ChemicalBook > CAS DataBase List > Dibenzylideneacetone

Dibenzylideneacetone

Product Name
Dibenzylideneacetone
CAS No.
538-58-9
Chemical Name
Dibenzylideneacetone
Synonyms
DIBENZAL ACETONE;1,5-DIPHENYL-1,4-PENTADIEN-3-ONE;AKOS 213-33;DISTYRYL KETONE;1,3-Dibenzylideneacetone;TRANS,TRANS-DIBENZALACETONE;1,4-Pentadien-3-one, 1,5-diphenyl-;(1Z,4E)-1,5-diphenylpenta-1,4-dien-3-one;TRANS,TRANS-1,5-DIPHENYL-1,4-PENTADIEN-3-ONE;Nsc8103
CBNumber
CB3705221
Molecular Formula
C17H14O
Formula Weight
234.29
MOL File
538-58-9.mol
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Dibenzylideneacetone Property

Melting point:
107-113 °C
Boiling point:
336.62°C (rough estimate)
Density 
1.0477 (rough estimate)
refractive index 
1.5000 (estimate)
storage temp. 
Sealed in dry,Room Temperature
form 
solid
color 
yellow
Stability:
Stable. Incompatible with strong oxidizing agents. Combustible.
InChIKey
WMKGGPCROCCUDY-UHFFFAOYSA-N
CAS DataBase Reference
538-58-9(CAS DataBase Reference)
EPA Substance Registry System
1,4-Pentadien-3-one, 1,5-diphenyl- (538-58-9)
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Safety

Safety Statements 
22-24/25
WGK Germany 
3
HS Code 
2914790090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H335May cause respiratory irritation

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
S676985
Product name
1,5-DIPHENYL-1,4-PENTADIEN-3-ONE
Purity
Aldrich
Packaging
250mg
Price
$179
Updated
2024/03/01
Strem Chemicals
Product number
08-0625
Product name
1,5-Diphenyl-1,4-pentadien-3-one, min. 98% (Dibenzylideneacetone)
Packaging
1g
Price
$70
Updated
2024/03/01
Strem Chemicals
Product number
08-0625
Product name
1,5-Diphenyl-1,4-pentadien-3-one, min. 98% (Dibenzylideneacetone)
Packaging
5g
Price
$278
Updated
2024/03/01
AK Scientific
Product number
CS-M0452
Product name
1,5-Diphenylpenta-1,4-dien-3-one
Packaging
50g
Price
$80
Updated
2021/12/16
ChemScene
Product number
CS-M0452
Product name
1,5-Diphenylpenta-1,4-dien-3-one
Packaging
500g
Price
$158
Updated
2021/12/16
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Dibenzylideneacetone Chemical Properties,Usage,Production

Chemical Properties

trans,trans-Dibenzylideneacetone is a crystalline solid, melting point 110-111℃; cis-trans is a light yellow needle crystal, melting point 60℃; cis-cis is a yellow oily liquid, boiling point 130℃ (2.7Pa). Soluble in ethanol, acetone, chloroform, insoluble in water.

Uses

Dibenzylideneacetone is used as a ligand to prepare palladium catalysts, which are widely used in catalytic hydrogenation, coupling, carbonylation, alkyne ring trimerization, etc.

Preparation

Dibenzylideneacetone is obtained by the reaction of benzaldehyde and acetone. The reaction was carried out in aqueous ethanol solution at a reaction temperature of 20-25°C with a yield of 78%.

Synthesis Reference(s)

Chemistry Letters, 9, p. 51, 1980
The Journal of Organic Chemistry, 45, p. 3840, 1980 DOI: 10.1021/jo01307a022
Organic Syntheses, Coll. Vol. 2, p. 167, 1943

Biological Activity

Dibenzylideneacetone (DBA) showed inhibitory activity against Botrytis cinerea Chitinase with an IC50 of 13.10 μg/mL. The MIC of DBA against B. cinerea was 32 μg/mL, and the EC50 values for inhibition of hyphae growth and spore germination were 16.29 and 14.64 μg/mL, respectively. DBA was able to significantly extend the shelf life of cherry tomato shelf life and is a promising antifungal agent for fruit preservation[1].

Purification Methods

Crystallise the ketone from hot ethyl acetate (2.5mL/g) or EtOH. [Beilstein 7 IV 1747.]

