80221-11-0

Usage

Uses

Used in Organic Synthesis:
1,2-DI-(4-N-BUTYLPHENYL)ACETYLENE is utilized as a building block in organic synthesis for the creation of various complex organic compounds. Its structural attributes make it a key component in the assembly of molecules with specific functionalities and properties.
Used in Materials Science:
In the field of materials science, 1,2-DI-(4-N-BUTYLPHENYL)ACETYLENE is used as a precursor for developing new materials with tailored characteristics. Its aromatic and conjugated features contribute to the advancement of materials with improved electronic and optical properties.
Used in Pharmaceutical Research:
1,2-DI-(4-N-BUTYLPHENYL)ACETYLENE serves as an intermediate in pharmaceutical research, where it aids in the development of novel drug candidates. Its unique structure can be leveraged to design molecules with specific biological activities, potentially leading to new therapeutic agents.
Used in Electronics and Optoelectronics:
1,2-DI-(4-N-BUTYLPHENYL)ACETYLENE is employed in the electronics and optoelectronics industry due to its potential utility in the fabrication of electronic devices and optoelectronic components. Its conjugated system and aromatic nature are advantageous for enhancing the performance of these devices.

InChI:InChI=1/C22H26/c1-3-5-7-19-9-13-21(14-10-19)17-18-22-15-11-20(12-16-22)8-6-4-2/h9-16H,3-8H2,1-2H3

Upstream product

• 75-20-7 calcium carbide 
• 72302-28-4 4-n-butylbenzenediazonium tetrafluoroborate 
• 41492-05-1 p-bromobutylbenzene 
• 79887-09-5 (4-butylphenyl)acetylene 
• 202524-78-5 1-(4-butylphenyl)-2-trimethylsilylacetylene 
• 1066-54-2 trimethylsilylacetylene 
• 15499-27-1 4-n-butylchlorobenzene 
• 471-25-0 Propiolic acid 
• 20651-67-6 4-butyliodobenzene 
• 28788-62-7 4-butylbenzoyl chloride 
• 994-71-8 bis(tributylstannyl)acetylene 
• 857823-99-5 1,1-bis-(4-butyl-phenyl)-2-chloro-ethene 

Downstream Products

• 1313221-10-1 2,3-bis(4-butylphenyl)-4,5-di-p-tolylfuran 
• 1313221-01-0 2,3,4,5-tetrakis(4-butylphenyl)furan 
• 99643-62-6 2,3,4,5-tetra-p-tolylfuran 
• 1313221-06-5 2,3-bis(4-butylphenyl)-4,5-diphenylfuran 
• 1056-77-5 2,3,4,5-tetraphenylfuran 
• 1025014-21-4 2,3,4,5-tetrakis[4-(trifluoromethyl)phenyl]furan 
• 1313221-13-4 2,3-bis(4-butylphenyl)-4,5-bis(4-(trifluoromethyl)phenyl)furan 
• 1446486-57-2 2,3-bis(4-butylphenyl)benzofuran 
• 1469444-96-9 (Z)-1-butyl-4-(2-phenyl-2-p-butylphenylvinyl)benzene 
• 1469445-26-8 (E)-1-butyl-4-(2-phenyl-2-p-butylphenylvinyl)benzene 
• 1514905-19-1 C₂₂H₂₈O 

Relevant academic research and scientific papers

Synthesis of Diarylethynes from Aryldiazonium Salts by Using Calcium Carbide as an Alkyne Source in a Deep Eutectic Solvent

An efficient method for the synthesis of diarylethynes from aryldiazonium salts by using calcium carbide as an alkyne source at room temperature in a deep eutectic solvent is described. The salient features of this protocol are an inexpensive and easy-to-handle alkyne source, a nonvolatile and recyclable solvent, mild conditions, and a simple workup procedure.

Synthesis of substituted helicenes by Ir-catalyzed annulative coupling of biarylcarboxylic acid chlorides with alkynes

A series of substituted [4] and [5]helicenes were synthesized in moderate to good yields by an Ir-catalyzed annulative coupling of biarylcarboxylic acid chlorides with internal alkynes, which involves facile C-H bond cleavage and decarbonylation. The double annulative coupling of 1, 1′:5′, 1″-ternaphthalene- 2, 2″-dicarboxylic acid dichloride with 4-octyne was also accomplished to give rise to an S-shaped double helicene. Unexpectedly, a π-extended benzofluoranthene-merged [5]- helicene was constructed through the annulative coupling and the successive C(aryl)-C(aryl) bond forming reaction when 1, 1′:4′, 1″-ternaphthalene-2, 2″-dicarboxylic acid dichloride was employed as the substrate. The crystal structure and the optical properties of the latter unique product were also investigated.

