19226-99-4

Basic information

• Product Name: 2,5-bis[4-(dimethylamino)benzylidene]cyclopentanone
• CAS NO: 19226-99-4
• Molecular Formula: C₂₃H₂₆N₂O
• Molecular Weight: 346.4653
• Mol File: 19226-99-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 561.7°C at 760 mmHg
• Flash Point: 248.5°C
• Density: 1.167g/cm³
• Vapor Pressure: 1.2E-12mmHg at 25°C
• Refractive Index: 1.687
• CAS DataBase Reference: 2,5-bis[4-(dimethylamino)benzylidene]cyclopentanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-bis[4-(dimethylamino)benzylidene]cyclopentanone(19226-99-4)
• EPA Substance Registry System: 2,5-bis[4-(dimethylamino)benzylidene]cyclopentanone(19226-99-4)

Safety Data

• Hazardous Substances Data: 19226-99-4(Hazardous Substances Data)

Usage

General Description

2,5-bis[4-(dimethylamino)benzylidene]cyclopentanone, also known as bis(dimethylamino)benzylidene cyclopentanone, is a chemical compound with a complex molecular structure. It is a symmetrical bis-chalcone derivative, typically used as a fluoroionophore for lithium ions. 2,5-bis[4-(dimethylamino)benzylidene]cyclopentanone is characterized by two dimethylamino groups attached to the benzylidene moiety, which is connected to the cyclopentanone ring. The unique structure of 2,5-bis[4-(dimethylamino)benzylidene]cyclopentanone gives it the ability to fluoresce in the presence of lithium ions, making it useful for lithium ion sensing applications. Additionally, it has potential applications in organic light-emitting diodes (OLEDs) and other optoelectronic devices due to its optoelectronic properties.

Upstream product

• 120-92-3 cyclopentanone 
• 100-10-7 4-dimethylamino-benzaldehyde 

Downstream Products

• 118816-10-7 2,5-Bis-[1-(4-dimethylamino-phenyl)-meth-(E)-ylidene]-cyclopentanol 

Relevant articles and documents

Structural and photophysical properties of alkylamino substituted 2-arylidene and 2,5-diarylidene cyclopentanone dyes

A series of alkylamino substituted 2-arylidene and 2,5-diarylidene cyclopentanone compounds were synthesized. Spectroscopic and photophysical properties of these compounds have been measured in a variety of solvents. Absorption and fluorescence maxima have been correlated with the Empirical Scale of Solvent Polarity (ET(30)). Theoretical TD-DFT spectral calculations and Lippert-Mataga analysis support the internal charge transfer (ICT) nature of the S0 → S1 excitation for these compounds, with higher degrees of ICT depicted for the alkylamino substituted 2,5-diarylidene cyclopentanones. Photophysical properties consisted of measuring the fluorescence quantum yields (Φf) and lifetimes (τf) in a variety of solvents. Radiative and nonradiative decay constants have been determined from the Φf and τf data. Variation with solvent in the nonradiative rate of decay is interpreted in terms of a competition between internal conversion and intersystem crossing. Lastly, two compounds presented have been shown to undergo excited state protonation in glacial acetic acid.

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.

Sulfuric acid-modified PEG-6000 (PEG-SO3H): An efficient, bio-degradable and reusable catalyst for synthesis of α, α′ bis(arylidene) cycloalkanones under solvent-free conditions

A green and efficient method for synthesis of α, α′ -bis (arylidene) cycloalkanones, starting from aromatic aldehydes in reaction with ketones using sulfonated polyethylene glycol 6000 (PEG-SO3H) as a stable, reusable and biodegradable catalyst under solvent-free conditions at 80 °C is described. The use of a nontoxic, inexpensive, easily available and recyclable catalyst makes this protocol practical, environmentally friendly and economically attractive.