74684-45-0

Basic information

• Product Name: (E)-1-Anisyl-2-(p-nitrophenyl)propen-1-yl chloride
• Synonyms: (E)-1-Anisyl-2-(p-nitrophenyl)propen-1-yl chloride
• CAS NO: 74684-45-0
• Molecular Weight: 303.745
• Mol File: 74684-45-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-1-Anisyl-2-(p-nitrophenyl)propen-1-yl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-Anisyl-2-(p-nitrophenyl)propen-1-yl chloride(74684-45-0)
• EPA Substance Registry System: (E)-1-Anisyl-2-(p-nitrophenyl)propen-1-yl chloride(74684-45-0)

Safety Data

• Hazardous Substances Data: 74684-45-0(Hazardous Substances Data)

Upstream product

• 10486-08-5 sodium p-thiocresolate 
• 74684-46-1 (Z)-1-Anisyl-2-(p-nitrophenyl)propen-1-yl chloride 
• 54166-35-7 NaSph-4-Cme₃ 
• 74684-48-3 1-(p-Methoxyphenyl)-1,1,2-trichloro-2-(p-nitrophenyl)-propane 

Downstream Products

• 74684-47-2 1-(p-Methoxyphenyl)-2-(p-nitrophenyl)-1-propanone 
• 74684-49-4 (E)-1-(p-Methoxyphenyl)-2-(p-nitrophenyl)propen-1-yl ethyl ether 
• 74684-50-7 (Z)-1-(p-Methoxyphenyl)-2-(p-nitrophenyl)propen-1-yl ethyl ether 
• 100-19-6 (4-nitrophenyl)ethanone 
• 74684-52-9 (Z)-1-(p-Methoxyphenyl)-2-(p-nitrophenyl)-propen-1-yl trifluoroethyl ether 
• 74684-51-8 (E)-1-(p-Methoxyphenyl)-2-(p-nitrophenyl)-propen-1-yl trifluoroethyl ether 
• 103-19-5 di(p-tolyl) disulfide 
• 74684-46-1 (Z)-1-Anisyl-2-(p-nitrophenyl)propen-1-yl chloride 
• 74684-53-0 (E)-1-(p-Methoxyphenyl)-2-(p-nitrophenyl)-propen-1-yl p-toluenethiolate 
• 74684-54-1 (Z)-1-(p-Methoxyphenyl)-2-(p-nitrophenyl)-propen-1-yl p-toluenethiolate 
• 7605-48-3 bis(4-tert-butylphenyl)disulfide 
• 74684-56-3 (Z)-1-(p-Methoxyphenyl)-2-(p-nitrophenyl)-propen-1-yl p-tert-butylbenzenethiolate 
• 74684-55-2 (E)-1-(p-Methoxyphenyl)-2-(p-nitrophenyl)-propen-1-yl p-tert-butylbenzenethiolate 

Relevant articles and documents

Vinylic Cations from Solvolysis. 33. Solvolysis of (E)- and (Z)-1-Anisyl-2-(p-nitrophenyl)propen-1-yl chlorides

The solvolysis of (E)- and (Z)-1-anisyl-2-p-nitrophenylpropen-1-yl chlorides (4-E and 4-Z) in buffered aqueous EtOH, TFE, and aqueous TFE was studied.The products in aqueous EtOH are a 6:4 ratio of the ethers 9-E and 9-Z and 1-anisyl-2-(p-nitrophenyl)-1-propanone (6), and in TFE a 7:3 ratio of the trifluoroethyl ethers 11-E and 11-Z and 6 are formed. The Grunwald-Winstein m values at 120 deg C in aqueous EtOH are 0.53 (4-E) and 0.62 (4-Z) and in aqueous TFE are 0.98 (4-E) and 0.88 (4-Z).In aqueous EtOH, common-ion rate depression and a 4-E 4-Z isomerization during the solvolysis are negligible, whereas in TFE and less so in aqueous TFE strong common-ion rate depression and an extensive isomerization, which give an equilibrium ratio of 66:34 4-E/4-Z, accompany the solvolysis.In 80percent EtOH/p-MeC6H4S(1-) the reaction is of second order, the products are a 6:4 ratio of the vinyl thiolates 12-E and 12-Z, and a rapid 4-E 4-Z isomerization takes place.In TFE containing CF3CH2O(1-) or p-MeC6H4S(1-) neither isomerization nor common-ion rate depression were observed, and the reactions were several times faster than in TFE/2,6-luitidine.An ionization to a cationoid species is suggested in all cases except in 80percent EtOH/RS(1-).In aqueous EtOH the reaction probably proceeds via the ion pairs 24a and 24b, whose capture by the solvent is slower than their interconversion but faster than internal return. In TFE a long-lived and selective free vinyl cation, 23, is formed. Preferential capture of the Cl(1-) over the solvent occurs from the less hindered side of 23, resulting in common-ion rate depression and isomerization. In the presence of the stronger nucleophiles RO(1-) and RS(1-), the capture occurs at the ion-pair stage. In 80percent EtOH/p-MeC6H4S(1-) the mechanism is probably a nucleophilic substitution via a carbanionic intermediate, but the isomerization follows a different route, probably a reversible electron-transfer process.