Valerophenone
[CAS# 1009-14-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic ketone
• Name: Valerophenone
• Synonyms: 1-Phenyl-1-pentanone
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.23
• CAS Registry Number: 1009-14-9
• EC Number: 213-767-3
• SMILES: CCCCC(=O)C1=CC=CC=C1

Properties

• Density: 0.98
• Melting point: -9 °C
• Boiling point: 105-107 °C (5 mmHg)
• Refractive index: 1.5143-1.5163
• Flash point: 102 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

Valerophenone, also known as 1-phenyl-1-pentanone, is a ketone with the molecular formula C11H14O. It was first synthesized in the early 20th century during studies on aromatic ketones. The chemical structure of valerophenone, featuring a phenyl ring attached to a pentanone chain, made it an interesting subject for researchers exploring the properties and reactivity of ketones. Its relatively straightforward synthesis involves the Friedel-Crafts acylation of benzene with valeryl chloride, catalyzed by aluminum chloride. This discovery added to the understanding of ketone chemistry and paved the way for various applications in scientific and industrial fields.

Valerophenone is widely used as a photoinitiator in polymer chemistry. Photoinitiators are compounds that produce reactive species when exposed to light, initiating polymerization processes. In the case of valerophenone, its ability to absorb ultraviolet (UV) light and generate free radicals makes it effective in initiating the polymerization of monomers. This property is crucial in the production of various polymers and coatings, particularly in UV-curable inks, adhesives, and protective coatings.

Valerophenone serves as an important intermediate in organic synthesis. Its ketone functional group is highly reactive, allowing it to participate in various chemical reactions such as reductions, condensations, and Grignard reactions. This versatility makes it valuable for synthesizing a wide range of organic compounds, including pharmaceuticals, agrochemicals, and fragrances.

In the fragrance and flavor industry, valerophenone is used as an ingredient to impart specific scents and flavors. Its aromatic properties contribute to the creation of complex fragrance profiles in perfumes and scented products. Additionally, valerophenone and its derivatives are used to develop flavoring agents that enhance the taste of various food and beverage products.

Valerophenone is employed in research and development as a model compound to study the behavior of ketones and aromatic compounds. Its well-defined structure and reactivity make it an ideal subject for investigating reaction mechanisms, kinetics, and photochemical processes.

In materials science, valerophenone is used as a photocrosslinking agent. Photocrosslinking involves the formation of covalent bonds between polymer chains upon exposure to light, resulting in a network structure. This process enhances the mechanical properties and stability of polymeric materials. Valerophenone's ability to generate free radicals under UV light makes it suitable for this application, enabling the production of robust and durable materials used in coatings, adhesives, and other high-performance applications.

References

2021. Cu(I) mediated hydrogen borrowing strategy for the α-alkylation of aryl ketones with aryl alcohols. Monatshefte fur Chemie - Chemical Monthly, 152(3).
DOI: 10.1007/s00706-021-02735-5

2023. Solubilities and metal extraction behaviors for calix[4]arene acetic-acid derivatives in various organic solvents. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 103(1-2).
DOI: 10.1007/s10847-023-01178-1

1985. 2.8 Pharmazeutische Produkte. Fresenius Zeitschrift fur analytische Chemie, 320(7).
DOI: 10.1007/bf00487100