87212-87-1

Basic information

• Product Name: (1Z,3Z)-1,4-di-p-tolylbuta-1,3-diene
• Synonyms: (1Z,3Z)-1,4-di-p-tolylbuta-1,3-diene
• CAS NO: 87212-87-1
• Molecular Weight: 234.341
• Mol File: 87212-87-1.mol

Chemical Properties

• CAS DataBase Reference: (1Z,3Z)-1,4-di-p-tolylbuta-1,3-diene(CAS DataBase Reference)
• NIST Chemistry Reference: (1Z,3Z)-1,4-di-p-tolylbuta-1,3-diene(87212-87-1)
• EPA Substance Registry System: (1Z,3Z)-1,4-di-p-tolylbuta-1,3-diene(87212-87-1)

Safety Data

• Hazardous Substances Data: 87212-87-1(Hazardous Substances Data)

Upstream product

• 104-82-5 4-Methylbenzyl chloride 
• 1504-75-2 3-(4-methylphenyl)acrylaldehyde 
• 18869-29-9 (E)-4,4'-dimethylstilbene 
• 75-20-7 calcium carbide 
• 189331-74-6 (Z)-4,4‘-(but-1-en-3-yne-1,4-diyl)bis(methylbenzene) 
• 52916-86-6 2,3-dibromo-3-p-tolyl-propionic acid 
• 1866-39-3 trans-p-methylcinnamic acid 
• 73839-44-8 (Z)-1-[2-bromovinyl]-4-methylbenzene 
• 110296-03-2 (Z)-(4-methylstyryl)(phenyl)telluride 
• 121758-59-6 (Z,Z)-bis(p-metylstyryl) telluride 
• 201230-82-2 carbon monoxide 
• 60655-80-3 (E)-4-methylstyrenyl bromide 
• 644-97-3 Dichlorophenylphosphine 
• 766-97-2 4-n-methylphenylacetylene 

Downstream Products

• 123559-76-2 4,7-Bis-(4-chloro-phenyl)-3a,4,7,7a-tetrahydro-isobenzofuran-1,3-dione 
• 123559-77-3 3,6-Bis-(4-chloro-phenyl)-cyclohex-4-ene-1,2-dicarboxylic acid 
• 1287736-93-9 2-phenyl-3,5-di-p-tolylpyridine 
• 66365-87-5 1,2,5-tri-p-tolyl-1H-phosphole 1-oxide 
• 222158-85-2 (3aS,7aR)-4,7-Di-p-tolyl-3a,7a-dihydro-isobenzofuran-1,3-dione 

Relevant articles and documents

Efficient Z-Selective Semihydrogenation of Internal Alkynes Catalyzed by Cationic Iron(II) Hydride Complexes

The bench-stable cationic bis(σ-B-H) aminoborane complex [Fe(PNPNMe-iPr)(H)(η2-H2B = NMe2)]+ (2) efficiently catalyzes the semihydrogenation of internal alkynes, 1,3-diynes and 1,3-enynes. Moreover, selective incorporation of deuterium was achieved in the case of 1,3-diynes and 1,3-enynes. The catalytic reaction takes place under mild conditions (25 °C, 4-5 bar H2 or D2) in 1 h, and alkenes were obtained with high Z-selectivity for a broad scope of substrates. Mechanistic insight into the catalytic reaction, explaining also the stereo- and chemoselectivity, is provided by means of DFT calculations. Intermediates featuring a bisdihydrogen moiety [Fe(PNPNMe-iPr)(η2-H2)2]+ are found to play a key role. Experimental support for such species was unequivocally provided by the fact that [Fe(PNPNMe-iPr)(H)(η2-H2)2]+ (3) exhibited the same catalytic activity as 2. The novel cationic bisdihydrogen complex 3 was obtained by protonolysis of [Fe(PNPNMe-iPr)(H)(η2-AlH4)]2 (1) with an excess of nonafluoro-tert-butyl alcohol.

Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step

The gold(I)-catalyzed reaction of acetylene gas with alkenes leads to (Z,Z)-1,4-disubstituted 1,3-butadienes and biscyclopropanes depending on the donor ligand on gold(I). Acetylene was generated in situ from calcium carbide and water in a user-friendly p

Effect of substituents and conjugated chain length on the UV spectra of α,ω-di-substituted phenyl polyenes

A series of α,ω-di-substituted phenyl polyenes, p-X-Ph(CH = CH)nPh-p-Y (n = 1, 2, or 3) were synthesized, and their ultraviolet (UV) absorption maximum wavelength were determined. The correlation between molecular structure and the maximum wavelength energy (wavenumber/cm -1) was carried out. The results show that the maximum wavelength energy of the title compounds is mainly affected by both substituent excited-state parameters and maximum wavelength energy of the parent molecule. However, the two influence factors are not independent, and the action of substituent is governed by the parent molecular absorption energy. In the case of the compounds containing NO2 or NH2 groups, the influence of interaction of polarity parameters on the maximum wavelength energy must also be considered. In addition, the exploration was also made for the quantifying correlation of UV absorption maximum wavelength energy with the conjugated polarizability potential CPP replacing the parent molecular absorption energy. And the results indicate that the equation with CPP parameters is more accurate and convenient. Copyright 2013 John Wiley & Sons, Ltd. For the α,ω-di-substituted phenyl polyenes, p-X-Ph(CH = CH)nPh-p-Y (n = 1, 2, or 3), their ultraviolet absorption maximum wavelength energy (wavenumber/cm-1) was mainly affected by both substituent excited-state parameters and maximum wavelength energy of the parent molecule. However, the two influence factors are not independent, and the action of substituent is governed by the parent molecular absorption energy. Copyright

Reactivity differences between 2,4- and 2,5-disubstituted zirconacyclopentadienes: A highly selective and general approach to 2,4-disubstituted phospholes

Mixtures of 2,4- and 2,5-disubstituted zirconacyclopentadienes were obtained by the reductive dimerisation of terminal alkynes using the Cp 2ZrCl2/lanthanum system. Reactions of dihalophosphines with these mixtures afforded selectively the corresponding 2,4-disubstituted phospholes and 1,4-disubstituted butadienes. A new series of phospholes was characterized by multi-nuclear NMR spectroscopy and X-ray analysis. A possible explanation for the observed selectivity was obtained from X-ray studies and DFT analysis of the intermediate zirconacyclopentadienes. The Royal Society of Chemistry 2013.

Iron-catalysed, hydride-mediated reductive cross-coupling of vinyl halides and Grignard reagents

An iron-catalysed, hydride-mediated reductive cross-coupling reaction has been developed for the preparation of alkanes. Using a bench-stable iron(ii) pre-catalyst, reductive cross-coupling of vinyl iodides, bromides and chlorides with aryl- and alkyl Grignard reagents successfully gave the products of formal sp3-sp3 cross-coupling reactions.

Palladium-catalyzed oxidative homocoupling of potassium alkenyltrifluoroborates: synthesis of symmetrical 1,3-dienes

Herein, we describe a convenient method for the synthesis of symmetrical 1,3-dienes employing an oxidative palladium-catalyzed homocoupling of potassium alkenyltrifluoroborates providing products in good yields relative to existing methodologies. This is the first report of a cross-dimerization of potassium alkenyltrifluoroborates.

Palladium-catalyzed homocoupling reactions of organic tellurides

Organic tellurides containing a styryl moiety react in acetonitrile to give the corresponding homocoupling products, 1,3-dienes, with moderate to quantitative yields in the presence of a catalytic amount of Pd(OAc)2 together with AgOAc at 25 °C. In contrast, such homocoupling reactions hardly occur with diaryl, alkyl aryl, dialkyl, and alkynyl aryl tellurides, even at reflux temperature and in the presence of a stoichiometric amount of palladium salt, in disagreement with reported results. The result of cross-over experiments suggests that this homocoupling reaction occurs between an alkenyl telluride and an alkenylpalladium species, the latter being formed via the migration of an alkenyl moiety from Te to Pd (transmetallation).

REDUCTIVE DIMERIZATION OF VINYL HALIDES IN AN Ni/Pb/Al THREE METAL REDOX SYSTEM. A FACILE ACCESS TO TERPHENYL DERIVATIVES

A novel three metal redox system, NiCl2(bpy)/PbBr2/Al, is found to be potent in the reductive coupling of vinyl halides, affording 1,4-biaryl-1,3-butadienes, precursors of terphenyl derivatives.

A CONVENIENT METHOD FOR THE CONVERSION OF trans to cis-CINNAMIC ACIDS

trans-Cinnamic acids react in sequence with bromine, base, and carbon monoxide to give cis-acids in reasonable yields.