766-96-1

Usage

Uses

Used in the Synthesis of Advanced Materials:
4-Bromophenylacetylene is used as a starting material for the development of second-order nonlinear optical materials. These materials exhibit the ability to manipulate light at the molecular level, which is crucial for applications in optoelectronics, photonics, and advanced communication technologies.
Used in the Formation of Heterocyclotriynes:
4-Bromophenylacetylene is also utilized in the synthesis of heterocyclotriynes, which are valuable intermediates in organic chemistry. Heterocyclotriynes are known for their ability to form stable complexes with transition metals, making them useful in the creation of novel coordination compounds and catalysts.
Used in the Production of Unsymmetrical 1,4-Diarylbutadiynes:
4-Bromophenylacetylene serves as a key component in the preparation of unsymmetrical 1,4-diarylbutadiynes. These organic molecules are of interest in materials science due to their potential use in the development of new polymers and organic semiconductors.
Used in Organic Synthesis:
In the specific case of 1-bromo-4-(4′-tetrahydropyranyloxy-1′-ethynylphenyl)benzene synthesis, 1-Bromo-4-ethynylbenzene is used as a precursor. 4-Bromophenylacetylene is an example of how 4-Bromophenylacetylene can be employed in the synthesis of complex organic molecules for various applications, including pharmaceuticals and specialty chemicals.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 3224, 1989 DOI: 10.1021/jo00274a055Tetrahedron, 62, p. 6673, 2006 DOI: 10.1016/j.tet.2005.12.077

InChI:InChI=1/C8H5Br/c1-2-7-3-5-8(9)6-4-7/h1,3-6H

Upstream product

• 99-90-1 para-bromoacetophenone 
• 58229-01-9 1-Bromo-4-(2,2-dichloro-1-fluoro-vinyl)-benzene 
• 217469-81-3 ((4-bromophenyl)ethynyl)triethylsilane 
• 37828-68-5 1,1-dichloro-1-(4'-bromophenyl)ethane 
• 14063-78-6 3-(4-bromophenyl)-3-chloroprop-2-enal 
• 67-56-1 methanol 
• 16116-78-2 (4-bromophenyl)(trimethylsilyl)acetylene 
• 589-87-7 1,4-bromoiodobenzene 
• 4301-14-8 acetylenemagnesium bromide 
• 14235-81-5 4-Ethynylaniline 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 1122-91-4 4-bromo-benzaldehyde 
• 106-37-6 1.4-dibromobenzene 
• 2039-82-9 1-bromo-4-ethenyl-benzene 

Downstream Products

• 14063-78-6 3-(4-bromophenyl)-3-chloroprop-2-enal 
• 59673-48-2 4-(3-(4-bromophenyl)prop-2-yn-1-yl)morpholine 
• 16116-78-2 (4-bromophenyl)(trimethylsilyl)acetylene 
• 143647-59-0 3-(p-bromophenylethynyl)-2,3-dihydro-3-hydroxy-2-phenyl-1H-isoindol-1-one 
• 107433-65-8 methyl 5-hydroxy-7-<4-(1-hydroxynonyl)phenyl>hept-6-ynoate 
• 107433-64-7 1-(4-ethynylphenyl)nonan-1-ol 
• 129837-42-9 4-(bromostyryl)(methyl)sulfane 
• 133383-82-1 1-Bromo-4-[bromo-(2,2,5,5-tetramethyl-cyclopentylidene)-methyl]-benzene 
• 99337-18-5 2-(4-bromophenyl)-3-(trimethylsilyl)-(Z)-prop-2-enenitrile 
• 99337-19-6 2-(4-cyanophenyl)-3-(trimethylsilyl)-(Z)-prop-2-enenitrile 
• 82721-75-3 (E)-(1-(4-bromophenyl)-2-tosylprop-1-en-1-yl)(phenyl)selane 
• 3246-80-8 9-phenyl-9H-xanthene 
• 136482-74-1 C₈H₄BrK 
• 71955-86-7 6-bromo-3-chlorobenzotellurophene 

Relevant academic research and scientific papers

BIPHENYL COMPOUNDS AS SOCE MODULATORS, COMPOSITIONS AND USES THEREOF

Compound of formula (I) able to modulate Store Operated Calcium Entry (SOCE). The disclosure also relates to compositions and uses of compounds of formula (I) for treatment of disease condition depending on increased/ decreased activity of SOCE.

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.

Decarboxylation-triggered homo-Nazarov cyclization of cyclic enol carbonates catalyzed by rhenium complex

Decarboxylative homo-Nazarov cyclization catalyzed by a Lewis acid was achieved using a cyclic enol carbonate bearing a cyclopropane moiety as a substrate. Various substrates were converted into the corresponding multi-substituted cyclohexenones in good yieldsviadecarboxylation, followed by 6-membered ring formation involving cyclopropane-ring-opening.

