• 1896-62-4 (E)-benzalacetone 
• 105-53-3 diethyl malonate 
• 108-46-3 recorcinol 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 93994-08-2 2,4,6-Tris-methoxycarbonyl-5-phenyl-cyclohexan-dion-(1,3) 
• 154181-09-6 diethyl 2-phenyl-4,6-dioxocyclohexane-1,3-dicarboxylate 
• 857778-18-8 3-bromo-5-phenylcyclohex-2-en-1-one 
• 7664-93-9 sulfuric acid 

Downstream Products

• 55815-00-4 3-methoxy-5-phenylcyclohex-2-ene-1-one 
• 20117-71-9 methylene bis<2-(5-phenylcyclohexan-1,3-dione)> 
• 92251-17-7 5-ethoxy-1,6-dihydro-[1,1'-biphenyl]-3(2H)-one 
• 612-71-5 1,3,5-triphenylbenzene 
• 6049-47-4 5-oxo-3-phenylhexanoic acid 
• 75-25-2 Bromoform 
• 4165-96-2 3-phenylglutaric acid 
• 635-51-8 2-phenylsuccinic acid 
• 5703-52-6 3-phenylhexanoic acid 
• 49673-74-7 3-phenyl-1-cyclohexanol 
• 5060-08-2 5-phenyl-cyclohexane-1,3-diol 
• 51367-64-7 3-chloro-5-phenylcyclohex-2-en-1-one 
• 91963-96-1 2-oxo-4-phenyl-adipic acid 
• 857778-18-8 3-bromo-5-phenylcyclohex-2-en-1-one 

Relevant articles and documents

Inhibition of Autophagy by a Small Molecule through Covalent Modification of the LC3 Protein

The autophagic ubiquitin-like protein LC3 functions through interactions with LC3-interaction regions (LIRs) of other autophagy proteins, including autophagy receptors, which stands out as a promising protein–protein interaction (PPI) target for the intervention of autophagy. Post-translational modifications like acetylation of Lys49 on the LIR-interacting surface could disrupt the interaction, offering an opportunity to design covalent small molecules interfering with the interface. Through screening covalent compounds, we discovered a small molecule modulator of LC3A/B that covalently modifies LC3A/B protein at Lys49. Activity-based protein profiling (ABPP) based evaluations reveal that a derivative molecule DC-LC3in-D5 exhibits a potent covalent reactivity and selectivity to LC3A/B in HeLa cells. DC-LC3in-D5 compromises LC3B lipidation in vitro and in HeLa cells, leading to deficiency in the formation of autophagic structures and autophagic substrate degradation. DC-LC3in-D5 could serve as a powerful tool for autophagy research as well as for therapeutic interventions.

Dehydrogenative Formation of Resorcinol Derivatives Using Pd/C-Ethylene Catalytic System

The conversion of substituted 1,3-cyclohexanediones to the alkyl ethers of resorcinol using a Pd/C-ethylene system is reported. In these reactions, ethylene works as a hydrogen acceptor. The efficient synthesis of resveratrol was achieved using this protocol as a key step. In addition, the direct formation of substituted resorcinols was carried out by adding K2CO3 into the reaction media.

Synthesis of new 3-phenyl substituted dibenzo-1,4-diazepin-1-one derivatives

A new series of 3-phenyl substituted dibenzo-1,4-diazepin-1-one derivatives were synthesised by condensation of 5-phenylcyclohexane-1,3-dione, o-phenylenediamine and benzaldehydes. All the compounds were characterised by IR, MS, 1H NMR and elemental analysis. The crystal structure of 3-phenyl-11-(2-chlorophenyl)-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e] [1,4]diazepin-1-one was determined by X-ray single-crystal diffraction.