863098-32-2

Basic information

• Product Name: 1-(4-(bromoethynyl)phenyl)-ethan-1-one
• Synonyms: 1-(4-(bromoethynyl)phenyl)-ethan-1-one
• CAS NO: 863098-32-2
• Molecular Weight: 223.069
• Mol File: 863098-32-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-(4-(bromoethynyl)phenyl)-ethan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-(bromoethynyl)phenyl)-ethan-1-one(863098-32-2)
• EPA Substance Registry System: 1-(4-(bromoethynyl)phenyl)-ethan-1-one(863098-32-2)

Safety Data

• Hazardous Substances Data: 863098-32-2(Hazardous Substances Data)

Upstream product

• 42472-69-5 4-ethynylacetophenone 
• 99-90-1 para-bromoacetophenone 
• 75883-03-3 4'-(2-trimethylsilylethynyl)acetophenone 

Downstream Products

• 123770-66-1 1-{4-[2-(4-methylphenyl)ethynyl]phenyl}ethanone 

Relevant articles and documents

Nickel-Catalyzed Reductive 1,2-Dialkynylation of Alkenes Bearing an 8-Aminoquinoline Directing Group

An unprecedented nickel-catalyzed reductive 1,2-dialkynylation of alkenes bearing an 8-aminoquinoline directing group has been developed. This method proceeded through a migratory insertion/reductive-coupling process under mild conditions with a wide substrate scope and good functional group tolerance, providing direct access to the synthetically flexible 1,5-diynes. Moreover, the 1,2-dialkynylation products could be further converted to borate-ester- or azide-functionalized 1,5-dienes, ditriazole, β-diyne primary amide, and trisubstituted benzene.

Palladium end-capped polyynes via oxidative addition of 1-haloalkynes to Pd(PPh3)4

Reported here is the use of 1-haloacetylenes and 1-halopolyynes as synthons for the preparation of new palladium(II) end-capped polyynes. The 1-haloalkynes were obtained in a series of transformations from para-substituted bromoarenes that included Sonogashira coupling followed by halogenation and chain elongation via Cadiot-Chodkiewicz protocol. The key step for the synthesis of metal complexes was oxidative addition of 1-haloalkynes to Pd(PPh3)4, which allowed obtaining a series of metal compounds 1-5-CnX with carbon chains up to hexatriyne in 75-100% yield. All the compounds were characterized by NMR and HRMS or elemental analysis. The 13C spectra of the 1-haloalkynes showed interesting, although expected, shifts of the carbon chain atoms close to the halogen termini. X-ray crystal structures were obtained for three polyynes-two butadiynes (2-C4[Pd]Br and 3-C4[Pd]Br) and one hexatriyne (1-C6[Pd]Br)-and the latter is the first reported X-ray crystal structure of palladium end-capped hexatriyne.

Protection/deprotection-free syntheses and structural analysis of (keto-aryl)diynes

The reactions of precursors 4-BrC6H4COR with TMSC≡CH (Sonogashira coupling) followed by in situ deprotection and subsequent dimerization gave thermally stable dimeric ketodiynes RCOC 6H4(C≡C)2C6