895-80-7

Basic information

• Product Name: 2,5-DIBENZYLIDENECYCLOPENTANONE
• Synonyms: Cyclopentanone, 2,5-bis(phenylmethylene)- (9ci);Cyclopentanone, 2,5-dibenzylidene- (8ci);Nsc 71885;2,5-DIBENZYLIDENECYCLOPENTANONE;2,5-Bis(benzylidene)cyclopentane-1-one
• CAS NO: 895-80-7
• Molecular Formula: C₁₉H₁₆O
• Molecular Weight: 260.33
• Mol File: 895-80-7.mol
• Article Data: 44

Chemical Properties

• Melting Point: 192 °C
• Boiling Point: 462.9°C at 760 mmHg
• Flash Point: 205.7°C
• Appearance: /
• Density: 1.179g/cm³
• Vapor Pressure: 9.53E-09mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: 2,5-DIBENZYLIDENECYCLOPENTANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIBENZYLIDENECYCLOPENTANONE(895-80-7)
• EPA Substance Registry System: 2,5-DIBENZYLIDENECYCLOPENTANONE(895-80-7)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 895-80-7(Hazardous Substances Data)

Usage

General Description

2,5-Dibenzylidene-cyclopentanone is a chemical compound with the molecular formula C19H16O. It is commonly used as a reactant in organic synthesis, particularly in the production of various types of perfumes and fragrances. 2,5-DIBENZYLIDENECYCLOPENTANONE is known for its distinctive odor and is often used as a starting material for the synthesis of structurally complex molecules. Its unique structure and reactivity make it a valuable tool for organic chemists and researchers in the development of new and innovative chemical processes. Additionally, it has demonstrated potential biological activities, such as anti-tumor and anti-inflammatory properties, making it a subject of interest for pharmaceutical research.

InChI:InChI=1/C19H16O/c20-19-17(13-15-7-3-1-4-8-15)11-12-18(19)14-16-9-5-2-6-10-16/h1-10,13-14H,11-12H2/b17-13-,18-14+

Upstream product

• 917-64-6 methyl magnesium iodide 
• 96-41-3 Cyclopentanol 
• 100-52-7 benzaldehyde 
• 1921-90-0 2-benzylidenecyclopentanone 
• 141-52-6 sodium ethanolate 
• 120-92-3 cyclopentanone 
• 140653-89-0 (E)-benzylideneglyoxylic acid potassium salt 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 412323-29-6 3-benzo[1,3]dioxol-5-yl-3-(2-oxo-cyclopentyl)-1-phenyl-propan-1-one 
• 53778-21-5 2,5-dibromocyclopentan-1-one 
• 95127-15-4 methyl 3-(hydroxy(phenyl)methyl)-2-oxocyclopentanecarboxylate 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 57-13-6 urea 

Downstream Products

• 52186-05-7 cis/trans-2,5-dibenzylcyclopentanone 
• 872292-25-6 2,5-dibromo-2,5-bis-(α-bromo-benzyl)-cyclopentanone 
• 52186-15-9 2,5-dibenzylcyclopentanol 
• 6603-83-4 2,5-dibenzylidenecyclopentanol 
• 108223-13-8 7-benzylidene-4-phenyl-3-cyano-2-thioxo-2,5,6,7-tetrahydro-1H-pyrindines 
• 109970-97-0 1-phenyl-2-benzoylcyclopropane-3-spiro-3-(1-benzylidenecyclopentan-2-one) 
• 93651-35-5 2-benzylidene-5-cyclopentylidenecyclopentanone 
• 108158-58-3 phenylbis(3-benzylidene-2-oxocyclopentyl)methane 
• 73526-94-0 C₃₈H₃₂O₂ 
• 71803-91-3 2-(Dimethylphosphono)-benzyl-5-benzal-cyclopentanon 
• 6603-83-4 dibenzylidene-2,5 cyclopentanol 
• 134920-36-8 3a-hydroxy-8-phenyl-2'-oxo-3'-cyclopentylidenespiro<(1,2,3,3a,4,5,6,7,8,8a-sym-decahydroindacene)-4,1'-cyclopentane> 
• 134920-35-7 3,6-diphenyl-4,5a-ethano-7,8-cyclopent-1'⁽⁸⁾eno-2a,3,4,5,5a,6,7-heptahydroacenaphthen-5-one 
• 77821-81-9 7-Benzylidene-3-cyano-2-oxo-4-phenyl-2,5,6,7-tetrahydro-1H-1-pyrindine 

