77295-59-1

Basic information

• Product Name: Benzene, 1-chloro-4-(2,2-dibromoethenyl)-
• CAS NO: 77295-59-1
• Molecular Formula: C8H5Br2Cl
• Molecular Weight: 296.389
• Mol File: 77295-59-1.mol
• Article Data: 61

Chemical Properties

• CAS DataBase Reference: Benzene, 1-chloro-4-(2,2-dibromoethenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-chloro-4-(2,2-dibromoethenyl)-(77295-59-1)
• EPA Substance Registry System: Benzene, 1-chloro-4-(2,2-dibromoethenyl)-(77295-59-1)

Safety Data

• Hazardous Substances Data: 77295-59-1(Hazardous Substances Data)

Upstream product

• 622-95-7 4-chlorobenzyl bromide 
• 104-88-1 4-chlorobenzaldehyde 
• 558-13-4 carbon tetrabromide 
• 52372-80-2 4-Chlorobenzaldehyde monohydrazone 
• 52372-80-2 (4-chlorobenzylidene)hydrazine 
• 81559-60-6 1-Chloro-4-(2,2,2-tribromo-ethyl)-benzene 
• 603-35-0 triphenylphosphine 

Downstream Products

• 66482-30-2 (Z)-1-bromo-2-(4-chlorophenyl)ethylene 
• 66482-29-9 1-[(E)-2-bromoethenyl]-4-chlorobenzene 
• 39672-21-4 1-(4-methoxyphenyl)-2-(4-chlorophenyl)acetylene 
• 78704-49-1 1-(4-chlorophenyl)-2-trimethylsilylacetylene 
• 3240-10-6 (4-chlorophenyl)propiolic acid 
• 1160723-52-3 N-benzyl-N-((4-chlorophenyl)ethynyl)-4-methylbenzenesulfonamide 
• 101554-06-7 2-(4-chlorobenzyl)benzo[d]oxazole 
• 1374348-10-3 2-((4-chlorophenyl)ethynyl)-5-phenyl-1,3,4-oxadiazole 
• 1391467-36-9 C₁₂H₁₁BrClNO 
• 1391467-49-4 C₁₂H₁₁BrClNO 
• 1426841-23-7 4-(4-chlorophenyl)-2,2-dimethylbut-3-ynenitrile 
• 1426841-39-5 4-(4-chlorophenyl)-2-ethyl-2-methylbut-3-ynenitrile 
• 1426841-40-8 1-((4-chlorophenyl)ethynyl)cyclohexanecarbonitrile 
• 28446-72-2 (2E)-3-(4-chlorophenyl)acrylonitrile 

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.

Synthesis of Chiral Propargylamines, Chiral 1,2-Dihydronaphtho[2,1-b]furans and Naphtho[2,1-b]furans with C-Alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals and β-Naphthols

Chiral phosphoric acid-catalyzed couplings of C-alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals with β-naphthols led to chiral propargylamines in moderate to high yields with high to excellent enantioselectivity, in which the reactions underwent sequential chiral phosphoric acid-catalyzed in situ formation of N-(tert-butoxycarbonyl)-imines (N-Boc-imines) from the aminals, and 1,2-addition of β-naphthols to the N-Boc-imines. Chiral 1,2-dihydronaphtho[2,1-b]furans and naphtho[2,1-b]furans were prepared with satisfactory results when 10 mol% AgOAc and 20 mol% 2,6-lutidine or 1.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were added to the resulting chiral propargylamines solution, respectively.

A Radical-Initiated Fragmentary Rearrangement Cascade of Ene-Ynamides to [1,2]-Annulated Indoles via Site-Selective Cyclization

Straightforward access to [1,2]-annulated indoles, key substructures in natural products, is highly desirable yet challenging. Herein, a radical triggered fragmentary cyclization cascade reaction of ene-ynamides is presented, providing a rapid access into [1,2]-annulated indoles by an intermolecular radical addition, intramolecular cyclization, desulfonylative aryl migration, and site-selective C(sp2)-N cyclization sequence. DFT calculations support oxidation of N-centered radical species to cations prior to the C-N bond formation, followed by an unusual aza-Nazarov cyclization.