538-81-8

Usage

Uses

Used in Chemical Synthesis:
TRANS,TRANS-1,4-DIPHENYL-1,3-BUTADIENE is used as a chemical intermediate for the synthesis of various organic compounds. Its conjugated diene system allows it to participate in reactions such as Diels-Alder reactions, which are widely used in the construction of complex organic molecules.
Used in Metal-Diene Reagent Preparation:
TRANS,TRANS-1,4-DIPHENYL-1,3-BUTADIENE is used as a reactant for the preparation of metal-diene reagents, specifically with Rieke metal complexes of barium and strontium. These metal-diene reagents are valuable in the field of organic chemistry, as they are used for carbocyclization reactions with dichloroalkanes. The carbocyclization process is an important synthetic method for constructing cyclic carbon frameworks, which are found in many biologically active compounds and pharmaceuticals.
Used in Pharmaceutical Industry:
TRANS,TRANS-1,4-DIPHENYL-1,3-BUTADIENE, due to its unique chemical structure and reactivity, can be used in the pharmaceutical industry as a building block for the synthesis of various drug candidates. Its ability to participate in a range of chemical reactions makes it a versatile starting material for the development of new therapeutic agents.
Used in Material Science:
The conjugated diene system in TRANS,TRANS-1,4-DIPHENYL-1,3-BUTADIENE also makes it a potential candidate for use in the development of advanced materials, such as polymers and plastics. Its unique electronic properties could be exploited to create materials with specific optical, electronic, or mechanical characteristics, which could find applications in various industries, including electronics, automotive, and aerospace.

Purification Methods

Its solution in pet ether (b 60-70o) is chromatographed on an alumina-Celite column (4:1), and the column is washed with the same solvent. The main zone is cut out, eluted with ethanol and transferred to pet ether, which is then dried and evaporated [Pinckard et al. J Am Chem Soc 70 1938 1948]. Recrystallise it from hexane. [Beilstein 5 H 676, 9 IV 2319.]

InChI:InChI=1/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+

Synthetic route

C16H14(1-) (538-81-8, 886-65-7, 5807-76-1, 5808-05-9, 72777-78-7, 82336-16-1, 82598-07-0, 118493-16-6, 125341-40-4, 129443-78-3) → C16H14 (538-81-8)

Conditions	Yield
With tetrahydrofuran; hydrogen cation Rate constant;
With protonated methyl cyanide Rate constant;

C16H36N(1+)*C16H14(1-) (125341-42-6) → C16H14 (538-81-8)

Conditions	Yield
With tetrahydrofuran; hexafluorophosphoric acid Rate constant;

Upstream product

• 91-22-5 quinoline 
• 588-73-8 (Z)-β-bromostyrene 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 16844-20-5 1,4-dibromo-1,4-diphenyl-butane 
• 56-23-5 tetrachloromethane 
• 1083-56-3 1,4-diphenylbutane 
• 118-75-2 chloranil 
• 65350-60-9 (E)-2-(vinylbenzenesulfonyl)vinylbenzene 
• 100-42-5 styrene 
• 271-89-6 1-benzofurane 
• 677-22-5 tert-butylmagnesium chloride 
• 101933-29-3 (E)-1-nitro-2-(phenylsulfonyl)ethylene 
• 32232-27-2 1,2-diphenylcyclobutene 
• 53446-15-4 1,2,3,4-tetrabromo-1,4-diphenyl-butane 

Downstream Products

• 855288-74-3 phenyl[1, 1’; 4’, 1’’]terphenyl-2’-yl-methanone 
• 56994-68-4 4-nitro-3,5,6-triphenyl-cyclohexene 
• 53991-40-5 diethyl 3,6-diphenyl-1,2,3,6-tetrahydropyridazine-1,2-dicarboxylate 
• 43074-35-7 9-oxo-1,4-bis(phenyl)fluorene 
• 1083-56-3 1,4-diphenylbutane 
• 5808-05-9 (1Z,3E)-1,4-diphenylbuta-1,3-diene 
• 13657-49-3 1,4-diphenylbut-2-ene 
• 6165-44-2 1,4-dicyclohexyl-butane 
• 871874-14-5 2,5-diphenyl-hex-3-enedioic acid 
• 111865-00-0 1,4-diphenyl-but-2-enediyl disodium 
• 54380-72-2 methyl azulene-5-carboxylate 
• 97692-17-6 1,4,5,8-tetraphenyl-anthraquinone 
• 93782-94-6 (+/-)-2t.5t-diphenyl-cyclohexene-⁽³⁾-carboxylic acid-(1r) 
• 93782-94-6 c-2,c-5-diphenyl-3-cyclohexene-r-1-carboxylic acid 

Relevant academic research and scientific papers

A SIMPLE SYNTHESIS OF TRANS, TRANS-1,3-DIENES FROM TERMINAL ALKYNES USING CoCl2/Ph3P/NaBH4

The cobalt hydride reagent prepared in situ in THF at -20 deg C using CoCl2/NaBH4/Ph3P in the 1:1:4 ratio hydrodimerizes terminal alkynes into the corresponding trans, trans-1,3-dienes in good yields (65 to 86percent).

