3580-38-9

Basic information

• Product Name: 2-BENZOYLCYCLOHEXANONE
• Synonyms: 2-BENZOYLCYCLOHEXANONE;(R,S)-2-Benzoyl-cyclohexanone;2-(Benzoyl)cyclohexan-1-one;2-Benzoyl-1-cyclohexanone;2-Benzoylcyclohexanenone;2-phenylcarbonylcyclohexan-1-one;2-Benzoylcyclohexanone 98%
• CAS NO: 3580-38-9
• Molecular Formula: C₁₃H₁₄O₂
• Molecular Weight: 202.25
• Product Categories: Miscellaneous;C13 to C14;Carbonyl Compounds;Ketones
• Mol File: 3580-38-9.mol
• Article Data: 35

Chemical Properties

• Melting Point: 88-91 °C(lit.)
• Boiling Point: 343.7 °C at 760 mmHg
• Flash Point: 128.9 °C
• Appearance: /
• Density: 1.123 g/cm³
• Vapor Pressure: 6.89E-05mmHg at 25°C
• Refractive Index: 1.551
• Storage Temp.: 2-8°C
• PKA: 9.86±0.20(Predicted)
• CAS DataBase Reference: 2-BENZOYLCYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BENZOYLCYCLOHEXANONE(3580-38-9)
• EPA Substance Registry System: 2-BENZOYLCYCLOHEXANONE(3580-38-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 3580-38-9(Hazardous Substances Data)

Usage

Description

2-Benzoylcyclohexanone is an organic compound that can be synthesized through the reaction between silyl enol ether of cyclohexanone and benzoyl fluoride. It is a valuable intermediate in the synthesis of various pharmaceuticals and chemical products due to its unique chemical structure.

Uses

Used in Pharmaceutical Industry:
2-Benzoylcyclohexanone is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its ability to form different chemical bonds and reactions makes it a versatile building block in the development of new drugs.
Used in Chemical Industry:
In the chemical industry, 2-Benzoylcyclohexanone is utilized as a starting material for the production of various specialty chemicals, such as fragrances, dyes, and additives. Its unique structure allows for a wide range of applications in the creation of novel compounds with specific properties.
Used in Research and Development:
2-Benzoylcyclohexanone is also employed in research and development settings, where it is used to study the properties and reactivity of organic compounds. Its synthesis and subsequent reactions can provide valuable insights into the behavior of similar molecules, contributing to the advancement of organic chemistry.
Overall, 2-Benzoylcyclohexanone is a versatile and valuable compound with applications in various industries, including pharmaceuticals, chemicals, and research and development. Its unique structure and reactivity make it an essential component in the synthesis of a wide range of products and contribute to the ongoing development of new technologies and applications.

Synthesis Reference(s)

Tetrahedron Letters, 43, p. 2945, 2002 DOI: 10.1016/S0040-4039(02)00432-X

InChI:InChI=1/C13H14O2/c14-12-9-5-4-8-11(12)13(15)10-6-2-1-3-7-10/h1-3,6-7,11H,4-5,8-9H2

Upstream product

• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 98-88-4 benzoyl chloride 
• 93-58-3 benzoic acid methyl ester 
• 108-94-1 cyclohexanone 
• 41097-94-3 2-(1,2-diphenyl-vinyl)-cyclohexanone 
• 98815-41-9 2-(α-aminobenzylidene)-cyclohexanone 
• 670-80-4 4-cyclohexen-1-ylmorpholine 
• 3277-27-8 diethyl benzoylphosphonate 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 21300-30-1 lithium 1-cyclohexenolate 
• 96519-99-2 (Z)-2-((isopropylamino)(phenyl)methylene)cyclohexanone 
• 613-90-1 benzoyl cyanide 
• 107-98-2 1-methoxy-2-propanol 
• 96519-98-1 2-[1-tert-Butylamino-1-phenyl-meth-(Z)-ylidene]-cyclohexanone 

Downstream Products

• 105206-07-3 cis-α-<2-<(2-furanylmethyl)methylamino>cyclohexyl>benzenemethanol 
• 196810-09-0 (S)-2-<(2-benzoylphenyl)amino>-3-(4-hydroxyphenyl)propionic acid methyl ester 
• 278170-46-0 (R)-2-(2-Benzoyl-phenylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester 
• 7472-43-7 6-benzoylhexanoic acid 
• 128402-09-5 4-benzoyl-2-methylcyclohexanone 
• 278170-47-1 2-((2-benzoylphenyl)amino)-3-(4-hydroxyphenyl)-propionic acid methyl ester 
• 112665-41-5 ethyl 7-oxo-7-phenylheptanoate 
• 1234705-19-1 7-oxo-7-phenyl-heptanoic acid phenethyl ester 
• 94-47-3 2-Phenylethyl benzoate 

Relevant articles and documents

Generation and trapping of electron-deficient 1,2-cyclohexadienes. Unexpected hetero-Diels-Alder reactivity

Keto-substituted 1,2-cyclohexadienes were generated by base-mediated (KOt-Bu) elimination, and found to dimerize via an unprecedented formal hetero-Diels-Alder process, followed by hydration. These highly reactive cyclic allene intermediates were also tra

The involvement of l-arginine-nitric oxide-cgmp-atp-sensitive k+ channel pathway in antinociception of bbhc, a novel diarylpentanoid analogue, in mice model

The present study focuses on the possible involvement of L-arginine-nitric oxide-cGMP-ATP-sensitive K+ channel pathway in the antinociceptive activity of a novel diarylpentanoid analogue, 2-benzoyl-6-(3-bromo-4-hydroxybenzylidene)cyclohexen-1-ol (BBHC) via a chemical nociceptive model in mice. The antinociceptive action of BBHC (1 mg/kg, i.p.) was attenuated by the intraperi-toneal pre-treatment of L-arginine (a nitric oxide synthase precursor) and glibenclamide (an ATP-sensitive K+ channel blocker) in acetic acid-induced abdominal constriction tests. Interestingly, BBHC’s antinociception was significantly enhanced by the i.p. pre-treatment of 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one (ODQ), a selective inhibitor of soluble guanylyl cyclase (p + channel pathway, without any potential sedative or muscle relaxant concerns.

Design and synthesis of a novel mPGES-1 lead inhibitor guided by 3D-QSAR CoMFA

The search of novel mPGES-1 inhibitors has recently intensified probably due to the superior safety in comparison to existing anti-inflammatory drugs. Although two mPGES-1 inhibitors have entered clinical trials, none has yet reached the market. In this study, we performed modifications guided by 3D-QSAR CoMFA on 2, which is an unsymmetrical curcumin derivative with low binding affinity towards mPGES-1. To counter the PAINS properties predicted for 2, the diketone linker was replaced with a pyrazole ring. On the other hand, both prenyl and carboxylate ester groups were introduced to improve the activity. When tested in vitro, 11 suppressed PGE2 biosynthesis in activated macrophages and showed promising human mPGES-1 inhibition in microsomes of interleukin-1β-stimulated A549 cells. Altogether, 11 has been identified as a potential mPGES-1 inhibitor and could be a promising lead for a novel class of mPGES-1 inhibitors.