37904-42-0

Basic information

• Product Name: Benzene, (5-methyl-3,5-hexadienyl)-, (E)-
• CAS NO: 37904-42-0
• Molecular Formula: C13H16
• Molecular Weight: 172.27
• Mol File: 37904-42-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzene, (5-methyl-3,5-hexadienyl)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, (5-methyl-3,5-hexadienyl)-, (E)-(37904-42-0)
• EPA Substance Registry System: Benzene, (5-methyl-3,5-hexadienyl)-, (E)-(37904-42-0)

Safety Data

• Hazardous Substances Data: 37904-42-0(Hazardous Substances Data)

Upstream product

• 557-93-7 2-bromoprop-1-ene 
• 62692-41-5 (E)-(4-bromobut-3-en-1-yl) benzene 
• 104-53-0 3-phenyl-propionaldehyde 
• 6415-11-8 (E)-hex-3-en-5-yn-1-ylbenzene 
• 33046-41-2 (E)-6-phenyl-3-hexen-2-one 
• 75-16-1 methylmagnesium bromide 
• 221543-20-0 Phosphoric acid (E)-1-methylene-5-phenyl-pent-2-enyl ester diphenyl ester 
• 122894-93-3 (E)-2-Methyl-6-phenyl-hex-3-en-2-ol 
• 114444-86-9 Acetate((E)-3,7-dimethyl-octa-2,6-dienyl)-triphenyl-phosphonium; 
• 4303-59-7 2-methylallyltriphenylphosphonium chloride 
• 1530-49-0 methallyltributylphosphonium chloride 

Relevant articles and documents

Nickel-catalyzed reductive 1,3-diene formation from the cross-coupling of vinyl bromides

Facile construction of 1,3-dienes building upon cross-electrophile coupling of two open-chain vinyl halides is disclosed in this work, showing moderate chemoselectivities between the terminal bromoalkenes and internal vinyl bromides. The present method is mild and tolerates a range of functional groups and can be applied to the total synthesis of a tobacco fragrance solanone.

Olefination with Sulfonyl Halides and Esters: E-Selective Synthesis of Alkenes from Semistabilized Carbanion Precursors

Carbanions of sulfonyl halides and activated sulfonates add to carbonyl compounds, and so-formed aldol-type adducts spontaneously fragment into olefins. This transformation mimics the one-pot Julia olefination with (hetero)aryl sulfones, but the mechanism of fragmentation involves a four-membered intermediate, typical for reactivity of phosphorus reagents. Moreover, in contrast to the reactions of sulfones, sulfonates of fluorinated alcohols (TFE and HFI) produce byproducts that are easily removed during workup. In our report, we focus on reactions of unstabilized and semistabilized carbanion precursors: alkylsulfonates, and allyl- and benzylsulfonates, respectively. In particular for semistabilized systems, olefins were synthesized as predominant E isomers in good yields. The presented studies reveal that optimal reaction conditions, including the type of base and alcohol groups of the sulfonates, are different depending on stabilization of the carbanion precursors and structure of the carbonyl substrates. The practical synthetic guide is supplemented with a discussion of the mechanism, based on reactivity studies of intermediates and identification of side-products.

Nickel-catalyzed cross-coupling of dienyl phosphates with Grignard reagents in the synthesis of 2-substituted 1,3-dienes

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