190649-11-7

Basic information

• Product Name: Benzene, 1-bromo-4-(1-hexynyl)-
• Synonyms: 1-bromo-4-(hex-1-ynyl)benzene;4-bromo-1-(1-hexyl)benzene;Benzene,1-bromo-4-(1-hexynyl);1-(4-bromophenyl)hex-1-yne
• CAS NO: 190649-11-7
• Molecular Formula: C12H13Br
• Molecular Weight: 237.139
• Mol File: 190649-11-7.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: Benzene, 1-bromo-4-(1-hexynyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-bromo-4-(1-hexynyl)-(190649-11-7)
• EPA Substance Registry System: Benzene, 1-bromo-4-(1-hexynyl)-(190649-11-7)

Safety Data

• Hazardous Substances Data: 190649-11-7(Hazardous Substances Data)

Upstream product

• 589-87-7 1,4-bromoiodobenzene 
• 693-02-7 hex-1-yne 
• 133381-92-7 hexynylzinc bromide 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 75618-25-6 butyl triflate 
• 5467-74-3 4-Bromophenylboronic acid 
• 42930-39-2 n-butylzinc chloride 

Downstream Products

• 1644664-75-4 methyl (2E,4E)-4-(4-bromobenzylidene)oct-2-enoate 
• 1385029-71-9 (S)-methyl 2-(4-bromophenyl)-3-butyl-1-phenylcycloprop-2-enecarboxylate 
• 1379681-00-1 C₁₈H₂₆BBrO₂ 
• 1379681-15-8 C₁₈H₂₆BBrO₂ 

Relevant articles and documents

In Situ Generation of Alkynylzinc and Its Subsequent Negishi Reaction in a Flow Reactor

A highly efficient and convenient Negishi cross-coupling reaction has been developed for the synthesis of unsymmetrical alkynes and enynes in a continuous-flow process. The reaction proceeds through an in situ generated alkynylzinc reagent by the reaction of lithium acetylide with zinc halide at room temperature followed by a cross-coupling reaction with aryl or vinyl iodides. The notable features of this work compared to the conventional benchtop method are mild reaction conditions, good to excellent yields, broad functional-group compatibility, short residence time (73 sec) and especially desilylation of TMS group with the residence time of only 10.5 sec.

Alkylation of Terminal Alkynes under Zinc Lewis Acid Catalysis and Its Mechanistic Studies

With a zinc Lewis acid catalyst and proton sponge in toluene, terminal alkynes were found to undergo the alkylation by alkyl triflates to provide unsymmetrical internal alkynes. This is the first example that a simple alkyl chain other than benzylic and norbornyl units can be introduced onto the alkynyl carbon atom under Lewis acid catalysis. Mechanistic studies revealed that the activation of the alkyne by the zinc Lewis acid and proton sponge is the trigger of the reaction to give a monoalkynylzinc species, which successively reacts with the alkyl triflate to afford the internal alkyne. A radical pathway is unlikely in this system. (Figure presented.).

Splitting a Substrate into Three Parts: Gold-Catalyzed Nitrogenation of Alkynes by C-C and C≡C Bond Cleavage

A gold-catalyzed nitrogenation of alkynes for the synthesis of carbamides and amino tetrazoles through C-C and C≡C bond cleavages is described. A diverse set of functionalized carbamide and amino tetrazole derivatives were selectively constructed under mild conditions. The chemoselectivity can be easily switched by the selection of the acid additives. The reaction is characterized by its broad substrate scope, direct construction of high value products, easy operation under air, and mild conditions at room temperature. This chemistry provides a way to transform alkynes by splitting the substrate into three parts.