53783-59-8

Basic information

• Product Name: Benzeneethanol, b-ethylidene-, (E)-
• CAS NO: 53783-59-8
• Molecular Formula: C10H12O
• Molecular Weight: 148.205
• Mol File: 53783-59-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzeneethanol, b-ethylidene-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneethanol, b-ethylidene-, (E)-(53783-59-8)
• EPA Substance Registry System: Benzeneethanol, b-ethylidene-, (E)-(53783-59-8)

Safety Data

• Hazardous Substances Data: 53783-59-8(Hazardous Substances Data)

Upstream product

• 591-50-4 iodobenzene 
• 673-32-5 1-Phenylprop-1-yne 
• 50-00-0 formaldehyd 
• 122-78-1 phenylacetaldehyde 
• 4411-89-6 2-phenyl-2-butenal 
• 764-01-2 methyl propargyl alcohol 
• 108-86-1 bromobenzene 
• 504-61-0 (E)-but-2-enol 

Downstream Products

• 87585-80-6 (E)-2-Phenyl-2-butenyl tosylate 
• 1301701-44-9 (E)-2-phenylbut-2-enyl 2-(2,2,2-trifluoroacetamido)acetate 
• 343335-93-3 E-1-Brom-2-phenylbuten-⁽²⁾ 
• 1612240-13-7 (E)-1-chloro-3-((2-phenylbut-2-en-1-yl)oxy)benzene 
• 1612240-35-3 (E)-5-((2-phenylbut-2-en-1-yl)oxy)bicyclo[4.2.0]octa-1,3,5-trien-7-ol 
• 1612240-42-2 (E)-5-((2-phenylbut-2-en-1-yl)oxy)bicyclo[4.2.0]octa-1,3,5-trien-7-one 
• 87567-35-9 1-(Neophylsulfonyl)-3-phenyl-(Z)-pent-3-ene 

Relevant articles and documents

Divergent regioselectivity in the synthesis of trisubstituted allylic alcohols by nickel- and ruthenium-catalyzed alkyne hydrohydroxymethylation with formaldehyde

Stoichiometric metals banned: Nonsymmetrically disubstituted alkynes were converted into primary trisubstituted allylic alcohols upon exposure to paraformaldehyde in the presence of nickel or ruthenium catalysts, which exhibit complementary regioselectivity and complete stereoselectivity in the absence of exogenous reducing agents (see scheme). Copyright

Arylation of allyl alcohols in organic and aqueous media catalyzed by oxime-derived palladacycles: Synthesis of β-arylated carbonyl compounds

A 4-hydroxyacetophenone oxime-derived palladacycle catalyzes the Mizoroki-Heck reaction of allyl alcohols with aryl iodides, bromides, and chlorides in aqueous and organic solvents. The reaction takes place in the presence of dicyclohexylmethylamine or cesium carbonate as bases, the addition of tetrabutylammonium bromide (TBAB) as additive for aryl bromides and chlorides being necessary. Under these reaction conditions, β-arylated aldehydes and ketones are mainly obtained using a rather low loading of palladium (0.1-1 mol%). Similar catalytic activity is shown by a Kaiser oxime resin-derived palladacycle, which allows one to perform recycling and reusing experiments with low Pd leaching. The high regio- and chemoselectivity observed supported that these palladacycles, working as a source of Pd(0) species, operates mainly through a neutral mechanism. This methodology has been applied to the synthesis of important β-arylated carbonyl compounds, such as 4-phenylbutan-2-one, 4-(4-hydroxyphenyl)butan-2-one, dihydrochalcones, the anti-inflamatory nabumetone, and the fragance β-lilial. γ-Arylation is observed in the reactions of allyl alcohol and but-3-en-2-ol with 2-iodoaniline giving mainly the corresponding quinolines. The same tendency is observed in the case of 1,1-dimethylallyl alcohol affording either γ-arylated alcohols or (E)-1-arylisoprenes.

Stille coupling versus cine substitution. Electronic effects also influence coupling sterically hindered stannanes

Very low ligand to palladium ratios, especially weak ligands and iodides as electrophiles allow Stille couplings to very hindered stannanes, not possible under common conditions. In contrast, the usage of triflates and elevated temperatures yields exclusi