43143
trans,trans-Dibenzylideneacetone
≥98.0% (HPLC)
Synonym(s):
1,5-Diphenyl-1,4-pentadien-3-one, trans,trans-1,5-Diphenyl-1,4-pentadien-3-one
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About This Item
Linear Formula:
C6H5CH=CHCOCH=CHC6H5
CAS Number:
Molecular Weight:
234.29
UNSPSC Code:
12352100
PubChem Substance ID:
MDL number:
assay
≥98.0% (HPLC)
mp
104-107 °C (lit.), 107-113 °C
solubility
dichloromethane: soluble 25 mg/mL, clear
SMILES string
O=C(\C=C\c1ccccc1)/C=C/c2ccccc2
InChI
1S/C17H14O/c18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16/h1-14H/b13-11+,14-12+
InChI key
WMKGGPCROCCUDY-PHEQNACWSA-N
General description
trans,trans-Dibenzylideneacetone (dba) participates as an additive in the copper-catalyzed N-arylation of imidazoles. dba acts as ligand. It has an important influence on the reactivity of palladium(0) complexes generated in situ from the mixtures of Pd(dba)2 and phosphine ligands. Photolysis of trans,trans-dibenzylideneacetone (1,5-diphenylpenta-1,4-dien-3-one) in benzene solution affords the truxinic-type dimer. It is a reactive dienone and readily forms carbo- or heterocyclic compounds with many nucleophiles. Dibenzylideneacetone forms a stable zero-valent, neutral complex with palladium(0), Pd(dba)2. It also participates in the preparation of Pd2(dba)3(solvent) complexes. These palladium(0)-dibenzylideneacetone complexes are important catalysts.
Application
Reactant involved in:
- Nazarov-like cyclization
- Transfer hydrogenation
- Lewis acid mediated condensation
- Hetero-Diels-Alder reactions
- Asymmetric 1,4-addition reactions
- Michael addition reactions
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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M.F. Rettig et al.
Inorg. Synth., 17, 134-134 (1977)
J. Tsuji
Organic Synthesis with Palladium Compounds (1980)
T. Ukai et al.
Journal of Organometallic Chemistry, 65, 253-253 (1974)
An efficient copper-catalyzed coupling of aryl halides with imidazoles.
Kiyomori A, et al.
Tetrahedron Letters, 40(14), 2657-2660 (1999)
Role of dba in the reactivity of palladium (0) complexes generated in situ from mixtures of Pd (dba)2 and phosphines.
Amatore C and Jutand A.
Coordination Chemistry Reviews, 178, 511-528 (1998)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 20025-25ML | 04061838125453 |
| 20025-5ML | 04061838118516 |
| 20025-1ML | 04061838125446 |
| 728411-100ML | 04061838069962 |
| 728411-25ML | 04061838103154 |
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