Benzylideneacetone
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| Benzylideneacetone | |
|---|---|
 |
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| General | |
| Systematic name | 4-Phenyl-3-buten-2-one |
| Other names | Benzalacetone Benzylideneacetone Methyl styryl ketone Benzylidene acetone |
| Molecular formula | C10H10O |
| SMILES | ? |
| Molar mass | 146.19 g/mol |
| Appearance | pale yellow solid |
| CAS number | [122-57-6] |
| Properties | |
| Density and phase | 1.008 g/cm3 |
| Solubility in water | 1.3 g/L |
| Other solvents | nonpolar solvents |
| Melting point | 39-42 °C |
| Boiling point | 260-262 °C |
| Structure | |
| Crystal structure | |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | irritant |
| NFPA 704 | |
| Flash point | 116 °C |
| R/S statement | R: 36/37/38-43 S: 22-26-36/37 |
| RTECS number | EN0330000 |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related compounds | Dibenzylideneacetone cinnamaldehyde |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Benzylideneacetone is the organic compound described by the formula C6H5CH=CHC(O)CH3. Although both cis and trans isomers are possible for the α,β-unsaturated ketone, only the trans isomer is observed. Its original preparation demonstrated the scope of condensation reactions to construct new, complex organic compounds.[1]
Contents |
[edit] Preparation
Benzylideneacetone can be efficiently prepared by the NaOH-induced condensation of the readily available reagents acetone and benzaldehyde:[2]
- CH3C(O)CH3 + C6H5CHO → C6H5CH=CHC(O)CH3 + H2O
[edit] Reactions
The compound undergoes the reactions expected for its collection of functional groups: e.g., the double bond adds bromine, the heterodiene adds electron-rich alkenes in Diels-Alder reactions to give dihydropyrans, the methyl group undergoes further condensation with benzaldehyde to give dibenzylideneacetone, and the carbonyl forms hydrazones. Treatment of benzylideneacetone with the Grignard reagent methyl magnesium bromide followed by acid-induced dehydration gives 1-phenyl-1,3-butadiene.[3] It reacts with Fe2(CO)9 to give (benzylideneacetone)Fe(CO)3, a reagent for transferring the Fe(CO)3 unit to other organic molecules.[4]
[edit] Safety
Benzylideneacetone is a skin irritant.
[edit] References
- ^ Claisen, L. “Über die Einwirkung von Aceton auf Furfural und auf Benzaldehyd bei Gegenwart von Alkalilauge” Berichte der deutschen chemischen Gesellschaft 1881, volume 14, p 2468-2471.
- ^ Drake, N. L.; Allen, Jr. P. “Benzalacetone” Organic Syntheses, Collected Volume 1, p.77 (1941)[[1]]
- ^ Grummitt, O.; Becker, E. I. “trans-1-Phenyl-1,3-butadiene” Organic Syntheses, Collected Volume 4, p.771 (1963).
- ^ Knölker, H.-J. "(η4-Benzylideneacetone)tricarbonyliron" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.
