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1,5-Diphenylpenta-1,4-dien-3-one
[CAS# 538-58-9]

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Identification
ClassificationOrganic raw materials >> Ketone compound
Name1,5-Diphenylpenta-1,4-dien-3-one
Synonyms(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one
Molecular StructureCAS # 538-58-9, 1,5-Diphenylpenta-1,4-dien-3-one
Molecular FormulaC17H14O
Molecular Weight234.29
CAS Registry Number538-58-9
EC Number208-697-5
SMILESC1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2
Properties
Density1.1±0.1 g/cm3, Calc.*
Melting point113 °C
Index of Refraction1.650, Calc.*
Boiling Point400.7±34.0 °C (760 mmHg), Calc.*
Flash Point176.1±20.6 °C, Calc.*
*Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbolssymbol symbol   GHS07;GHS09 Warning  Details
Risk StatementsH315-H317-H319-H335-H400-H410  Details
Safety StatementsP261-P264-P264+P265-P271-P272-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Skin sensitizationSkin Sens.1BH317
Chronic hazardous to the aquatic environmentAquatic Chronic1H410
Acute hazardous to the aquatic environmentAquatic Acute1H400
Skin irritationSkin Irrit.2H315
Eye irritationEye Irrit.2H319
Specific target organ toxicity - single exposureSTOT SE3H335
Acute toxicityAcute Tox.4H312
Acute toxicityAcute Tox.4H332
SDSAvailable
up Discovery and Applications
1,5-Diphenylpenta-1,4-dien-3-one is an important organic compound known for its distinctive structural features and versatile applications in various fields, particularly in organic synthesis and materials science. This compound belongs to the class of chalcones, which are characterized by a conjugated double bond system that contributes to their unique chemical properties. The synthesis of 1,5-diphenylpenta-1,4-dien-3-one typically involves the Claisen-Schmidt condensation reaction, where acetophenone and benzaldehyde are reacted in the presence of a base, leading to the formation of the desired product.

The discovery of 1,5-diphenylpenta-1,4-dien-3-one can be traced back to the exploration of chalcone derivatives in the mid-20th century. Researchers have focused on these compounds due to their interesting biological activities and their potential as building blocks for more complex molecular architectures. The extended π-conjugation in 1,5-diphenylpenta-1,4-dien-3-one not only enhances its stability but also imparts interesting optical properties, making it a candidate for various applications.

One of the significant applications of 1,5-diphenylpenta-1,4-dien-3-one lies in its role as a precursor in the synthesis of biologically active compounds. The compound has been studied for its potential antimicrobial, anti-inflammatory, and anticancer activities. Researchers have explored the modification of its structure to develop new derivatives that exhibit enhanced pharmacological properties. The ability to introduce various functional groups into the 1,5-diphenylpenta-1,4-dien-3-one framework allows chemists to tailor the compound for specific therapeutic applications, making it a valuable target in drug discovery programs.

In addition to its pharmaceutical relevance, 1,5-diphenylpenta-1,4-dien-3-one has also found applications in materials science. The compound can serve as a building block for the synthesis of polymers and materials with tailored properties. The incorporation of 1,5-diphenylpenta-1,4-dien-3-one into polymeric systems can enhance thermal stability and mechanical properties, making these materials suitable for various industrial applications, including coatings, adhesives, and electronic devices.

Moreover, the compound's ability to absorb light in the ultraviolet and visible regions has garnered interest in the field of photonics. Its incorporation into optical materials can lead to the development of sensors and other devices that utilize light for their operation. The photochemical behavior of 1,5-diphenylpenta-1,4-dien-3-one has been investigated for applications in organic light-emitting diodes (OLEDs) and other optoelectronic devices.

The ongoing research surrounding 1,5-diphenylpenta-1,4-dien-3-one continues to reveal new potential applications and derivatives. Its unique properties and versatility make it a compound of interest for scientists in various fields, ranging from medicinal chemistry to materials science. As new synthetic methods and modifications are developed, the future of 1,5-diphenylpenta-1,4-dien-3-one may unveil even more applications and insights into its behavior in different chemical contexts.

References

2019. Synthesis, characterization, molecular docking evaluation, antidepressant, and anti-Alzheimer effects of dibenzylidene ketone derivatives. Drug Development Research, 80(6).
DOI: 10.1002/ddr.21537

2018. Diastereoselective synthesis of cyclohexadienes via tandem cyclization strategies. Molecular Diversity, 22(4).
DOI: 10.1007/s11030-018-9900-x
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