153136-77-7

Basic information

• Product Name: (E)-ethyl 3-(2-hydroxy-5-nitrophenyl)acrylate
• Synonyms: (E)-ethyl 3-(2-hydroxy-5-nitrophenyl)acrylate
• CAS NO: 153136-77-7
• Molecular Weight: 237.212
• Mol File: 153136-77-7.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (E)-ethyl 3-(2-hydroxy-5-nitrophenyl)acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-ethyl 3-(2-hydroxy-5-nitrophenyl)acrylate(153136-77-7)
• EPA Substance Registry System: (E)-ethyl 3-(2-hydroxy-5-nitrophenyl)acrylate(153136-77-7)

Safety Data

• Hazardous Substances Data: 153136-77-7(Hazardous Substances Data)

Upstream product

• 97-51-8 5-Nitrosalicylaldehyde 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 105-36-2 ethyl bromoacetate 
• 100-02-7 4-nitro-phenol 
• 140-88-5 ethyl acrylate 
• 105-39-5 chloroacetic acid ethyl ester 
• 2725-81-7 6-nitrocoumarin 
• 141-52-6 sodium ethanolate 

Downstream Products

• 146767-12-6 ethyl 3-(5-amino-2-hydroxyphenyl)propionate 
• 1357381-89-5 6-nitro-4-phenyl-2H-chromen-2-one 
• 197707-72-5 ethyl-3-{5-[4-(dimethylaminocarbonyl)butanoylamino]-2-hydroxyphenyl}propanoate 
• 197726-37-7 ethyl-3-{5-[4-(dimethylaminocarbonyl)butanoylamino]-2-[9-(4-methoxyphenyl)-7-oxo-5E-nonenyloxy]phenyl}propanoate 
• 197726-35-5 ethyl-3-{5-[4-(dimethylaminocarbonyl)butanoylamino]-2-(7-oxo-5E-pentadecenyloxy)phenyl}propanoate 
• 197726-36-6 ethyl-3-{2-(7-cyclohexyl-7-oxo-5E-heptenyloxy)-5-[4-(dimethylaminocarbonyl)butanoylamino]phenyl}propanoate 
• 197726-33-3 ethyl-3-{5-[4-(dimethylaminocarbonyl)butanoylamino]-2-(4-formylbutoxy)phenyl}propanoate 
• 197725-73-8 ethyl-3-{5-[4-(dimethylaminocarbonyl)butanoylamino]-2-(5-hydroxypentoxy)phenyl}propanoate 

Relevant articles and documents

Visible-Light-Induced C(sp2)-C(sp3) Coupling Reaction for the Regioselective Synthesis of 3-Functionalized Coumarins

A photocatalysis strategy for the regioselective synthesis of 3-functionalized coumarins is reported. With visible light irradiation, a direct and regioselective C(sp2)-C(sp3) coupling reaction of 3-(2-hydroxyphenyl)acrylates with ethers or thioethers occurs by using Ru(bpy)3Cl2·6H2O as a photocatalyst and TBHP as an oxidant. The cascade process involves alkenylation of the C(sp3)-H bond of ethers and lactonization, furnishing 3-alkylated coumarins as the final products. This approach is characterized by a broad substrate scope, mild reaction conditions, and simplified operation. The synthesis of 3-alkylated coumarins could be realized by a one-pot procedure, starting from commercially available salicylaldehyde.

Cascade Synthesis of 4-Arylcoumarins: Pd-Catalyzed Arylations and Cyclizations with (E)-Ethyl 3-(2-Hydroxyaryl)acrylates and Triarylantimony Difluorides

Herein, we describe a simple general method for the synthesis of 4-arylcoumarins using pentavalent organoantimony compounds. The reactions of 3-(2-hydroxyaryl)acrylates with triarylantimony difluorides in the presence of Pd(OAc)2 (10 mol-%) and 2,2'-bipyridyl (10 mol-%) at 80 °C under aerobic conditions afforded 4-arylcoumarins in good-to-excellent yields. This protocol involves a cascade oxidative Heck-type arylation followed by cyclization, with all the aryl groups in the triarylantimony difluoride transferred to the coupling products. Triarylantimony difluorides resulted in better outcomes than those obtained with other pentavalent organoantimony or bismuth compounds.

3-Trifluoromethylated Coumarins and Carbostyrils by Radical Trifluoromethylation of ortho-Functionalized Cinnamic Esters

A method for the trifluoromethylation of ortho-hydroxycinnamic esters was developed to achieve the regioselective synthesis of 3-trifluoromethylated coumarins. The reaction was performed by using the Togni reagent as the CF3source under mild conditions and showed good functional- group tolerance. The scope of this copper-mediated method was further expanded to the synthesis of 3-trifluoromethylated carbostyrils starting from ortho-aminocinnamic derivatives. Interestingly, a sequential one-pot synthesis of 3-trifluoromethylated coumarins starting from salicylaldehydes was further developed. The mechanism of this cascade reaction was explored, and a radical pathway was found to be consistent with the obtained results.