(1E,4E)-1,5-Diphenyl-1,4-pentadien-3-one
Basic information
- CAS
35225-79-7- Standard SMILES
O=C(/C=C/c1ccccc1)/C=C/c1ccccc1- InChIKey
WMKGGPCROCCUDY-PHEQNACWSA-N- Molecular formula
- C17H14O
- Average molar mass
- 234.29 g/mol
- Monoisotopic mass
- 234.10446507
Overview
Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is an organic compound with the formula C17H14O. It is a bright-yellow solid insoluble in water, but soluble in ethanol. Dibenzylideneacetone is used as a sunscreen component and as a ligand in organometallic chemistry, for instance in tris(dibenzylideneacetone)dipalladium(0). In this case, it is a labile ligand that is easily displaced by stronger ligands like triphenylphosphine, hence it serves a useful entry point into palladium(0) chemistry. (L2096)
Names & identifiers
- Preferred name
- (1E,4E)-1,5-Diphenyl-1,4-pentadien-3-one
- IUPAC
- (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one
- English name
- trans,trans-Dibenzylideneacetone
- Molecular formula
- C17H14O
- Molecular weight
- 234.29
Names & synonyms
35225-79-7trans,trans-DibenzylideneacetoneDibenzalacetoneDistyryl ketone1,5-Diphenyl-1,4-pentadien-3-one(1E,4E)-1,5-Diphenyl-1,4-pentadien-3-one9QXO7BCY9L1,4-Pentadien-3-one, 1,5-diphenyl-, (E,E)-NSC-117234DTXSID401274418RefChem:1049387DTXCID70210790
Show more names
DIBENZAL ACETONEAKOS 213-33Dibenzylidineacetone DBAtrans,trans-Dibenzylideneacetone 98%Dibenzylideneacetontrans,trans-DibenzyLDibenzylideneacetone ,99%
208-697-5Dibenzylideneacetone(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one538-58-9trans,trans-Dibenzalacetone1,4-Pentadien-3-one, 1,5-diphenyl-, (1E,4E)-trans,trans-1,5-Diphenyl-1,4-pentadien-3-oneDibenzalacetone [MI]
Database identifiers
- CAS
35225-79-7、538-58-9- PubChem CID
- 640180
- DTXSID
DTXSID401274418
Properties
Computed structural properties
- XLogP
- 4.1
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 4
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 272
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Aromatic Ketones
Physical DescriptionSolid; [Merck Index] Yellow crystalline powder; [Acros Organics MSDS]
Physicochemical properties
- Melting point
- 104 · 104-107 °C (lit.)
- Boiling point
- 336.62 °C · 336.62°C (rough estimate)
- Density
- 1.0477 · 1.0477 (rough estimate)
- refractive index
- 1.5 · 1.5000 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- acetone: soluble(lit.)
- form
- Crystalline Powder
- color
- Yellow
- Water Solubility
- Soluble in chloroform, acetone, alcohol (slightly), and hot methanol. Insoluble in water.
- Merck
- 14 · 14,3006
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationChemical: 1,4-Pentadien-3-one, 1,5-diphenyl-
Hazards SummaryMay cause irritation; [Acros Organics MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxicology
Health EffectsDibenzylideneacetone is an irritant.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29143990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
Chemistry & industry
Uses & manufacturing
Uses
Used in sun protection products; [Merck Index]
Dibenzylideneacetone is used as a sunscreen component and as a ligand in organometallic chemistry. (L2096)
General Manufacturing Information1,4-Pentadien-3-one, 1,5-diphenyl-: ACTIVE
Applications
Usestrans,trans-Dibenzylideneacetone was used as an additive in the copper-catalyzed-arylation of imidazoles. It is a reactant involved in Nazarov-like cyclization, Transfer hydrogenation, Lewis acid mediated condensation, Hetero-Diels-Alder reactions, Asymmetric 1,4-addition reactions and Michael addition reactions.
Upstream & downstream products
Upstream raw materials
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Compound notes
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