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
- Molecular Weight:
- 234.29
- MOL File:
- 538-58-9.mol
- Modify Date:
- 2024/7/8 20:25:11
| 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) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
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|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302-H315-H317-H319-H335-H413 | |||||||||
| Precautionary statements | P261-P280-P305+P351+P338 | |||||||||
| Safety Statements | 22-24/25 | |||||||||
| WGK Germany | 3 | |||||||||
| HS Code | 2914790090 | |||||||||
| NFPA 704 |
|
Dibenzylideneacetone Chemical Properties,Uses,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
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Sam Research Labs | +91 9873930190 | Hyderabad, India | 219 | 58 | Inquiry |
| Alchem Synthon Pvt Ltd | +919320089706 | Maharashtra, India | 36 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| Infinity Speciality Chemicals | 08048372823Ext 965 | Mumbai, India | 12 | 58 | Inquiry |
| CHEMSWORTH | +91-261-2397244 | New Delhi, India | 6707 | 30 | Inquiry |
| Organo Fine Chemicals | +91 (22) 2201-6968 / 2206-7521 | New Delhi, India | 266 | 60 | Inquiry |
| Xi'an Tuochao Biotechnology Co., Ltd | +86-02988764766 +86-18092957403 | China | 110 | 58 | Inquiry |
| PUSHAN INDUSTRIAL (SHAANXI) CO.,LTD | +8618291886785 | China | 144 | 58 | Inquiry |
| Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | China | 29798 | 60 | Inquiry |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | China | 21671 | 55 | Inquiry |
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