A novel stereoselective synthesis of symmetrical (1E,3E)-1,4-diarylbuta-1, 3-dienes

A convenient methodology for the stereoselective synthesis of symmetrical (1E,3E)-1,4-diarylbuta-1,3-dienes based on palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of (1E,3E)-1,4-diiodobuta-1,3-diene with arylboronic reagents is reported. Georg Thieme Verlag Stuttgart.

Mechanism of a Suzuki-Type Homocoupling Reaction Catalyzed by Palladium Nanocubes

The trans-2-phenylvinylboronic acid homocoupling reaction catalyzed by palladium nanocubes (Pd-NCs) was investigated by kinetics, spectroscopy, and poisoning experiments. The reaction was evidenced to be sensitive to the presence of the base, which acts synergistically with the substrate molecules and assists the leaching of Pd oxide (PdOx) species to the reaction medium. This species catalyzes the homocoupling reaction through the formation of Pd-Ox-B(OH)2R pretransmetalation intermediates, via coordination with the vinylboronic acid molecules, involving an oxo-palladium-type interaction. The reaction rate was not enhanced by the saturation of the reaction medium with O2, which is due to the oxidized nature of the Pd-NC surface.

Efficient Conditions for the Palladium(II) Mediated Coupling of Organostannanes: The Synthesis of 1,3-Dienes, 1,4-Dienes, 1,3-Diynes and Biphenyls

Convenient conditions are described for the preparation of 1,3-dienes by vinylstannane homocoupling using palladium(II)-catalysis with oxygen (or air) for Pd(0)/Pd(II) reoxidation; related homo-couplings, and cross-coupling reactions with allylstannane, are used to obtain 1,3-diynes, biaryls and 1,4-dienes.

Stereoselective synthesis of (Z,E)-2-phenylselenobutadienes by palladium-catalyzed cross-coupling reaction

Hydrozirconation of 1-alkynes gives ( E )-alkenylzirconium complexes 3, which are cross-coupled with (E)-α-phenylselenovinyl bromides (4) in the presence of tetrakis (triphenylphosphine) palladium catalyst to afford (Z,E )-2-phenylselenobutadienes (5) in good yields.

Photoisomerization of cis,cis-1,4-diphenyl-1,3-butadiene in glassy media at 77 K: The bicycle-pedal mechanism

The cis-trans photoisomerization of cis,cis-1,4-diphenyl-1,3-butadiene in a soft isopentane glass at 77 K gives significant two-bond photoisomerization in contrast to solution and hard glassy media where only one-bond photoisomerization takes place. The Royal Society of Chemistry 2006.

Hydrocupration of Alkynes: a Simple Synthesis of (E,E)-1,3-Dienes

Copper(I) hydride species, prepared in situ in tetrahydrofuran using NaBH4-MgBr2-Et3N-CuCl or NaH-MgBr2-CuCl reagent systems, convert terminal alkynes into (E,E)-1,3-dienes in good yields.

Mechanisms of photoisomerization of polyenes in confined media: From organic glasses to protein binding cavities

Photochemical reactivities of model organic systems (stilbene and diphenylbutadiene) in organic glasses were first examined and compared with those in solution and in organized media. These observations were in turn compared with reactivities of polyene chromophores in protein binding cavities (specifically PYP, rhodopsin and bacteriorhodopsin). The obvious conclusion is that the preference for the most volume-conserving Hula-twist mechanism isomerization in organic glasses is because of the close interaction between the guest and the host molecules. In organized media (zeolites, crystals and protein binding cavities), the residual empty space coupled with any specific guest-host interactions that are characteristic of a given system, could lead to involvement of the more volume-demanding one-bond-flip (i.e. torsional relaxation) or bicycle-pedal or an extended HT process in photoisomerization.

New aspects of diphenylbutadiene photochemistry. Regiospecific Hula-twist photoisomerization

In EPA glass at liquid nitrogen temperature, the E,E isomer of diphenylbutadiene (DPB) was photostable, while both the Z,E and Z,Z isomers underwent selective HT isomerization at center 1 giving the stable conformer of the double-bond isomerized trans product. That HT-1 was involved rather than the OBF process was shown by results of o,o-dimethyl-DPB. Formation of unstable trans product corresponded to simultaneous configurational and conformational isomerization. The regioselectivity was found not sensitive to a substituent effect, as shown by the similar reactivity in p,p- or o,o-bistrifluoromethyl-DPB. Copyright

Direct and Sensitized Photoisomerization of 1,4-Diphenylbutadienes

Photoisomerization of the three stereoisomers of 1,4-diphenylbutadiene (DPB) in room-temperature cyclohexane solution was studied by direct excitation and by triplet sensitization.The photostationary mixtures in both singlet and triplet experiments contain only trans,trans and cis,trans isomers; no cis,cis isomer or any photoproducts were observed.The two cis isomers exhibit no measureable fluorescence or triplet formation. results are interpreted in terms of allylmethylene-like intermediates.Efficient internal conversion of singlet DPBs is inferred from low isomerization quantum yields by direct excitation.Triplet-sensitized isomerizations show a marked DPB concentration dependence of photostationary compositions and quantum yields.Analysis of these data reveals a quantum chain process involving excited triplet DPB as the chain-carrying species.Transient absorption measurements show that sensitized excitation of any DPB isomer leads directly to a fast equilibrium between triplet all-trans and trans-twisted forms.