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538-58-9 molecular structure
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(4E)-1,5-diphenylpenta-1,4-dien-3-one

ChemBase ID: 78682
Molecular Formular: C17H14O
Molecular Mass: 234.29246
Monoisotopic Mass: 234.10446507
SMILES and InChIs

SMILES:
O=C(/C=C/c1ccccc1)/C=C/c1ccccc1
Canonical SMILES:
O=C(/C=C/c1ccccc1)/C=C/c1ccccc1
InChI:
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
InChIKey:
WMKGGPCROCCUDY-UHFFFAOYSA-N

Cite this record

CBID:78682 http://www.chembase.cn/molecule-78682.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(4E)-1,5-diphenylpenta-1,4-dien-3-one
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one
1,5-diphenylpenta-1,4-dien-3-one
IUPAC Traditional name
(4E)-1,5-diphenylpenta-1,4-dien-3-one
dibenzylideneacetone
Synonyms
DISTYRYL KETONE
DIBENZAL ACETONE
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one
Dibenzalacetone
Dibenzylideneacetone
1,5-Diphenyl-1,4-pentadien-3-one
trans,trans-1,5-Diphenyl-1,4-pentadien-3-one
trans,trans-Dibenzylideneacetone
Dibenzylideneacetone
1,5-Diphenylpenta-1,4-dien-3-one
(E,E)-1,5-Diphenyl-1,4-pentadien-3-one
1,5-二苯-1,4-戊二烯-3-酮
反,反-二亚苄基丙酮
联甲基苯乙烯酮
反式,反式-二亚苄基丙酮
CAS Number
538-58-9
35225-79-7
EC Number
208-697-5
MDL Number
MFCD00004790
Beilstein Number
608434
Merck Index
143006
PubChem SID
24854806
162043445
24867016
PubChem CID
1549622
640180
Chemspider ID
1266463
Wikipedia Title
Dibenzylideneacetone

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 4.825144  LogD (pH = 7.4) 4.825144 
Log P 4.825144  Molar Refractivity 77.0272 cm3
Polarizability 28.964622 Å3 Polar Surface Area 17.07 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Insoluble in water expand Show data source
Apperance
Yellow solid expand Show data source
Melting Point
*Aldrich 110-111 oC (trans,trans isomer)
*Merck 60 °C (cis,trans isomer)
expand Show data source
104-107 °C(lit.) expand Show data source
107-113 °C expand Show data source
112-114°C expand Show data source
Boiling Point
130 °C (cis,cis isomer) *Merck expand Show data source
Storage Warning
Irritant expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
expand Show data source
Main Hazard
Irritant expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥98.0% (HPLC) expand Show data source
95+% expand Show data source
97% expand Show data source
98% expand Show data source
98+% expand Show data source
Certificate of Analysis
Download expand Show data source
Linear Formula
C6H5CH=CHCOCH=CHC6H5 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 246425 external link
Packaging
10, 50 g in poly bottle
Application
Reactant involved in:
• Nazarov-like cyclization1
• Transfer hydrogenation2
• Lewis acid mediated condensation3
• Hetero-Diels-Alder reactions4
• Asymmetric 1,4-addition reactions5
• Michael addition reactions6
Sigma Aldrich - 43143 external link
Other Notes
This reactive dienone readily forms carbo- or heterocyclic compounds with many nucleophiles.; Dibenzylideneacetone forms a stable zero-valent, neutral complex with palladium(0), Pd(dba)27; Preparation of Pd2(dba)3(solvent) complexes8; These palladium(0)-dibenzylideneacetone complexes are important catalysts9;
Packaging
10 g in glass bottle
Application
Reactant involved in:
• Nazarov-like cyclization1
• Transfer hydrogenation2
• Lewis acid mediated condensation3
• Hetero-Diels-Alder reactions4
• Asymmetric 1,4-addition reactions5
• Michael addition reactions6

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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