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

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 1,5-Diphenylpenta-1,4-dien-3-one
• Synonyms: (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one
• Molecular Formula: C₁₇H₁₄O
• Molecular Weight: 234.29
• CAS Registry Number: 538-58-9
• EC Number: 208-697-5
• SMILES: C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 113 ºC
• Index of Refraction: 1.650, Calc.^*
• Boiling Point: 400.7±34.0 ºC (760 mmHg), Calc.^*
• Flash Point: 176.1±20.6 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H315-H317-H319-H335-H400-H410
• Precautionary Statements: P261-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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1B	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332

Discovory and Applicatios

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.