Benzylideneacetone

Title: Benzylideneacetone
CAS Registry Number: 122-57-6
CAS Name: 4-Phenyl-3-buten-2-one
Additional Names: benzalacetone; methyl styryl ketone; cinnamyl methyl ketone; acetocinnamone
Molecular Formula: C10H10O
Molecular Weight: 146.19
Percent Composition: C 82.16%, H 6.89%, O 10.94%
Line Formula: C6H5CH=CHCOCH3
Literature References: Prepd by condensing acetone and benzaldehyde by means of aq alkali: Drake, Allen, Org. Synth. 3, 17 (1923).
Properties: Lustrous plates on vacuum distillation. Coumarin type odor. Purification by steam distillation: Fromm, Haas, Ann. 394, 291 (1912). mp 41.5°. d1515 1.0377; d445.2 1.0097. bp760 261°; bp200 211°; bp100 187.8°; bp40 161.3°; bp20 143.8°; bp10 127.4°; bp5 112.2°; bp1.0 81.7°. nD45.9 1.5836. Absorption spectrum: Baker, J. Chem. Soc. 91, 1492 (1907); Baly, Schafer, ibid. 93, 1813 (1908). Freely sol in alcohol, benzene, chloroform, ether; sparingly sol in water, petr ether.
Melting point: mp 41.5°
Boiling point: bp760 261°; bp200 211°; bp100 187.8°; bp40 161.3°; bp20 143.8°; bp10 127.4°; bp5 112.2°; bp1.0 81.7°
Index of refraction: nD45.9 1.5836
Density: d1515 1.0377; d445.2 1.0097
Use: In perfumery, organic syntheses.
Benzylideneaniline Benzylimidobis(p-methoxyphenyl)methane Benzylmorphine Benzylsulfamide Benzylurea

Benzylideneacetone
Benzylideneacetone-2D-skeletal.png
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Identifiers
CAS number 122-57-6 YesY, 1896-62-4 (trans)
ChemSpider 21106584 YesY
ChEBI CHEBI:217301 YesY
ChEMBL CHEMBL73639 YesY
RTECS number EN0330000
Jmol-3D images Image 1
Properties
Molecular formula C10H10O
Molar mass 146.19 g/mol
Appearance pale yellow solid
Density 1.008 g/cm3
Melting point 39–42 °C
Boiling point 260–262 °C
Solubility in water 1.3 g/L
Solubility in other solvents nonpolar solvents
Hazards
R-phrases 36/37/38-43
S-phrases 22-26-36/37
Main hazards irritant
Flash point 116 °C; 241 °F; 389 K
Related compounds
Related compounds Dibenzylideneacetone
cinnamaldehyde
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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]