109027-84-1

Basic information

• Product Name: 1-bromo-4-(pent-1-yn-1-yl)benzene
• Synonyms: 1-bromo-4-(pent-1-yn-1-yl)benzene
• CAS NO: 109027-84-1
• Molecular Weight: 223.112
• Mol File: 109027-84-1.mol

Chemical Properties

• CAS DataBase Reference: 1-bromo-4-(pent-1-yn-1-yl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-bromo-4-(pent-1-yn-1-yl)benzene(109027-84-1)
• EPA Substance Registry System: 1-bromo-4-(pent-1-yn-1-yl)benzene(109027-84-1)

Safety Data

• Hazardous Substances Data: 109027-84-1(Hazardous Substances Data)

Upstream product

• 627-19-0 1-Pentyne 
• 589-87-7 1,4-bromoiodobenzene 
• 60-29-7 diethyl ether 
• 3375-31-3 palladium diacetate 

Downstream Products

• 1352441-06-5 trimethyl((4-(pent-1-ynyl)phenyl)ethynyl)silane 
• 175283-28-0 1-iodo-4-(pent-1-ynyl)benzene 
• 1416339-64-4 1-(4-bromophenyl)-2-propylnaphthalene 
• 136618-02-5 Acetic acid (4-pent-1-ynyl-phenyl)-(5-trimethylsilanyl-furan-3-yl)-methyl ester 
• 120755-54-6 Acetic acid (2-hydroxy-5-oxo-2,5-dihydro-furan-3-yl)-(4-pent-1-ynyl-phenyl)-methyl ester 

Relevant articles and documents

Post-functionalization of disubstituted polyacetylenes via click chemistry

We report a synthetic design and the experimental exploration of preparation of disubstituted polyacetylenes (PAs, P3) through 1,3-dipolar cycloaddition of azides with precursor PA bearing alkyne pendants. The precursor PA (P2) was derived by desilylation of the pristine PA with trimethylethynylsilane side chains (P1). P1 was obtained by polymerization of a dual-alkyne containing monomer with one of the alkynes end-capping by trimethylsilane (M) under the promotion of WCl6-Ph4Sn catalyst. Two synthetic routes, i.e. two-steps (from P1 to P3 via precursor P2) and one-pot (from P1 to P3 without separation and purification of P2) were tried and the results indicated that one-pot strategy is more facile and resultant P3-1 showed higher purity and higher molecular weight than the resultant of P3-2. By using the techniques such as GPC, FTIR and 1H NMR spectroscopy the polymerization behavior and the structures of the polymers were well characterized.

Gold(I)-Catalyzed Haloalkynylation of Aryl Alkynes: Two Pathways, One Goal

Haloalkynylation reactions provide an efficient method for the simultaneous introduction of a halogen atom and an acetylenic unit. For the first time, we report a gold(I)-catalyzed haloalkynylation of aryl alkynes that delivers exclusively the cis addition product. This method enables the simple synthesis of conjugated and halogenated enynes in yields of up to 90 %. Notably, quantum chemical calculations reveal an exceptional interplay between the place of the attack at the chloroacetylene: No matter which C?C bond is formed, the same enyne product is always formed. This is only possible through rearrangement of the corresponding skeleton. Hereby, one reaction pathway proceeds via a chloronium ion with a subsequent aryl shift; in the second case the corresponding vinyl cation is stabilized by a 1,3-chlorine shift. 13C-labeling experiments confirmed that the reaction proceeds through both reaction pathways.

Regio- and Stereoselective Cyanotriflation of Alkynes Using Aryl(cyano)iodonium Triflates

A novel, mild, and versatile approach for regioselective syn-addition of both the CN and OTf groups of aryl(cyano)iodonium triflates to alkynes is described. The reaction uses Fe-catalysis and can be conducted in gram scale. Products of the vicinal cyanotriflation can be stereospecifically readily further functionalized, rendering the method highly valuable.

Anti-inflammatory furanones

New 5-hydroxy-2-furanone compounds having anti-inflammatory, immunosuppressive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis.