Benzylacetone
[CAS# 2550-26-7]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Ketone fragrance >> Aromatic ketone fragrance
• Name: Benzylacetone
• Synonyms: 4-Phenyl-2-butanone; 4-Phenylbutan-2-one
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.20
• CAS Registry Number: 2550-26-7
• EC Number: 219-847-4
• SMILES: CC(=O)CCC1=CC=CC=C1

Properties

• Water solubility: PRACTICALLY INSOLUBLE
• Density: 1.0±0.1 g/mL, Calc.^*, 0.988 g/mL (Expl.)
• Index of Refraction: 1.504, Calc.^*, 1.512 (Expl.)
• Boiling Point: 233.5 ºC (760 mmHg), Calc.^*, 235 ºC (Expl.)
• Flash Point: 98.3 ºC, Calc.^*, 105 ºC (Expl.)

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319
• Precautionary Statements: P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

Benzylacetone, also known as 1-phenyl-2-propanone, is an organic compound with the molecular formula C9H10O. It is a colorless to pale yellow liquid with a characteristic pleasant, sweet, floral odor. Benzylacetone was first synthesized in the early 20th century and has since been used in a variety of applications, particularly in the fragrance and flavor industries.

The compound is commonly produced through the benzylation of acetone, using benzyl chloride in the presence of a base such as sodium hydroxide. It can also be synthesized via the Friedel-Crafts acylation of toluene with acetic acid in the presence of a Lewis acid catalyst.

Benzylacetone finds extensive use as a fragrance and flavor ingredient. It has a sweet, honey-like aroma with floral and almond-like notes, which makes it a popular additive in perfumes, soaps, and cosmetics. In the food industry, it is used as a flavoring agent, particularly in baked goods, candies, and beverages, where it imparts a mild, sweet, and slightly nutty flavor.

Apart from its application in the fragrance and flavor industries, benzylacetone is also used as an intermediate in organic synthesis. It serves as a building block in the production of various chemicals, including pharmaceuticals and agrochemicals. It is involved in the synthesis of more complex compounds such as the synthesis of β-phenylethylamine and other aromatic derivatives.

Benzylacetone is generally regarded as safe for use in fragrance and flavor applications, with low toxicity reported in the available literature. However, like many organic chemicals, it should be handled with care to avoid prolonged exposure to high concentrations, which could potentially cause irritation or other adverse effects.

In summary, benzylacetone is a versatile and valuable compound widely used in the fragrance, flavor, and chemical industries. Its pleasant aroma and flavor characteristics have made it an important component in many consumer products. Additionally, its role as a precursor in organic synthesis highlights its broader applications in chemical manufacturing.

References

2024. A review on natural phenylbutanoid attractants: Occurrence, distribution, and role in nature, especially in relation to Dacini fruit fly behavior and pollination. Journal of Chemical Ecology, 50(3-4).
DOI: 10.1007/s10886-024-01499-6

2023. Discovery of Insect Attractants Based on the Functional Analyses of Female-Biased Odorant Receptors and Their Orthologs in Two Closely Related Species. Journal of Agricultural and Food Chemistry, 71(47).
DOI: 10.1021/acs.jafc.3c05368

2023. Practical N-alkylation via homogeneous iridium-catalyzed direct reductive amination. Science China Chemistry, 66(3).
DOI: 10.1007/s11426-022-1494-7