253684-21-8

Basic information

• Product Name: methyl 4-(2,2-dibromovinyl)benzoate
• Synonyms: methyl 4-(2,2-dibromovinyl)benzoate
• CAS NO: 253684-21-8
• Molecular Formula: C₁₀H₈Br₂O₂
• Molecular Weight: 320
• Mol File: 253684-21-8.mol
• Article Data: 22

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: methyl 4-(2,2-dibromovinyl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-(2,2-dibromovinyl)benzoate(253684-21-8)
• EPA Substance Registry System: methyl 4-(2,2-dibromovinyl)benzoate(253684-21-8)

Safety Data

• Hazardous Substances Data: 253684-21-8(Hazardous Substances Data)

Upstream product

• 558-13-4 carbon tetrabromide 
• 1571-08-0 methyl 4-formylbenzoate 

Downstream Products

• 42497-80-3 methyl 4-(phenylethynyl)benzoate 
• 253684-52-5 methyl (Z)-4-(2-bromo-2-phenylvinyl)benzoate 
• 229174-44-1 methyl 4-[(2-methoxyphenyl)ethynyl]benzoate 

Relevant articles and documents

Expedient Synthesis of Bridged Bicyclic Nitrogen Scaffolds via Orthogonal Tandem Catalysis

Bridged nitrogen bicyclic skeletons have been accessed via unprecedented site- and diastereoselective orthogonal tandem catalysis from readily accessible reactants in a step economic manner. Directed Pd-catalyzed γ-C(sp3)-H olefination of aminocyclohexane with gem-dibromoalkenes, followed by a consecutive intramolecular Cu-catalyzed amidation of the 1-bromo-1-alkenylated product delivers the interesting normorphan skeleton. The tandem protocol can be applied on substituted aminocyclohexanes and aminoheterocycles, easily providing access to the corresponding substituted, aza- and oxa-analogues. The Cu catalyst of the Ullmann-Goldberg reaction additionally avoids off-cycle Pd catalyst scavenging by alkenylated reaction product. The picolinamide directing group stabilizes the enamine of the 7-alkylidenenormorphan, allowing further product post functionalizations. Without Cu catalyst, regio- and diastereoselective Pd-catalyzed γ-C(sp3)-H olefination is achieved.

Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand

The hydroformylation of terminal arylalkynes and enynes offers a straightforward synthetic route to the valuable (poly)enals. However, the hydroformylation of terminal alkynes has remained a long-standing challenge. Herein, an efficient and selective Rh-catalyzed hydroformylation of terminal arylalkynes and conjugated enynes has been achieved by using a new stable biphosphoramidite ligand with strong π-acceptor capacity, which affords various important E-(poly)enals in good yields with excellent chemo- and regioselectivity at low temperatures and low syngas pressures.

Pd-Catalyzed Indole Synthesis via C-H Activation and Bisamination Sequence with Diaziridinone

This work describes an efficient Pd-catalyzed indole synthesis. A wide variety of indoles can be obtained in good yields from readily available vinyl bromides. The reaction likely proceeds through a sequential aryl C-H activation and bisamination of a resulting pallada(II)cycle with diaziridinone.