5738-43-2

Basic information

• Product Name: Anthracene, 9-[(1E)-3-phenyl-1-propenyl]-
• CAS NO: 5738-43-2
• Molecular Formula: C23H18
• Molecular Weight: 294.396
• Mol File: 5738-43-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Anthracene, 9-[(1E)-3-phenyl-1-propenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Anthracene, 9-[(1E)-3-phenyl-1-propenyl]-(5738-43-2)
• EPA Substance Registry System: Anthracene, 9-[(1E)-3-phenyl-1-propenyl]-(5738-43-2)

Safety Data

• Hazardous Substances Data: 5738-43-2(Hazardous Substances Data)

Upstream product

• 83152-05-0 trans-3-(9-anthryl)-1-phenylpropene 
• 300-57-2 allylbenzene 
• 1564-64-3 9-Bromoanthracene 
• 103-63-9 1-phenyl-2-bromoethane 
• 642-31-9 9-anthracene aldehyde 
• 83135-57-3 cis-1-(9-anthryl)-3-phenylpropene 
• 50688-75-0 1-(9-anthryl)-3-phenyl-1-propanol 

Downstream Products

• 83135-57-3 cis-1-(9-anthryl)-3-phenylpropene 
• 83152-05-0 trans-3-(9-anthryl)-1-phenylpropene 
• 74387-95-4 1-(9-Anthryl)-3-(phenyl)propane 

Relevant articles and documents

Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols

Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols provides chalcones and benzyl styrenes. The use of various metal triflates is investigated herein for facile and efficient redox transformation. A plausible mechanism has been proposed.

Double-Bond-Stabilizing Abilities of 1-Methyl-2-pyrrolyl, 9-Anthryl, and o-Tolyl Substituents

Equilibrium constants have been determined for the isomerisations of trans-PhCH=CHCH2X to trans-PhCH2CH=CHX, where X is 1-methyl-2-pyrrolyl, 9-anthryl, and o-tolyl.The values (estimated standard deviations) at 30 deg C in tert-butyl alcohol are 1.53 (0.04), 0.342 (0.022), and 0.407 (0.011), respectively.The equilibrium constant for the 9-anthryl case is only about two-thirds as large as a value reported previously.Steric factors are believed to be the most important reason 9-anthryl and o-tolyl groups are poorer double-bond-stabilizing substituents than phenyl groups.Resonance effects are probably decisive in making 1-methyl-2-pyrrolyl substituents better than phenyl but not as good as 2-furyl at stabilizing double bonds.The organolithium compounds formed in the reaction of butyllithium with either trans-1-(9-anthryl)-3-phenylpropene (7) or trans-3-(9-anthryl)-1-phenylpropene (8) react with water to give about 11percent 7, 27percent 8, and 58percent of what appears to be 9-(3-phenyl-2-propenylidene)-9,10-dihydroanthracene.Similar quenching of organolithium compounds in the o-tolyl case gave approximately the equilibrium mixture and in the 1-methyl-2-pyrrolyl case gave almost equal amounts of cis-1-(1-methyl-2-pyrrolyl)-3-phenylpropene (37percent), trans-1-(1-methyl-2-pyrrolyl)-3-phenylpropene (33percent), and trans-3-(1-methyl-2-pyrrolyl)-1-phenylpropene (30percent).The equilibrium constant for the trans-to-cis isomerization of PhCH2CH=CHX at 25 deg C is 0.164 (0.011) when X is 1-methyl-2-pyrrolyl, 0.801 (0.027) when X is 9-anthryl, and 0.039 (0.011) when X is o-tolyl. trans-1-(2-Pyrrolyl)-3-(dimethylamino)propene was prepared but could not be isomerized in the presence of potassium tert-butoxide, probably because of anion formation at the pyrrole NH position.In tert-butyl alcohol-dimethyl sulfoxide containing potassium tert-butoxide, trans-1-(1-methyl-2-pyrrolyl)-3-(dimethylamino)propene appeared to isomerize to trans-3-(1-methyl-2-pyrrolyl)-1-(dimethylamino)propene with an equilibrium constant of 21 (5), but the evidence for this is incomplete.