5808-05-9

Basic information

• Product Name: Benzene, 1,1'-(1,3-butadiene-1,4-diyl)bis-, (E,Z)-
• CAS NO: 5808-05-9
• Molecular Formula: C16H14
• Molecular Weight: 206.287
• Mol File: 5808-05-9.mol
• Article Data: 63

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-(1,3-butadiene-1,4-diyl)bis-, (E,Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-(1,3-butadiene-1,4-diyl)bis-, (E,Z)-(5808-05-9)
• EPA Substance Registry System: Benzene, 1,1'-(1,3-butadiene-1,4-diyl)bis-, (E,Z)-(5808-05-9)

Safety Data

• Hazardous Substances Data: 5808-05-9(Hazardous Substances Data)

Upstream product

• 105654-27-1 (Z,Z)-bis(2-phenylethenyl)telluride 
• 536-74-3 phenylacetylene 
• 4440-01-1 lithium phenylacetylide 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 588-73-8 (Z)-β-bromostyrene 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 14371-10-9 (E)-3-phenylpropenal 
• 4706-43-8 1-benzyl-1H-benzotriazole 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 7436-90-0 2,2-dibromostyrene 
• 100-52-7 benzaldehyde 
• 63520-74-1 C₈H₇ClMg 
• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 139926-43-5 (E,E)-bis(2-phenylethenyl)telluride 

Downstream Products

• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 1347759-87-8 cis-N-p-toluenesulfonyl-2,5-diphenyl-3-pyrroline 
• 538-81-8 C₁₆H₁₄ 

Relevant articles and documents

Ruthenium-catalysed oxidative coupling of vinyl derivatives and application in tandem hydrogenation

The first ruthenium-catalyzed oxidative homo- and cross-coupling of exclusive vinyl derivatives giving highly valued 1,3-diene building blocks is reported. The catalytic system is based on readily available reagents and it mainly delivers the E,E isomer. This methodology also enables the synthesis of adipic acid ester derivatives in a one-pot fashion after in situ ruthenium-catalyzed hydrogenation.

Carbon-carbon bond forming reactions via Pd-catalyzed detellurative homocoupling of diorganyl tellurides

A simple and highly efficient method for the constructions of Csp-Csp, Csp2-Csp2 and Csp3-Csp3 bonds is reported. The symmetrical diaryl tellurides undergo detellurative homocouplings to afford symmetrical biaryl products. The reactions are carried out at ambient temperature using PdCl2 as a catalyst in the presence of Ag2O and Na2CO3. Similarly, the detellurative homocouplings of dibenzyl telluride and bis(phenylethynyl)telluride give bibenzyl and the conjugated diyne, respectively.

Catalytic Dehydrogenative C-C Coupling by a Pincer-Ligated Iridium Complex

The pincer-iridium fragment (iPrPCP)Ir (RPCP = ?3-2,6-C6H3(CH2PR2)2) has been found to catalyze the dehydrogenative coupling of vinyl arenes to afford predominantly (E,E)-1,4-diaryl-1,3-butadienes. The eliminated hydrogen can undergo addition to another molecule of vinyl arene, resulting in an overall disproportionation reaction with 1 equiv of ethyl arene formed for each equivalent of diarylbutadiene produced. Alternatively, sacrificial hydrogen acceptors (e.g., tert-butylethylene) can be added to the solution for this purpose. Diarylbutadienes are isolated in moderate to good yields, up to ca. 90% based on the disproportionation reaction. The results of DFT calculations and experiments with substituted styrenes indicate that the coupling proceeds via double C-H addition of a styrene molecule, at β-vinyl and ortho-aryl positions, to give an iridium(III) metalloindene intermediate; this intermediate then adds a β-vinyl C-H bond of a second styrene molecule before reductively eliminating product. Several metalloindene complexes have been isolated and crystallographically characterized. In accord with the proposed mechanism, substitution at the ortho-aryl positions of the styrene precludes dehydrogenative homocoupling. In the case of 2,4,6-trimethylstyrene, dehydrogenative coupling of β-vinyl and ortho-methyl C-H bonds affords dimethylindene, demonstrating that the dehydrogenative coupling is not limited to C(sp2)-H bonds.