References

[1] XIAODI NIU; Chenyang W; Ziyou Wang, HONGSU WANG*. Dibenzylideneacetone Overcomes Botrytis cinerea Infection in Cherry Tomatoes by Inhibiting Chitinase Activity[J]. Journal of Agricultural and Food Chemistry, 2023. DOI:10.1021/acs.jafc.3c05695.

Dibenzylideneacetone Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Dibenzylideneacetone manufacturers

PUSHAN INDUSTRIAL (SHAANXI) CO.,LTD
Product
Dibenzylideneacetone 538-58-9
Price
US $0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
500 kgs
Release date
2024-07-08
Career Henan Chemical Co
Product
DIBENZYLIDENEACETONE 538-58-9
Price
US $1.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
Customized
Release date
2018-12-17

538-58-9, DibenzylideneacetoneRelated Search:

Tris(dibenzylideneacetone)dipalladium CALCIUM OXIDE Titanous chloride Benzylacetone trans,trans-Dibenzylideneacetone TRIS(DIBENZYLIDENEACETONE)DIPLATINUM(0), 99,Bis(dibenzylideneacetone)platinum(0)~Ptdba Bis(dibenzylideneacetone)palladium Tris(dibenzylideneacetone)dipalladium-chloroform adduct Tris(dibenzylideneacetone)dipalladium Tris(dibenzylideneacetone)dipalladium Tris[dibenzylideneacetone]dipalladium(0)-S-Phos (Pd:P 1:2), ChemDose(R) tablets Palladium dibenzylideneacetone Tris(dibenzylideneacetone)dipalladium(0)/tri-t-butylphosphonium tetrafluoroborate admixture (molar Pd/P = 1:1.2) DIBENZYLIDENEACETONE, (1,5-DIPHENYLPENTA-1,4-DIEN-3-ONE) trans,trans-1,4-Dibenzylideneacetone TRIS(DIBENZYLIDENEACETONE)DIPLATINUM(0) Tris(dibenzylideneacetone)dipalladium(0)/tri-t-butylphosphonium tetrafluoroborate admixture (molar Pd/P = 1:2) Dibenzylideneacetone bis(triphenylphosphine)palladium(0), polymer-bound

  • DIBENZYLIDENEACETONE
  • DIBENZAL ACETONE
  • DISTYRYL KETONE
  • 1,5-DIPHENYL-PENTA-1,4-DIEN-3-ONE
  • 1,5-DIPHENYL-3-PENTADIENONE
  • 1,5-DIPHENYL-1,4-PENTADIEN-3-ONE
  • 1,5-Diphenyl-1,4-pentadien-3-one, min. 98%
  • AKOS 213-33
  • 1,5-Diphenyl-1,4-pentadien-3-one (Dibenzylideneacetone)
  • TRANS,TRANS-1,5-DIPHENYL-1,4-PENTADIEN-
  • 1,5-Diphenyl-3-Pentadieneone
  • Dibenzylideneacetone, 98+%
  • 1,3-Dibenzylideneacetone
  • Di(2-phenylvinyl) ketone
  • 1,5-Diphenyl-1,4-pentadien-3-one, Min. 98% (Dibenzylideneacetone)
  • Nsc8103
  • ((1Z,4E)-3-Methylenepenta-1,4-diene-1,5-diyl)dibenzene
  • TRANS,TRANS-1,5-DIPHENYL-1,4-PENTADIEN-3-ONE
  • TRANS,TRANS-1,5-DIPHENYLPENTA-1,4-DIEN-3-ONE
  • TRANS,TRANS-DIBENZALACETONE
  • TRANS,TRANS-DISTYRYL KETONE
  • (1E,4E)-1,5-Diphenyl-1,4-pentadien-3-one
  • 1,4-Pentadien-3-one, 1,5-diphenyl-
  • 1,5-Diphenyl-1,4-pentadiene-3-one
  • 1,5-diphenyl-4-pentadien-3-one
  • Bis(2-phenylvinyl) ketone
  • Styrol ketone
  • (4E)-1,5-diphenyl-3-penta-1,4-dienone
  • (1Z,4E)-1,5-diphenylpenta-1,4-dien-3-one
  • DIBENZYLIDENEACETONE
  • 538-58-9
  • Organic Building Blocks
  • Ketones
  • C15 to C38
  • Carbonyl Compounds
  • Building Blocks
  • Achiral Oxygen