34200-53-8

Basic information

• Product Name: 2-[[4-(diethylamino)phenyl]methylene]-1H-indene-1,3(2H)-dione
• Synonyms: 2-[[4-(diethylamino)phenyl]methylene]-1H-indene-1,3(2H)-dione;2-[4-(Diethylamino)benzylidene]-1,3-indandione;2-[4-(Diethylamino)benzylidene]-2H-indene-1,3-dione;2-[4-(diethylamino)benzylidene]-1H-indene-1,3(2H)-dione
• CAS NO: 34200-53-8
• Molecular Formula: C₂₀H₁₉NO₂
• Molecular Weight: 305.37036
• EINECS: 251-874-7
• Mol File: 34200-53-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 509.2°Cat760mmHg
• Flash Point: 231.8°C
• Appearance: /
• Density: 1.219g/cm³
• Vapor Pressure: 1.73E-10mmHg at 25°C
• Refractive Index: 1.664
• CAS DataBase Reference: 2-[[4-(diethylamino)phenyl]methylene]-1H-indene-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[[4-(diethylamino)phenyl]methylene]-1H-indene-1,3(2H)-dione(34200-53-8)
• EPA Substance Registry System: 2-[[4-(diethylamino)phenyl]methylene]-1H-indene-1,3(2H)-dione(34200-53-8)

Safety Data

• Hazardous Substances Data: 34200-53-8(Hazardous Substances Data)

Usage

Physical state

Yellow to orange solid

Uses

Solvent dye in textile, plastics, and printing industries

Fluorescence properties

Useful in research and analytical applications

Therapeutic potential

Anti-inflammatory and anti-cancer activities

Chemical structure

Derivative of indene-1,3(2H)-dione with a diethylamino substituent on the phenyl ring.

InChI:InChI=1/C20H19NO2/c1-3-21(4-2)15-11-9-14(10-12-15)13-18-19(22)16-7-5-6-8-17(16)20(18)23/h5-13H,3-4H2,1-2H3

Upstream product

• 606-23-5 1H-indene-1,3(2H)-dione 
• 40046-95-5 N,N-diethyl-4-((phenylimino)methyl)aniline 
• 120-21-8 4-Diethylaminobenzaldehyde 

Relevant articles and documents

2-(p-diethylaminobenzylidene)-1,3-indandione

The title compound, C20H19NO2, belongs to the class of donor-acceptor-substituted conjugated polyenes. Within the structure, O atoms are situated in the plane of the 1,3-indandione fragment and the N atom lies in the plane of the p-benzylidene fragment which forms a dihedral angle of 7.6 (2)° with the indandione nucleus.

Synthesis, electronic, and electro-optical properties of emissive solvatochromic phenothiazinyl merocyanine dyes

Phenothiazinyl merocyanine dyes with variable substitution patterns on the peripheral benzene ring were synthesized in good yields by Knoevenagel condensation of the corresponding phenothiazinyl aldehydes and N-methylrhodanine or indan-1,3-dione. The electronic properties were investigated by cyclic voltammetry, absorption, electro-optical absorption, and emission spectroscopy. All these merocyanines reveal reversible redox behavior that stems from the phenothiazinyl-centered oxidation to give stable radical cations. The redox potentials strongly correlate with Hammett σp parameters. All merocyanines reveal large Stokes shifts. They also display a pronounced emissive solvatochromism, which is caused by large dipole moment changes upon excitation from the ground to the excited state. These findings are supported by solvatochromism studies and time-dependent DFT computations. A dye-ing breed: Phenothiazinyl-merocyanine dyes with variable substitution patterns on the peripheral benzene ring were synthesized in good yields by Knoevenagel condensation of the corresponding phenothiazinyl aldehydes and N-methylrhodanine or indan-1,3-dione. Their electronic properties were investigated by various methods (see figure). Copyright