39491-55-9

Basic information

• Product Name: Benzene, 1,3-pentadienyl-, (Z,E)-
• CAS NO: 39491-55-9
• Molecular Formula: C11H12
• Molecular Weight: 144.216
• Mol File: 39491-55-9.mol
• Article Data: 36

Chemical Properties

• CAS DataBase Reference: Benzene, 1,3-pentadienyl-, (Z,E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,3-pentadienyl-, (Z,E)-(39491-55-9)
• EPA Substance Registry System: Benzene, 1,3-pentadienyl-, (Z,E)-(39491-55-9)

Safety Data

• Hazardous Substances Data: 39491-55-9(Hazardous Substances Data)

Upstream product

• 34862-94-7 (E)-1-phenyl-1-penten-3-ol 
• 1401009-09-3 C₁₅H₂₃O₃PS 
• 67-56-1 methanol 
• 76620-26-3 sodium salt of (Z)-1-phenyl-3-penten-1-one N-tosylhydrazone 
• 1608-27-1 ((1E)-penta-1,3-dien-1-yl)benzene 
• 76620-26-3 sodium salt of (E)-1-phenyl-3-penten-1-one N-tosylhydrazone 
• 41892-64-2 (but-2-enylidene)triphenyl-λ⁵-phosphane 
• 100-52-7 benzaldehyde 
• 13291-18-4 isopropenylmagnesium bromide 
• 370867-96-2 (+/-)-(E)-2-[2-(diphenylphosphanyl)benzoyloxy]-1-phenyl-3-pentene 
• 110-44-1 sorbic Acid 
• 591-50-4 iodobenzene 
• 14371-10-9 (E)-3-phenylpropenal 
• 1530-32-1 ethyltriphenylphosphonium bromide 

Downstream Products

• 3909-96-4 (1E,3E)-1-phenyl-1,3-pentadiene 
• 1608-27-1 (Z)-1-phenyl-4-methyl-1,3-butadiene 
• 39491-56-0 (Z)-penta-1,3-dienylbenzene 
• 1236889-51-2 C₁₈H₂₀O 

Relevant articles and documents

Ni-Catalyzed Regioselective Hydroarylation of 1-Aryl-1,3-Butadienes with Aryl Halides

An efficient nickel-catalyzed regioselective hydroarylation of 1,3-dienes with aryl halides and a silane has been developed, affording a range of allylic arenes in good to excellent yields under mild conditions. This method exhibits broad substrate scope,

Palladium-Catalyzed Regio- A nd Enantioselective Hydrosulfonylation of 1,3-Dienes with Sulfinic Acids: Scope, Mechanism, and Origin of Selectivity

Chiral sulfones are important structural motifs in organic synthesis because of their widespread use in pharmaceutical chemistry. In particular, chiral allylic sulfones have drawn particular interest because of their synthetic utility. However, enantioselective synthesis of 1,3-disubstituted unsymmetrical chiral allylic sulfones remains a challenge. In this article, we report a protocol for (R)-DTBM-Segphos/Pd-catalyzed regio- A nd enantioselective hydrosulfonylation of 1,3-dienes with sulfinic acids, which provides atom- A nd step-economical access to 1,3-disubstituted chiral allylic sulfones. The reaction occurs under mild conditions and has a broad substrate scope. Combined experimental and computational studies suggest that the reaction is initiated by a ligand-to-ligand hydrogen transfer followed by a C-S bond reductive elimination via a six-membered transition state. Steric repulsion between the olefinic C-H of the substrate and the tert-butyl group of (R)-DTBM-Segphos was found to be a key factor in the enantiocontrol.

Transition-Metal-Free Allylic Borylation of 1,3-Dienes

This work explains the reactivity of diboron reagents with 1,3-dienes in a transition-metal-free context. The sole addition of Na2CO3 (30 mol %) to bis(pinacolato)diboron in MeOH allows the 1,4-hydroboration of cyclic and noncyclic 1,3-dienes. The electronic influence on the substrate guarantees the conjugated 1,4-hydroboration versus 1,2-diboration. DFT calculations show that the distribution of charge in the allylic anion intermediate governs the selectivity toward 1,4-hydroboration, while the favored trans configuration in diene reagents determines the preference for the E allyl boronate products.