61153-37-5

Basic information

• Product Name: Benzene, 1-(1E)-1-hexenyl-4-methyl-
• CAS NO: 61153-37-5
• Molecular Formula: C13H18
• Molecular Weight: 174.286
• Mol File: 61153-37-5.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1-(1E)-1-hexenyl-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-(1E)-1-hexenyl-4-methyl-(61153-37-5)
• EPA Substance Registry System: Benzene, 1-(1E)-1-hexenyl-4-methyl-(61153-37-5)

Safety Data

• Hazardous Substances Data: 61153-37-5(Hazardous Substances Data)

Upstream product

• 106-38-7 para-bromotoluene 
• 29541-98-8 pentylidenetriphenylphosphorane 
• 104-87-0 4-methyl-benzaldehyde 
• 109-72-8 n-butyllithium 
• 592-41-6 1-hexene 
• 71-41-0 pentan-1-ol 
• 56949-84-9 1-(1Z)-1-hexen-1-yl-4-methylbenzene 
• 37617-02-0 1-methoxy-1-hexene 
• 380481-66-3 5,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborinane 
• 156423-16-4 (E)-1-(2-iodovinyl)-4-methylbenzene 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 60655-80-3 (E)-4-methylstyrenyl bromide 
• 1116-70-7 tri(n-butyl)aluminium 
• 624-31-7 4-tolyl iodide 

Relevant articles and documents

Highly E-Selective, Stereoconvergent Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Alkenyl Ethers

An improved method for the nickel-catalyzed Suzuki-Miyaura cross-coupling of alkenyl ethers is reported. This stereoconvergent protocol allows for the utilization of a wide range of alkenyl ethers and aryl boronic esters for the synthesis of variously sub

1-Methyl-1H-tetrazol-5-yl (MT) sulfones in the Julia-Kocienski olefination: Comparison with the PT and the TBT sulfones

The stability and the stereoselectivity of newly prepared n-pentyl 1-methyl-1H-tetrazol-5-yl (MT) sulfone 1a in the Julia-Kocienski reactions were compared with those of the PT sulfone 1b and the TBT sulfone 1c. The improved stability of the anion derived from the n-pentyl MT sulfone 1a enhanced the efficiency of the olefination reactions and gave higher yields of the product alkenes 3 compared with the PT sulfone 1b. Especially high E-selectivity and high yields were obtained from the reaction with aromatic aldehydes and α,β-unsaturated aldehydes. The selectivity of 1a was not so sensitive to the change of base counter ion compared with the PT sulfone 1b. The reaction of the MT sulfones having either ethyl or a longer alkyl chain also gave E-alkenes selectively in high yields.

Stereospecific Iron-Catalyzed Carbon(sp2)-Carbon(sp3) Cross-Coupling with Alkyllithium and Alkenyl Iodides

An efficient synthetic protocol involving iron-catalyzed cross-coupling reactions between organolithium compounds and alkenyl iodides as key coupling partners was achieved. More than 30 examples were obtained with moderate to good yields and high stereospecificity. Gram-scale and synthetic applications of this procedure are recorded herein to demonstrate its feasibility and potential utilization.

Metal-Catalyzed Remote Functionalization of ω-Ene Unsaturated Ethers: Towards Functionalized Vinyl Species

The combined ruthenium-catalyzed chain walking with the nickel-catalyzed cross-coupling reaction of ω-alkenyl ethers provide a unique entry to functionalized vinyl species. This transformation illustrates the power and flexibility of remote functionalization by demonstrating the compatibility of two independent reactions involving unrelated sites.

General copper-catalyzed coupling of alkyl-, aryl-, and alkynylaluminum reagents with organohalides

We report the first example of a very general Cu-catalyzed cross-coupling of organoaluminum reagents with organohalides. The reactions proceed for the couplings of alkyl-, aryl-, and alkynylaluminum reagents with aryl and heteroaryl halides and vinyl bromides, affording the cross-coupled products in good to excellent yields. Both primary and secondary alkylaluminum reagents can be utilized as organometallic coupling partners. These reactions are not complicated by β-hydride elimination, and as a result rearranged products are not observed with secondary alkylaluminum reagents even for couplings with heteroaryl halides under "ligand-free" conditions. Radical clock experiment with a radical probe and relative reactivity study of Ph3Al with two haloarenes, 1-bromonaphthalene and 4-chlorobenzonitrile, having two different redox potentials indicates that the reaction does not involve free aryl radicals and radical anions as intermediates. These results combined with the result of the Hammett plot obtained by reacting Ph3Al with iodoarenes containing p-H, p-Me, p-F, and p-CF3 substituents, which shows a linear curve (R2 = 0.99) with a ρ value of +1.06, suggest that the current transformation follows an oxidative addition-reductive elimination pathway.

Catalytic activity of Pd(II) and Pd(II)/DAB-R systems for the Heck arylation of olefins

Palladium-catalyzed reactions of aryl bromides with various olefins involving Pd(II)/diazabutadiene (DAB-R) systems have been investigated. The scope of a coupling process using Pd(II) sources and an α-diimine as ligand in the presence of Cs2CO3 as base was tested using various substrates. The Pd(OAc)2/ DAB-Cy (1, DAB-Cy=1,4-dicyclohexyl-diazabutadiene) system presents the highest activity with respect to electron-neutral and electron-deficient aryl bromides in coupling with electron rich olefins. The synthesis and X-ray characterization of a Pd(II)-diazabutadiene ligand is reported. Extensive optimization experiments showed that another Pd(II) source, Pd(acac)2 (acac=acetylacetonate), proved to activate aryl bromides at high temperatures, low catalyst loadings when the appropriate concentration of nBu4NBr additive was employed. The effect of the DAB-Cy ligand is important at very low catalyst loadings and high temperatures. Pd(acac)2 and Pd(acac)2 /DAB-Cy precatalysts were very effective for the arylation of various olefins with aryl bromides with respect to reaction rate, catalyst loadings, and functional group tolerance.

An amphiphilic resin-supported palladium catalyst for high-throughput cross-coupling in water

(figure presented) The Suzuki-Miyaura coupling of aryl halides (8 varieties) and aryl-or vinylboronic acids (12 varieties) took place in water in the presence of a palladium complex of an amphiphilic polystyrene-poly(ethylene glycol) copolymer resin-supported N-anchored 2-aza-1,3-bis(diphenylphosphino)-propane ligand and potassium carbonate to give uniform and quantitative yields of the corresponding biaryls (96 varieties).

Platinum-catalyzed cross-couplings of organoboronic acids with aryl iodides

Tetrakis(triphenylphosphine)platinum in DMF was utilized as a mild catalyst for cross coupling reactions of organoboronic acids with aryl iodides. The present reactions exhibited excellent group-selectivity where couplings of organoboronic acids 2a-e with 4-bromo-1-iodobenzene (4) give 4-arylbromobenzenes 5a-b and 4-alkenylbromobenzenes 5c-e in excellent yields.

Highly selective coupling of organoboron compounds via oxovanadium(v)-induced oxidation

Reaction of organoboranes or organoborane ate complexes (obtained by treatment with BunLi or CsF) with oxovanadium(v) compounds results in the intramolecular oxidative coupling of organic groups on the boranes or borates.

Palladium-catalyzed cross-coupling of organozirconium compounds with diaryliodonium salts

The palladium-catalyzed cross-coupling reaction of diaryliodonium salts with organozirconium compounds was achieved for about 1-1.5 hrs at room temperature and the reaction proceeded with retention of configuration to provide a new convenient method for the synthesis of (E)-disubstituted alkenes.