13667-12-4

Usage

General Description

4-Bromo diphenylacetylene, also known as 1-Bromo-4-ethynylbiphenyl, is a chemical compound with the molecular formula C14H9Br. It is a brominated derivative of diphenylacetylene, which is an important building block in organic synthesis. 4-Bromo diphenylacetylene is a yellow crystalline solid that is insoluble in water but soluble in organic solvents. It is primarily used as a building block in the synthesis of various organic compounds, such as pharmaceuticals and materials for electronic devices. Its bromine substituent makes it a useful reagent for organic reactions, providing additional versatility in organic synthesis. Additionally, 4-Bromo diphenylacetylene has been studied for its potential applications in materials science and nanotechnology due to its unique structure and properties.

InChI:InChI=1/C14H9Br/c15-14-10-8-13(9-11-14)7-6-12-4-2-1-3-5-12/h1-5,8-11H

Upstream product

• 201230-82-2 carbon monoxide 
• 589-87-7 1,4-bromoiodobenzene 
• 536-74-3 phenylacetylene 
• 6738-06-3 phenylethynylmagnesium bromide 
• 66107-30-0 4-bromophenyl trifluoromethanesulfonate 
• 106-37-6 1.4-dibromobenzene 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 591-50-4 iodobenzene 
• 476436-59-6 1-[2-(4-bromophenyl)ethynyl]-1H-1,2,3-benzotriazole 
• 5467-74-3 4-Bromophenylboronic acid 
• 250643-76-6 tris((2-phenyl)ethynyl)indium 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 7681-65-4 copper(I) iodide 
• 65826-67-7 bis(4-bromophenyl)iodonium bromide 

Downstream Products

• 136459-72-8 1-phenyl-2-acetylene 
• 13667-11-3 4-(Phenylethinyl)triphenylmethanol 
• 25347-37-9 Tris-(4-phenylethynyl-phenyl)-methanol 
• 122213-01-8 Phenyl-bis-(4-phenylethynyl-phenyl)-methanol 
• 150705-07-0 1-(p-N,N-diethylanilinyl)-2-phenylacetylene 
• 203639-82-1 4-Phenylethynyl-benzenesulfonyl chloride 
• 39229-12-4 4-bromobenzil 
• 146284-11-9 1-phenyl-2-(p-dimethylsilopropylsilyl)phenylacetylate 
• 146284-17-5 1-phenyl-2-(triethylsilyl)phenylacetylene 
• 850566-21-1 1-(p-(dimethyloctylsilyl)phenyl)-2-phenylacetylene 
• 850566-23-3 1-phenyl-2-(p-dimethyloctadecylsilyl)phenylacetylene 
• 4714-24-3 (Z)-1-(4-bromophenyl)-2-phenylethylene 
• 688792-66-7 (C₅H₅)Co(C₄(C₆H₅)3C₆H₄Br) 
• 1034330-14-7 5,5-dimethyl-2-[4-(phenylethynyl)phenyl]-1,3,2-dioxaborinane 

Relevant academic research and scientific papers

Palladium-catalyzed decarboxylative coupling reaction with alkynyl carboxylic acids and arylsiloxanes

A decarboxylative coupling reaction for alkynyl carboxylic acids and arylsiloxanes was developed using a palladium catalyst. This method provided the desired coupled products in moderate to good yields by reacting the alkynyl carboxylic acids and arylsiloxanes with Pd(dba)2(1.0?mol?%), 1,1-bis(diphenylphosphino)methane (1.0?mol?%), and AgF2(2.0?equiv) at 60?°C for 6?h.

Sonogashira reactions catalyzed by a new and efficient copper(I) catalyst incorporating N-benzyl DABCO chloride

A new and effective catalytic system using [N-benzyl DABCO] +[Cu4Cl5]- was developed for the palladium-free Sonogashira cross-coupling reactions of phenylacetylene with a variety of aryl halides. In this homogeneous catalytic system, 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride, a quaternary ammonium salt containing a coordinating center, plays an important role and increases the efficiency of Cu(I) species during the reaction. A number of internal alkynes were produced in moderate to excellent yields, in short reaction times in DMF at 135 °C.

Aggregates of a hetero-oligophenylene derivative as reactors for the generation of palladium nanoparticles: a potential catalyst in the Sonogashira coupling reaction under aerial conditions

The utilization of Pd nanoparticles stabilized by aggregates of hetero-oligophenylene derivative 3 as an excellent catalyst in a copper/amine free Sonogashira coupling reaction under aerial conditions at room temperature has been demonstrated.

Ligand-free palladium-catalyzed decarboxylative coupling reactions of aryl iodides and alkynyl carboxylic acids

Pd-CNT nanocomposite was prepared from the composite of thiolated MWNT and Na2PdCl4. The palladium nanoparticles possess an average diameter of 2.9 nm with a narrow size distribution for the Pd-CNT. This Pd-CNT showed good activities in the coupling reactions of aryl iodides and aryl alkynyl carboxylic acids to produce the diaryl alkynes in good yields without any additional ligand.

