38982-12-6

Basic information

• Product Name: 3-(9-Anthryl)acrylaldehyde
• Synonyms: 3-(9-anthryl)acrylaldehyde;3-(9-ANTHRYL)ACROLEIN;3-(9-ANTHRYL) ACROLEIN,99%MIN [GC];3-(Anthracen-9-yl)propenal;Anthracene-9-propenal;3-(9-Anthryl)acrylal;3-(9-Anthryl)propenal;3-(9-Anthryl)acrolein (Anthacrolein)
• CAS NO: 38982-12-6
• Molecular Formula: C₁₇H₁₂O
• Molecular Weight: 232.28
• EINECS: 254-235-0
• Product Categories: Anthracene series
• Mol File: 38982-12-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 173-175 °C
• Boiling Point: 458.316 °C at 760 mmHg
• Flash Point: 173.838 °C
• Appearance: /
• Density: 1.185 g/cm³
• Vapor Pressure: 1.39E-08mmHg at 25°C
• Refractive Index: 1.727
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Chloroform
• CAS DataBase Reference: 3-(9-Anthryl)acrylaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(9-Anthryl)acrylaldehyde(38982-12-6)
• EPA Substance Registry System: 3-(9-Anthryl)acrylaldehyde(38982-12-6)

Safety Data

• Hazardous Substances Data: 38982-12-6(Hazardous Substances Data)

Usage

General Description

3-(9-Anthryl)acrylaldehyde is a chemical compound with a molecular formula C21H14O. It is a fluorescent dye derivative with a naphthalene ring structure and an aldehyde functional group, used in various applications such as fluorescent imaging, chemical sensors, and organic light-emitting diodes. The compound is known for its unique photochemical and photophysical properties, making it a valuable tool in the field of materials science and biochemistry. The presence of the anthryl group allows for efficient energy transfer, making it useful in the development of optoelectronic devices and advanced chemical detection systems.

InChI:InChI=1/C17H12O/c18-11-5-10-17-15-8-3-1-6-13(15)12-14-7-2-4-9-16(14)17/h1-12H/b10-5+

Upstream product

• 3984-22-3 2-vinyl-1,3-dioxolane 
• 1564-64-3 9-Bromoanthracene 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 642-31-9 9-anthracene aldehyde 
• 2417-77-8 9-bromoethylanthracene 
• 107-02-8 acrolein 
• 172098-27-0 (E)-3-(anthracen-9-yl)prop-2-en-1-ol 

Downstream Products

• 1689-07-2 2-(anthracen-9-yl)thiophene 
• 615-15-6 2-Methyl-1H-benzimidazole 
• 81410-32-4 2-(anthracen-10-yl)-1H-benzo[d]imidazole 

Relevant articles and documents

Heck Reactions of Acrolein or Enones and Aryl Bromides – Synthesis of 3-Aryl Propenals or Propenones and Consecutive Application in Multicomponent Pyrazole Syntheses

3-(Hetero)aryl propenals or propenones are efficiently prepared by a Heck reaction of (hetero)aryl bromides and acrolein or vinyl ketones using Beller's CataCXium Ptb ligand under Jeffery's and Fu's conditions. The formation of these three-carbon building blocks is embedded into consecutive three- and pseudo-four-component syntheses of 3-(hetero)aryl and 3,5-diarylpyrazoles with a broad substitution pattern in moderate to excellent yield.

Heck arylation of acrolein acetals using the 9-bromoanthracene: A case of study

The influence of several parameters on the selectivity of the palladium catalysed Heck coupling of 9-bromoanthracene with acrolein acetals was studied. While the ester is the quasi exclusive product when only a base (i.e. NaOAc, K2CO3, etc.) is added in the medium, the presence of halide abstracting agent such as thallium or silver salts decreases noticeably the selectivity towards the ester. On the other hand, the addition of n-Bu4NOAc yields to the formation of the aldehyde with up to 74% selectivity. The presence of water was found to play a significant role not only on the rate but also on the selectivity of the reaction. A comprehensive mechanism is proposed outlining the influence of each additive, particularly on the selectivity of the reaction.

Wavelength dependent regioselective E→Z isomerization of 9-anthryldiene derivatives

9-Anthryldiene derivatives 1-5 are synthesized to study E→Z photoisomerization. Photoisomer composition upon direct excitation, and triplet-sensitized isomerization are determined. Quantum yield of isomerization, quantum yield of fluorescence and fluorescence life times are determined for these compounds. Interestingly, upon direct excitation the anthryldiene derivatives 1-3 carrying electron withdrawing end groups (EWG) displayed wavelength dependent regioselective E→Z isomerization from the singlet excited state. Triplet sensitization studies revealed that these anthryldiene derivatives undergo Z→E isomerization and not E→Z isomerization. The dual fluorescence observed for 1, 2, 3 and 2E, 4Z-1, indicates the involvement of two different emissive states. The fluorescence solvatochromism displayed by 1, 2, 3 and 2E, 4Z-1 is a clear indication of the involvement of a highly polarized/charge transfer singlet-excited state and the same is involved in the isomerization process. Fluorescence lifetimes measured for these compounds displayed bi-exponential behavior supporting the presence of two emissive states. A mechanism for photoisomerization is suggested.