Dibenzylideneacetone
General
Systematic name	1,5-diphenylpenta-1,4-dien-3-one
Other names	bis(2-phenylethenyl)ketone, dibenzalacetone, styrol ketone, bis(2-phenylvinyl)ketone, dibenzylidineacetone, distyryl ketone IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ...
Molecular formula	C17H14O
SMILES	O=C(/C=C/c1ccccc1)/C=C/c2ccccc2
Molar mass	234.29 g/mol
Appearance	yellow solid
CAS number	[538-58-9]
Properties
Density and phase	? g/cm³, ?
Solubility in water	not soluble
Melting point	110 - 112°C (383 - 385 K)
Related compounds	Methyl vinyl ketone
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Dibenzylideneacetone or dibenzalacetone or 1,5-diphenylpenta-1,4-dien-3-one is an organic compound. A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per volume. ... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that Solid solubility be merged into this article or section. ... This article describes water from a scientific and technical perspective. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The general structure of an enone An enone is an unsaturated chemical compound or functional group consisting of a conjugated system of an alkene and a ketone. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Benzene An organic compound is any member of a large class of chemical compounds whose molecules contain carbon, with the exception of carbides, carbonates, carbon oxides and elementary carbon. ...

The compound can be prepared in the laboratory by an aldol condensation of benzaldehyde and acetone with sodium hydroxide in a water / ethanol medium with the exclusive formation of the trans, trans isomer (melting point 107-111 °C). An Aldol condensation is an organic reaction where an enolate ion reacts with a carbonyl compound to form a β-hydroxyaldehyde or β-hydroxyketone followed by dehydration to a conjugated enone. ... The chemical compound benzaldehyde (C6H5CHO) consists of a benzene ring with an aldehyde group attached to one carbon. ... In chemistry, acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. ... Sodium hydroxide (NaOH), also known as lye or caustic soda, is a caustic metallic base. ... In chemistry, geometric isomerism is a form of stereoisomerism and describes the orientation of functional groups at the ends of a bond around which no rotation is possible. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ...

This reaction is frequently encountered in organic chemistry education as a laboratory procedure. The conversion proceeds via the intermediacy of benzylideneacetone. Organic chemistry is a specific discipline within the subject of chemistry. ...

Dibenzylideneacetone is used as a sunscreen component and it is used as a ligand in organometallic chemistry for instance in tris(dibenzylideneacetone)dipalladium(0)) or (dba)₃Pd₂. Sunscreen (also known as sunblock, suncream, suntan lotion) is a lotion, spray or other topical product that helps protect the skin from the suns ultraviolet radiation, and which reduces sunburn and other skin damage, ultimately leading to a lower risk of skin cancer. ... In chemistry, a ligand is an atom, ion, or molecule (see also: functional group) that generally donates one or more of its electrons through a coordinate covalent bond to, or shares its electrons through a covalent bond with, one or more central atoms or ions (these ligands act as a... Organometallic chemistry is the study of chemical compounds containing bonds between carbon and a metal. ...

Prolonged exposure to sunlight converts the compound in a [2+2]cycloaddition to a mixture of four cyclobutane isomers.^[1]. A Cycloaddition is a pericyclic reaction in which the net result is loss of two pi bonds and gain of two sigma bonds. ... Cyclobutane, C4H8, with a molecular mass of 56. ...

External links

• Dibenzalacetone Organic Syntheses, Coll. Vol. 2, p.167 (1943); Vol. 12, p.22 (1932) Article
• Lab procedure I
• Lab procedure II
• Datasheet commercial supplier
• Link page to external chemical sources.

Organic Syntheses is a scientific journal that Since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ...

References