Benzylideneacetone

Benzylideneacetone
Names
Preferred IUPAC name
(3E)-4-Phenylbut-3-en-2-one
Other names
Benzalacetone
Benzylideneacetone
Methyl styryl ketone
Benzylidene acetone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.015.989 Edit this at Wikidata
EC Number
  • 204-555-1 (trans)
RTECS number
  • EN0330000
UNII
  • InChI=1S/C10H10O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8H,1H3/b8-7+ checkY
    Key: BWHOZHOGCMHOBV-BQYQJAHWSA-N checkY
  • InChI=1/C10H10O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8H,1H3/b8-7+
    Key: BWHOZHOGCMHOBV-BQYQJAHWBQ
  • CC(=O)/C=C/c1ccccc1
Properties
C10H10O
Molar mass 146.19 g/mol
Appearance pale yellow solid
Density 1.008 g/cm3
Melting point 39 to 42 °C (102 to 108 °F; 312 to 315 K)
Boiling point 260 to 262 °C (500 to 504 °F; 533 to 535 K)
1.3 g/L
Solubility in other solvents nonpolar solvents
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 irritant
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H317, H319, H335
P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501
Flash point 116 °C (241 °F; 389 K)
Related compounds
Related compounds
 Dibenzylideneacetone
cinnamaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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] Benzylideneacetone is used as a flavouring ingredient in food and perfumes.[2]

  1. ^ 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.
  2. ^ Opdyke, D. L. J. (2013). Monographs on Fragrance Raw Materials: A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology. Elsevier. p. 135. ISBN 9781483147970.