Synthesis and Characterization of Polycyclic Aromatic Hydrocarbons with Different Spatial Constructions Based on Hexaphenylbenzene Derivatives

In recent years, low-bandgap polymers have attracted much attention in a wide range of fields. The synthesis of these compounds has been focused on three factors according to the Roncali bandgap theory: 1) the degree of bond-length alternation (Eδr), 2) the aromatic resonance energy of the cycle (ERes), and 3) the substituted groups (ESub). Herein, we have designed and prepared low-bandgap polymers in a different way by using the factors Eθ (the deviation from planarity of the polymer chain) and EInt (the interaction of the molecular chains in the solid state). Thus, three polycyclic aromatic hydrocarbons with different spatial constructions, based on hexaphenylbenzene derivatives, were prepared in this work: linear (P1-OX), V (P2-OX), and zigzag (P3-OX) types. These well-defined polymers exhibited interesting optical and electrochemistry behavior due to their different extents of planarity. Matrix-assisted laser desorption ionization time-of-flight mass spectrometry gave the incremental orderly molecular weight distributions of P1, P2, and P3, the weight-average molecular weights ((Formula presented.)) of which were 9000, 5500, and 69 000, respectively. Their lamellar layer structures and π–π intermolecular stacking were demonstrated by using two-dimensional grazing-incidence X-ray diffraction, which revealed the edge-on chain conformation. Finally, the materials were perfectly adapted to fabricate high-performance organic field-effect transistor devices, which revealed that these compounds could have great prospects as semiconductors.

Synthesis of substituted [8]cycloparaphenylenes by [2 + 2 + 2] cycloaddition

A new modular approach to the smallest substituted cycloparaphenylenes (CPPs) is presented. This versatile method permits access to substituted CPPs, choosing the substituent at a late stage of the synthesis. Variously substituted [8]CPPs have been synthesized, and their properties analyzed. The structural characteristics of substituted CPPs are close to those of unsubstituted CPPs. However, their optoelectronic behavior differs remarkably due to the larger torsion angle between the phenyl units.

Synthesis of diarylalkynes via tandem Sonogashira/decarboxylative reaction of aryl chlorides with propiolic acid

A facile and efficient protocol for one-pot synthesis of diarylalkynes via tandem Sonogashira/decarboxylative coupling has been developed. The remarkable features of this reaction include using commercially available aryl chlorides as starting materials and taking the propiolic acid instead of expensive terminal alkynes as an acetylene source. This journal is the Partner Organisations 2014.

Ambient arylmagnesiation of alkynes catalysed by ligandless nickel(ii)

A simple and efficient catalytic arylmagnesiation of diarylacetylenes and aryl(alkyl)acetylenes is accomplished by NiCl2·6H2O at r.t. in the absence of stabilising ligands. The corresponding tetra-substituted alkenes can be obtained in good yields by subsequent treatment with different electrophiles. The Royal Society of Chemistry 2013.

Utility of dysprosium as a reductant in coupling reactions of acyl chlorides: The synthesis of amides and diaryl-substituted acetylenes

Reduction of acyl chlorides with dysprosium metal has been studied. The reducing ability of dysprosium metal is solvent-dependent. Dysprosium metal, which requires neither any additive nor pretreatment, can promote the cross-coupling of acyl chlorides in DMF or DEF to give amides in good yields. When the reaction was performed in N,N-dimethylacetamide, the reductive self-coupling reaction of aroyl chloride took place smoothly and afforded the diaryl-substituted acetylenes in moderate to good yield.

Symmetric diarylacetylenes: One-pot syntheses and solution photoluminescence

Bis(tri-n-butylstannyl)acetylene was synthesized and used to create a series of symmetric diarylacetylenes via a one-step Stille coupling protocol with Pd(PPh3)4 as the catalyst. In many cases, the product simply crystallized in good yields from the reaction mixture upon cooling after reflux at 100 °C or upon removal of solvent. The diarylacetylenes were studied using UV-vis and fluorescence spectroscopies, which showed that naphthyl- and biphenyl-substituted acetylenes had very high solution-state fluorescence quantum yields.