Copper(I) complexes of 2-(benzen-1-yl)methyleneamino-3-aminomaleonitrile and triphenylphosphine ligands: synthesis, characterization, luminescence and catalytic properties

Some mixed ligand copper(I) complexes of general formula [Cu(L)(PPh3)3]X (X?=?Cl (1), ClO4 (2), BF4 (3) or PF6 (4); L?=?2-(benzen-1-yl)methyleneamino-3-aminomaleonitrile) were prepared and characterized by physicochemical and spectroscopic methods. A single-crystal X-ray diffraction study of [Cu(L)(PPh3)3]CIO4 (2) revealed that the copper atom is four coordinated in a distorted tetrahedral geometry. Electrochemical studies of complexes 1–4 show quasireversible redox behavior corresponding to the Cu(I)/Cu(II) couple. Room temperature luminescence is observed for all four complexes. These complexes proved to be effective catalysts for the Sonogashira coupling of terminal alkynes with aryl halides at 90?°C.

Synthesis and spectral properties of novel iminophosphoranes

Three new iminophosphoranes coded as FPZ1 (Ph–C≡C–C6H4–N = PPh3), FPZ2 (Ph–N = P(C6H4–C≡C–Ph)3) and FPZ3 (Ph–C≡C–C6H4–N = P(C6H4–C≡C–Ph)3) were designed and synthesized by introducing different numbers of phenylene acetylene units to FPZ0 (Ph–N = PPh3). The effect of structural modification was studied in detail analyzing the absorption spectra, the emission spectra, and the distributions of the electron density. The absorption spectra of the new iminophosphoranes are shown to be a linear combination of the spectra of each part by the artificial combinatorial absorption spectrum, which coincides with the real one. Most probably the individual parts can’t conjugate due to the tetrahedral structure. The probably formed excimer of FPZ0 and FPZ1 causes in their solid emission spectra an obvious bathochromic shift as compared to that of FPZ2 and FPZ3. The melting point data also showed that long branches of FPZ2 and FPZ3 will attenuate the interactions between the molecules. The results of quantum chemical calculations show that the electronic density in the HOMO of FPZ1, FPZ2, and FPZ3 is delocalized over the iminoaryl moieties. The electron density in the LUMO is delocalized over the triaryl phosphine moieties, but only concentrated on two branches, which directly determines the main direction of intramolecular charge transfer.

Synthesis and optical properties of cationic cyclopentadienyl iron complexes with diphenylacetylene chromophores

Cationic cyclopentadienyl iron complexes of arenes are applied in photopolymerization and photocatalysis because of their good photophysical and photochemical properties. In this study, a series of cationic cyclopentadienyl iron complexes with diphenylace

Pd(II)–acylthiourea complex and its immobilized counterpart catalyzed condensation of phenylacetylene with aryl halides

New Pd(II) complex, trans-[PdCl2L2] (1) (L = N-carbamothioylthiophene-2-carboxamide), was prepared and characterized. Its heterogeneous counterpart, trans-[PdCl2(L-SNPs)2] (2) (L-SNPs = ligand immobilized on silica nanoparticles), was also prepared through covalent modification of the ligand using silica nanoparticles and characterized. Both 1 and 2 were exploited for their catalytic activity towards condensation of phenylacetylene with aryl halides. The complexes exhibited good activity when aryl halide bears I? or Br? group. Further, catalyst 2 can be reused for four cycles.

Synthesis of internal alkynes by Pd(PPh3)4/TMEDA-catalyzed Kumada cross-coupling of alkynyl halides with grignard reagents

Alkynes serve as prevalent intermediates in the synthesis of natural products and pharmaceuticals. We here described a new and efficient route to internal alkynes by Pd-catalyzed Kumada cross-coupling reactions of alkynyl halides with Grignard reagents. In the presence of Pd(PPh3)4 and N 1,N 1,N 2,N 2-tetramethylethane-1,2-diamine (TMEDA), a variety of alkynyl halides underwent Kumada coupling with Grignard reagents, giving the corresponding internal alkynes in moderate to good yields. A new Pd-catalyzed Kumada cross-coupling reaction of alkynyl halides with Grignard reagents has been developed. This transformation provides a new, experimentally simple access to internal alkynes in good yields, and it can accommodate a broad range of substrates with excellent functional group tolerance and good levels of selectivity control.

DNA-Decorated, Helically Twisted Nanoribbons: A Scaffold for the Fabrication of One-Dimensional, Chiral, Plasmonic Nanostructures

Crafting of chiral plasmonic nanostructures is extremely important and challenging. DNA-directed organization of nanoparticle on a chiral template is the most appealing strategy for this purpose. Herein, we report a supramolecular approach for the design of DNA-decorated, helically twisted nanoribbons through the amphiphilicity-driven self-assembly of a new class of amphiphiles derived from DNA and hexaphenylbenzene (HPB). The ribbons are self-assembled in a lamellar fashion through the hydrophobic interactions of HPB. The transfer of molecular chirality of ssDNA into the HPB core results in the bias of one of the chiral propeller conformations for HPB and induces a helical twist into the lamellar packing, and leads to the formation of DNA-wrapped nanoribbons with M-helicity. The potential of the ribbon to act as a reversible template for the 1D chiral organization of plasmonic nanomaterials through DNA hybridization is demonstrated.