What Is Benzalacetone?
Benzalacetone, also known as benzylideneacetone, is an organic compound with the structure C6H5CH=CHC(O)CH3. Its CAS registry number is 122-57-6, and it exists in both cis and trans structures, although typically only the trans form is observed.
Uses of Benzalacetone
Benzalacetone is commonly used in the fragrance industry, known for its sweet pea-like odor. It is particularly prominent in soap fragrances to mask the oily smell of natural oils and fats used in soap making.
Properties of Benzalacetone
Benzalacetone appears as a light yellow or yellow to yellowish-brown mass or liquid with a clear, characteristic odor. It has a melting point of 37-41°C, a boiling point of 262°C, and a flash point of 66°C. Its chemical formula is C10H10O, and it has a molecular weight of 146.19. As an α,β-unsaturated ketone, benzalacetone is slightly acidic at the α and β positions.
Other Information on Benzalacetone
1. Synthesis of Benzalacetone
Benzalacetone can be synthesized from acetone and benzaldehyde through a NaOH-induced condensation reaction.
2. Reaction of Benzalacetone
Benzalacetone’s enolate can react in various ways, including bromine addition to the double bond and formation of hydrazone. It can also participate in Diels-Alder reactions to synthesize dihydropyran.
3. Applications of Benzalacetone
When reacted with diiron nonacarbonyl, benzalacetone forms (benzylideneacetone)iron tricarbonyl, transferring Fe(CO)3 units to other organic compounds.
4. Related Compounds of Benzalacetone
Using benzalacetone’s enolate, dibenzalacetone can be synthesized by condensing benzaldehyde to the methyl group. Dibenzalacetone, also known as dibenzylideneacetone, serves as a transition metal ligand and is abbreviated as dba.