Relevant articles and documents

Green, rapid, and highly efficient syntheses of α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones as potentially biologic compounds via solvent-free microwave-assisted Claisen–Schmidt condensation catalyzed by MoCl5

A new, green, and highly efficient protocol for the expeditious preparation of some α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones via a simple microwave-assisted Claisen–Schmidt condensation reaction catalyzed by MoCl5 was successfully developed. Outstanding features of the current methodology include the use of solvent-free conditions, simple operation, use of a very inexpensive and available catalyst, low catalyst loading, short reaction times, high yields of the pure products, no harmful by-products, easy workup, and also the applicability of microwave irradiation as a clean source of energy. Furthermore, a gram-scale reaction was successfully conducted, proving the scalability of this current Claisen–Schmidt condensation reaction.

Diarylidenecyclopentanone derivatives as potent anti-inflammatory and anticancer agents

Cancer is often associated with chronic inflammation. In order to develop potential anticancer and anti-inflammatory agents a series of 26 diarylidenecyclopentanones (DACPs) Ia–Iv, II, III, and IV were synthesized. Five of the synthesized DACPs are novel (Ih, Ij, Ik, Is, and Iv), derivative Iv was characterized using single-crystal X-ray diffraction study. All the synthesized derivatives were tested for their anti-inflammatory as well as cytotoxicity properties. Compound Is is found to have the highest anti-inflammatory activity (93.67%) by inhibiting PGE2 (prostaglandin E2) production. Three of the DACPs (Io, It, and Iu) were observed to have high cytotoxicity with IC50 value of 8.73 ± 0.06 μM (Io), 12.55 ± 0.31 μM (It), and 11.47 ± 0.15 μM (Iu) against HeLa cells. Further staining and cell cycle analysis was done using these three DACPs to understand their mechanism of action. The G0/G1 phase was observed to be the longest one through which the cells undergo apoptosis.

Sulfonated PEG-intercalated montmorillonite [(Mt/PEG)-SO3H] as efficient and ecofriendly nanocatalyst for synthesis of α,α′-bis(substituted benzylidene)cycloalkanones

(Montmorillonite/PEG)-SO3H nanocomposite was successfully prepared for the first time and introduced as a solid acid nanocatalyst. Initially, polyethylene glycol (PEG) polymeric chains were intercalated into interlayer spaces of montmorillonite. The resulting Mt/PEG nanocomposite with good mechanical and thermal stability was chosen as a useful clay mineral/polymer support for further modification with chlorosulfonic acid. Structural characterization of (Mt/PEG)-SO3H was carried out using X-ray diffraction (XRD) analysis, Brunauer–Emmett–Teller (BET) measurements, Barrett–Joyner–Halenda (BJH) analysis, scanning electron microscopy (SEM), thermogravimetric analysis (TGA), and Fourier-transform infrared (FT-IR) spectroscopy. The results showed that PEG chains were intercalated into the clay mineral layers and that the Mt/PEG nanocomposite was successfully sulfonated. (Mt/PEG)-SO3H nanocomposite exhibited high specific surface area and good stability up to around 150?°C, showing excellent potential for application as a recyclable nanocatalyst. (Mt/PEG)-SO3H was used as an efficient and ecofriendly solid acid nanocatalyst for preparation of α,α′-bis(substituted benzylidene)cycloalkanones under solvent-free conditions, leading to many interesting findings. The excellent conversion values confirm that the catalyst has strong and sufficient acidic sites, which are responsible for its catalytic performance. The reaction under mild conditions (room temperature) with excellent yield, catalyst recyclability (up to ten times), and simple work-up procedure represent useful advantages of (Mt/PEG)-SO3H for catalysis. Moreover, the reaction could be scaled up to 10 and 15?mmol scales.