4-phenyl-3-buten-2-one

Structural formula
General
Surname	4-phenyl-3-buten-2-one
other names	(3 E ) -4-phenyl-3-buten-2-one ( IUPAC ) ; 4-phenylbutenone; Benzylidene acetone; Benzalacetone; Methyl styryl ketone;
Molecular formula	C 10 H 10 O
Brief description	light yellow solid with a characteristic odor
External identifiers / databases
EC number	217-587-6
ECHA InfoCard	100,015,989
PubChem	637759
ChemSpider	21106584
Wikidata	Q4380955
properties
Molar mass	146.19 g mol −1
Physical state	firmly
density	1.008 g cm −3
Melting point	38-41 ° C
boiling point	261 ° C
solubility	sparingly soluble in water (1.3 g l −1 at 20 ° C); miscible with ethanol , benzene , chloroform and diethyl ether ;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-317
	P: 280
Toxicological data	2030 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4-Phenyl-3-buten-2-one (benzylidene acetone) is a chemical compound from the group of ketones .

Occurrence

4-Phenyl-3-buten-2-one occurs naturally in soybeans and Virginia tobacco .

Extraction and presentation

4-Phenyl-3-buten-2-one can be obtained by reacting acetone with benzaldehyde in the presence of sodium hydroxide ( Claisen-Schmidt condensation ).

properties

4-Phenyl-3-buten-2-one is a flammable, hardly ignitable, light yellow solid with a characteristic odor (smell of coumarin ), which is sparingly soluble in water. trans -4-phenyl-3-buten-2-one is a substrate for glutathione-S-transferases . It reacts with methyl and benzylguanidines to form aromatic N ² -substituted 2-pyrimidinamines.

use

Due to its enone substructure, 4-phenyl-3-buten-2-one is used in organic synthesis as a building block for condensation , cycloaddition , Michael additions and Grignard reactions . With diiron nonacarbonyl [Fe ₂ (CO) ₉ ] it provides benzylidene iron tricarbonyl, a reagent that can transfer the Fe (CO) ₃ group to other molecules . Benzalacetone is used as a starting material for the synthesis of warfarin .

safety instructions

4-Phenyl-3-buten-2-one must not be used in the manufacture or treatment of cosmetic products (German Cosmetics Ordinance Annex 1, No. 356).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 4-phenyl-3-buten-2-one in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ ^a ^b Data sheet 4-Phenyl-3-buten-2-one, 99% from Sigma-Aldrich , accessed on January 18, 2016 ( PDF ).
↑ George A. Burdock: Fenaroli's Handbook of Flavor Ingredients, Sixth Edition . CRC Press, 2009, ISBN 978-1-4200-9086-4 ( limited preview in Google Book Search).
↑ Drake, NL; Allen, Jr. P .: Benzalacetone In: Organic Syntheses . 3, 1923, p. 17, doi : 10.15227 / orgsyn.003.0017 ( PDF ).
↑ ^a ^b ^c Entry on benzylidene acetone. In: Römpp Online . Georg Thieme Verlag, accessed on January 18, 2016.
↑ Enders, E .: Rodenticides . In: Wegler, R. (Ed.): Chemistry of pesticides and pesticides. 1st edition. tape 1 . Springer, Berlin / Heidelberg / New York 1970, pp. 618 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 4-phenyl-3-buten-2-one in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[Sigma-2] Data sheet 4-Phenyl-3-buten-2-one, 99% from Sigma-Aldrich , accessed on January 18, 2016 ( PDF ).

[3] George A. Burdock: Fenaroli's Handbook of Flavor Ingredients, Sixth Edition . CRC Press, 2009, ISBN 978-1-4200-9086-4 ( limited preview in Google Book Search).

[4] Drake, NL; Allen, Jr. P .: Benzalacetone In: Organic Syntheses . 3, 1923, p. 17, doi : 10.15227 / orgsyn.003.0017 ( PDF ).

[RömppOnline-5] Entry on benzylidene acetone. In: Römpp Online . Georg Thieme Verlag, accessed on January 18, 2016.

[6] Enders, E .: Rodenticides . In: Wegler, R. (Ed.): Chemistry of pesticides and pesticides. 1st edition. tape 1 . Springer, Berlin / Heidelberg / New York 1970, pp. 618 .