169694-34-2

Basic information

• Product Name: Benzene, (3-methyl-1,5-hexadienyl)-
• CAS NO: 169694-34-2
• Molecular Formula: C13H16
• Molecular Weight: 172.27
• Mol File: 169694-34-2.mol

Chemical Properties

• CAS DataBase Reference: Benzene, (3-methyl-1,5-hexadienyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, (3-methyl-1,5-hexadienyl)-(169694-34-2)
• EPA Substance Registry System: Benzene, (3-methyl-1,5-hexadienyl)-(169694-34-2)

Safety Data

• Hazardous Substances Data: 169694-34-2(Hazardous Substances Data)

Upstream product

• 17488-65-2 4-phenylbut-3-en-2-ol 
• 762-72-1 allyl-trimethyl-silane 
• 52755-38-1 1-phenyl-2-buten-1-ol 
• 52755-39-2 (2E)-1-phenylbut-2-en-1-ol 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 53317-08-1 9-allyl-9-bora-bicyclo[3.3.1]nonane 
• 24808-74-0 (+/-)-3-methoxy-1-phenyl-1-butene 

Relevant articles and documents

Rhenium complex-catalyzed carbon-carbon formation of alcohols and organosilicon compounds

The coupling reactions of allylic and benzylic alcohols and allyltrimethylsilane are efficiently catalyzed by a rhenium complex to give the corresponding 1,5-dienes and alkenes in moderate to good yields. Similarly, alcohols were coupled with ketene silyl acetals to form the corresponding esters.

High-yielding and rapid carbon-carbon bond formation from alcohols: Allylation by means of TiCl4

TiCl4 efficiently promotes high yield (80-99%) replacement of OH in tertiary, benzylic, and allylic alcohols, and even nonactivated secondary alcohols, by an allyl group. The reaction usually proceeds within minutes at room temperature. Georg Thieme Verlag Stuttgart. New York.

Fluorinated alcohols as promoters for the metal-free direct substitution reaction of allylic alcohols with nitrogenated, silylated, and carbon nucleophiles

The direct allylic substitution reaction using allylic alcohols in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and 2,2,2-trifluoroethanol (TFE) as reaction media is described. The developed procedure is simple, works under mild conditions (rt, 50 and 70 °C), and proves to be very general, since different nitrogenated nucleophiles and carbon nucleophiles can be used achieving high yields, especially when HFIP is employed as solvent and aromatic allylic alcohols are the substrates. Thus, sulfonamides, carbamates, carboxamides, and amines can be successfully employed as nitrogen-based nucleophiles. Likewise, silylated nucleophiles such as trimethylsilylazide, allyltrimethylsilane, trimethylsilane, and trimethylsilylphenylacetylene give the corresponding allylic substitution products in high yields. Good results for the Friedel-Crafts adducts are also achieved with aromatic compounds (phenol, anisole, indole, and anilines) as nucleophiles. Particularly interesting are the results obtained with electron-rich anilines, which can behave as nitrogenated or carbon nucleophiles depending on their electronic properties and the solvent employed. In addition, 1,3-dicarbonyl compounds (acetylacetone and Meldrum's acid) are also successfully employed as soft carbon nucleophiles. Studies for mechanism elucidation are also reported, pointing toward the existence of carbocationic intermediates and two working reaction pathways for the obtention of the allylic substitution product.

"Design" of boron-based compounds as pro-nucleophiles and co-catalysts for indium(I)-catalyzed allyl transfer to various Csp 3-type electrophiles

We have recently uncovered a general indium(I)-catalyzed method for allylations and propargylation of acetals and ketals with a water- and air-stable allyl boronate. By using a more reactive allyl borane, we have successfully extended this methodology to the more challenging C-C coupling with ethers. Herein, we report an improved methodology for the indium(I)-catalyzed allylation of acetals and ethers, through combination of the allyl boronate with a commercially available "hard" Lewis acid, B-methoxy-9-BBN (BBN=borabicyclo[3.3.1]nonane), as an effective co-catalyst. Significantly, our work highlights for the first time the correlation between the Lewis acidity of "electrophilic" boron-based compounds and their " nucleophilic" reactivity in Csp3-Csp3 couplings, catalyzed by a "soft" low-oxidation main group metal. In addition, we also report several applications of these methodologies to the selective synthesis of various carbohydrate derivatives. Copyright

Indium(i)-catalyzed alkyl-allyl coupling between ethers and an allylborane

An efficient method for alkyl-allyl cross-coupling between ethers and a 9-BBN-derived allylborane catalyzed by indium(i) triflate has been developed. The allylborane proved to be essential to obtain the desired products in high yields. The reaction displayed good substrate scope including high functional group tolerance. The Royal Society of Chemistry 2011.

Direct allylation of α-aryl alcohols with allyltrimethylsilane catalyzed by heterogeneous tin ion-exchanged montmorillonite

The direct allylation of α-aryl alcohols with allyltrimethylsilane efficiently proceeded in the presence of tin ion-exchanged montmorillonite under mild conditions according to the proper addition order of reactants and a catalyst.