Synthesis and Photochemical Application of Hydrofluoroolefin (HFO) Based Fluoroalkyl Building Block

A novel fluoroalkyl iodide was synthesized on multigram scale from refrigerant gas HFO-1234yf as cheap industrial starting material in a simple, solvent-free, and easily scalable process. We demonstrated its applicability in a metal-free photocatalytic ATRA reaction to synthesize valuable fluoroalkylated vinyl iodides and proved the straightforward transformability of the products in cross-coupling chemistry to obtain conjugated systems.

Synthesis of alkynes under dry reaction conditions

An easy synthetic method was developed under dry reaction conditions for the preparation of terminal alkynes from 1,1-dibromoalkenes and in the presence of succinimide which acts as a nucleophile and proton donor. It was demonstrated with the synthesis of a broad spectrum of terminal alkynes and extended to synthesize internal alkynes under tandem reaction conditions.

Thermal decarboxylative Nazarov cyclization of cyclic enol carbonates involving chirality transfer

Decarboxylative Nazarov cyclization of chiral cyclic enol carbonates proceeded to afford chiral 2-cyclopentenones with excellent chirality transfer under thermal conditions without any catalyst. Interestingly, the thermal decarboxylative Nazarov cyclization furnished the desired product with better chirality transfer than the Lewis acid-catalyzed reaction.

Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with alkynes

The copper(ii)-catalyzed (4+1) cyclizations and copper(i)-catalyzed (3+2) cycloadditions of iodonium ylides and alkynes were successfully developed by employing efficient and safe iodonium ylides instead of traditional diazo compounds. Highly functionaliz

Fe-Catalyzed Selective Cyclopropanation of Enynes under Photochemical or Thermal Conditions

The nucleophilic Fe-complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the cyclopropanation of enynes to substituted propargyl cyclopropanes using diazoesters as carbene surrogates. The catalyst can be activated either thermally in the presence of catalytic amounts of 4-nitroanisole or under photochemical conditions. Cyclopropanation occurs selectively at the enyne moiety; alternative olefinic moieties remain intact.

Synthesis, in-situ membrane preparation, and good gas permselectivity of insoluble poly(substituted acetylene)s loosely cross-linked with short and soft siloxane and silanol linkages

Insoluble but membrane-formable poly(substituted acetylene)s loosely cross-linked by short and soft Si–O–Si and SiOH---(OH)Si linkages have been synthesized from the corresponding monomers having one or two SiOH groups. These monomers have been polymerized in homogeneous systems to produce homogeneous polymer solutions in toluene. The resulting solutions were cast on polytetrafuluoroethylene sheets followed by evaporation of the solvent to give tough and flexible membranes which were completely insoluble. The membranes showed good oxygen and carbon oxide permselectivity and their plots in PO2 vs PO2/PN2 graph exceeded the 1991 Robeson's upper bound and very close to the 2008 Robeson's upper bound. The excellent selectivity are caused by enhancement of diffusion selectivity by the soft network structure which can create small pores (i.e., ultramicro pores) based on the short linkages. No drop in permeability may be due to the soft Si–O–Si and SiOH---(OH)Si linkages. In addition no change in PO2 and PO2/PN2 by aging was observed.

Self-Assembly and Molecular Recognition in Water: Tubular Stacking and Guest-Templated Discrete Assembly of Water-Soluble, Shape-Persistent Macrocycles

Supramolecular chemistry in aqueous media is an area with great fundamental and practical significance. To examine the role of multiple noncovalent interactions in controlled assembling and binding behavior in water, the self-association of five water-soluble hexakis(m-phenylene ethynylene) (m-PE) macrocycles, along with the molecular recognition behavior of the resultant assemblies, is investigated with UV-vis, fluorescence, CD, and NMR spectroscopy, mass spectrometry, and computational studies. In contrast to their different extents of self-aggregation in organic solvents, all five macrocycles remain aggregated in water at concentrations down to the micromolar (μM) range. CD spectroscopy reveals that 1-F6 and 1-H6, two macrocycles carrying chiral side chains and capable of H-bonded self-association, assemble into tubular stacks. The tubular stacks serve as supramolecular hosts in water, as exemplified by the interaction of macrocycles 1-H6 and 2-H6 and guests G1 through G4, each having a rod-like oligo(p-phenylene ethynylene) (p-PE) segment flanked by two hydrophilic chains. Fluorescence and 1H NMR spectroscopy revealed the formation of kinetically stable, discrete assemblies upon mixing 2-H6 and a guest. The binding stoichiometry, determined with fluorescence, 1H NMR, and ESI-MS, reveals that the discrete assemblies are novel pseudorotaxanes, each containing a pair of identical guest molecules encased by a tubular stack. The two guest molecules define the number of macrocyclic molecules that comprise the host, which curbs the "infinite" stack growth, resulting in a tubular stack with a cylindrical pore tailoring the length of the p-PE segment of the bound guests. Each complex is stabilized by the action of multiple noncovalent forces including aromatic stacking, side-chain H-bonding, and van der Waals interactions. Thus, the interplay of multiple noncovalent forces aligns the molecules of macrocycles 1 and 2 into tubular stacks with cylindrical inner pores that, upon binding rod-like guests, lead to tight, discrete, and well-ordered tubular assemblies that are unprecedented in water.