74568-53-9

Basic information

• Product Name: methyl 3-bromo-4-hydroxycinnamate
• Synonyms: methyl 3-bromo-4-hydroxycinnamate
• CAS NO: 74568-53-9
• Molecular Weight: 257.084
• Mol File: 74568-53-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl 3-bromo-4-hydroxycinnamate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-bromo-4-hydroxycinnamate(74568-53-9)
• EPA Substance Registry System: methyl 3-bromo-4-hydroxycinnamate(74568-53-9)

Safety Data

• Hazardous Substances Data: 74568-53-9(Hazardous Substances Data)

Upstream product

• 2973-78-6 3-bromo-4-hydroxybenzylaldehyde 
• 6329-78-8 N-(3-bromo-4-hydroxyphenyl)acetamide 
• 292638-85-8 acrylic acid methyl ester 
• 5927-18-4 trimethyl phosphonoacetate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 73747-61-2 (3-bromo-4-hydroxy-benzylidene)-malonic acid 
• 186581-53-3 diazomethane 
• 119405-32-2 3-bromo-4-hydroxy cinnamic acid 
• 1252036-60-4 3-bromo-4-hydroxybenzenediazonium tetrafluoroborate 

Downstream Products

• 140-67-0 Estragole 
• 74568-54-0 trans-2-bromo-4-(3-hydroxypropen-1-yl)phenol 
• 104-46-1 anethole 
• 74568-55-1 (E)-3-[3-Bromo-4-(3-chloro-2-hydroxy-propoxy)-phenyl]-propenol 
• 51765-07-2 (E)-3-[3-Bromo-4-(2-hydroxy-3-isopropylamino-propoxy)-phenyl]-propenol 
• 51765-08-3 1-[trans-2-bromo-4-(3-hydroxyprop-1-enyl)phenoxy]-3-(tert-butylamino)-2-propanol 
• 77587-14-5 (E)-3-(3-Bromo-4-methoxymethoxy-phenyl)-acrylic acid methyl ester 

Relevant articles and documents

A deacetylation-diazotation-coupling sequence: Palladium-catalyzed C-C bond formation with acetanilides as formal leaving groups

Acetanilides can be deacetylated and diazotized in situ, and subsequently used in Pd-catalyzed coupling reactions without isolation of the diazonium intermediate. Heck reactions, Suzuki crosscoupling reactions, and a Pd-catalyzed [2+2+1] cycloaddition hav

Mizoroki-heck reactions with 4-phenoldiazonium salts

Significantly better yields were achieved in Mizoroki-Heck reactions using 4-phenoldiazonium salts instead of their O-alkylated analogues under otherwise identical conditions. We found that a one-flask deacetylation-diazotation- precipitation sequence starting from paracetamol or acetanilides derived thereof provides a convenient access to the required diazonium tetrafluoroborates. The utility of these arylating agents in palladium-catalyzed C-C bond forming reactions was demonstrated for a one-flask-synthesis of the heterocyclic core of the drug aripiprazole. Notably, the diazonium salt formation from an acetanilide could be combined with two Pd-catalyzed steps in a one-flask sequence, without any exchange of solvents or isolation of intermediates.