1608-10-2

Basic information

• Product Name: (1E,3E)-1,2,3,4-Tetraphenyl-1,3-butadiene
• Synonyms: (1E,3E)-1,2,3,4-Tetraphenyl-1,3-butadiene
• CAS NO: 1608-10-2
• Molecular Formula: C₂₈H₂₂
• Molecular Weight: 358.47
• Mol File: 1608-10-2.mol
• Article Data: 31

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1E,3E)-1,2,3,4-Tetraphenyl-1,3-butadiene(CAS DataBase Reference)
• NIST Chemistry Reference: (1E,3E)-1,2,3,4-Tetraphenyl-1,3-butadiene(1608-10-2)
• EPA Substance Registry System: (1E,3E)-1,2,3,4-Tetraphenyl-1,3-butadiene(1608-10-2)

Safety Data

• Hazardous Substances Data: 1608-10-2(Hazardous Substances Data)

Usage

General Description

(1E,3E)-1,2,3,4-Tetraphenyl-1,3-butadiene is a chemical compound with the molecular formula C28H22. It consists of a linear hydrocarbon chain with alternating single and double bonds, and is substituted with four phenyl groups. (1E,3E)-1,2,3,4-Tetraphenyl-1,3-butadiene is known for its high conjugation, which makes it useful in various organic synthesis reactions and materials science applications. It is commonly used as a building block in the synthesis of larger organic molecules, such as coordination compounds and polymers, due to its high reactivity and stability. Additionally, its extended pi-conjugated structure makes it a promising candidate for optoelectronic devices and organic semiconductors.

Upstream product

• 2789-88-0 1,2-bis(4-methylphenyl)acetylene 
• 501-65-5 diphenyl acetylene 
• 26305-75-9 chlorotris(triphenylphosphine)cobalt(I) 
• 73183-34-3 bis(pinacol)diborane 
• 1123-11-1 cyclonona-1,2-diene 
• 563-43-9 ethylaluminum dichloride 
• 19816-85-4 N'-(1,2-diphenylethylidene)-4-methylbenzenesulfonohydrazide 
• 21289-08-7 (E,E)-(1,2,3,4-tetramethyl-1,3-butadien-1,4-ylidene)-dilithium 
• 109-72-8 n-butyllithium 
• 1291-32-3 zirconocene dichloride 
• 1271-19-8 bis(cyclopentadienyl)titanium dichloride 
• 632-51-9 1,1,2,2-tetraphenylethylene 
• 134-81-6 benzil 
• 7381-16-0 1,2-disodiotetraphenylethane 

Downstream Products

• 2067-93-8 1-benzylidene-2,3-diphenyl-1H-indene 
• 5271-40-9 meso-1,2,3,4-tetraphenylbutane 
• 1884-68-0 tetraphenylthiophene 
• 872269-87-9 1-benzylidene-2,3-diphenyl-indan 
• 91861-68-6 5,10-diphenyl-5,10-dihydro-indeno[2,1-a]indene 
• 67961-34-6 3-benzyl-1,2-diphenyl-1H-indene 
• 5773-56-8 1,2-Diphenylethanol 
• 806-69-9 1,2,3,4-tetraphenylbutane 
• 7474-65-9 (E)-2-phenylchalcone 
• 55255-19-1 1,2,3,4-tetraphenyl-2-butene 
• 1687-94-1 5,10-diphenyldibenzopentalene 
• 55255-18-0 1,2,3,4-tetraphenyl-2-butene 
• 55255-22-6 9,14-dihydro-9-phenyldibenz[a,c]anthracene 
• 55255-21-5 1,2,3-triphenyl-1,4-dihydro-naphthalene 

Relevant articles and documents

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Selective preparation of 1,3-butadienyl phosphines, 1-iodo- and 1,4-diiodo-butadienyl phosphine oxides via zirconocene-mediated cross-coupling of alkynylphosphines

Stereodefined butadienyl phosphines and related derivatives were readily prepared in high yields with perfect regioselectivity via the zirconocene-mediated pair-selective coupling of alkynylphosphines with ethylene or alkynylphosphines with normal alkynes

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The crystal structure of [Mo(NCS)(CO)2(η3-C3H5) (NCMe)2].MeCN and the reactions of {Mo(CO)2 (η3-C3H5)+} containing species with symmetric alkynes

In the solid-state about molybdenum, with carbonyls and nitriles in the equatorial plane and an N-bonded thiocyanate group trans to the allyl ligand. In refluxing methanol or acetonitrile both 1, and the analogous chloro-complex [MoCl(CO)2(η3-C3 H5)(NCMe)2](2) catalytically convert PhC≡CPh to a mixture of hexaphenylbenzene and E,E-1,2,3,4-tetraphenylbutadiene. By contrast MeO2CC≡CCO2Me is not oligomerised. In methanol, complex 2 dimerises 1,4-diphenylbutadiyne to Z,E-1,4,5,8-tetraphenyl-1,7-octa-3,5-diene-1,7-diyne, whereas in the presence of base both the complex and the diyne, react preferentially with the solvent to generate the [Mo2(CO)4 (η3-C3H5)2 (OMe)3]- anion and Z-1,4-diphenyl-3- methoxy-but-3-ene-1-yne, respectively.

Aggregation-induced emission of cis,cis-1,2,3,4-tetraphenylbutadiene from restricted intramolecular rotation

cis,cis-1,2,3,4-Tetraphenylbutadiene (TPBD) exhibits aggregation-induced emission (AIE) in the UV-blue band: the photoluminescence (PL) quantum yield of TPBD aggregates can differ from that of molecularly dissolved species by 2 orders of magnitude (>200).

Nickel-Catalyzed Reductive [2+2] Cycloaddition of Alkynes

The nickel-catalyzed synthesis of tetrasubstituted cyclobutenes from alkynes is reported. This transformation is uniquely promoted by the use of a primary aminophosphine, an unusual ligand in nickel catalysis. Mechanistic insights for this new transformation are provided, and postreaction modifications of the cyclobutene products to stereodefined cyclic and acyclic compounds are reported, including the synthesis of epi-truxillic acid.

Pd-catalyzed cross-coupling reactions of hydrazones: Regioselective synthesis of highly branched dienes

The regioselective formation of highly branched dienes is a challenging task. Design and exploration of alternative working models to achieve such a regioselectivity to accomplish highly branched dienes is considered to be a historical advancement of Heck reaction to construct branched dienes. On the basis of the utility of carbene transfer reactions, in the reaction of hydrazones with Pd(II) under oxidative conditions, we envisioned obtaining a Pd-bis-carbene complex with α-hydrogens, which can lead to branched dienes. Herein, we report a novel Pd-catalyzed selective coupling reaction of hydrazones in the presence of t-BuOLi and benzoquinone to form the corresponding branched dienes. The utility of the Pd catalyst for the cross-coupling reactions for synthesizing branched conjugated dienes is rare. The reaction is very versatile and compatible with a variety of functional groups and is useful in synthesizing heterocyclic molecules. We anticipate that this Pd-catalyzed cross-coupling reaction will open new avenues for synthesizing useful compounds.