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D206008

Sigma-Aldrich

trans,trans-1,4-Diphenyl-1,3-butadiene

98%

Synonym(s):

β,β′-Bistyryl, DPB

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About This Item

Linear Formula:
C6H5CH=CHCH=CHC6H5
CAS Number:
538-81-8
Molecular Weight:
206.28
Beilstein:
1905939
MDL number:
MFCD00004791
UNSPSC Code:
12352100
PubChem Substance ID:
24893612
NACRES:
NA.22

Assay

98%

form

crystals

bp

350 °C (lit.)

mp

150-152 °C (lit.)

SMILES string

c1ccc(cc1)\C=C\C=C\c2ccccc2

InChI

1S/C16H14/c1-3-9-15(10-4-1)13-7-8-14-16-11-5-2-6-12-16/h1-14H/b13-7+,14-8+

InChI key

JFLKFZNIIQFQBS-FNCQTZNRSA-N

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Application

trans,trans-1,4-Diphenyl-1,3-butadiene can be used as a reactant to synthesize:
  • 2,5-diphenylthiophene by oxidation reaction with potassium sulfide and DMSO.
  • 2-[(3E)-4-Phenyl-2-(phenylmethyl)-3-buten-1-yl]furan via nickel catalyzed hydrobenzylation reaction with furfural in the presence of N2H4.

It can also be used as a ligand to prepare silver(I) coordination polymers by reacting with silver(I) salts.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nickel-catalyzed regioselective hydrobenzylation of 1, 3-dienes with hydrazones
Lv Leiyang, et al.
ACS Catalysis, 9(10), 9199-9205 (2019)
Liang Chen et al.
Organic letters, 20(23), 7392-7395 (2018-11-22)
A novel, atom economical, and transition-metal-free strategy for the synthesis of thiophenes from substituted buta-1-enes with potassium sulfide has been presented. The reaction achieves double C-S bond formations via cleavage of multiple C-H bonds and provides an efficient approach to
David P Burgner et al.
PloS one, 10(5), e0125342-e0125342 (2015-05-06)
Pathogen-specific and overall infection burden may contribute to atherosclerosis and cardiovascular disease (CVD), but the effect of infection severity and timing is unknown. We investigated whether childhood infection-related hospitalisation (IRH, a marker of severity) was associated with subsequent adult CVD
Syntheses and structural studies on silver (I) coordination polymers with trans, trans-1, 4-dipenyl-1, 3-butadiene
Zhong JC, et al.
Inorganica chimica acta, 342, 202-208 (2003)
Mustafa Toprakçí et al.
Bioorganic & medicinal chemistry letters, 15(20), 4438-4446 (2005-09-03)
Monoamine oxidase (EC1.4.3.4; MAO) is a mitochondrial outer membrane flavoenzyme that catalyzes the oxidation of biogenic amines. It has two distinct isozymic forms designated MAO-A and MAO-B, each displaying different substrate and inhibitor specificities. They are the well-known targets for
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