1849-27-0

Basic information

• Product Name: 1,4-BIS(PHENYLETHYNYL)BENZENE
• Synonyms: 1,4-BIS(PHENYLETHYNYL)BENZENE;TIMTEC-BB SBB008837;1,4-bis-(PHENYLETHYNYL)BENZENE 97%;Benzene,1,4-bis(2-phenylethynyl)
• CAS NO: 1849-27-0
• Molecular Formula: C₂₂H₁₄
• Molecular Weight: 278.35
• Mol File: 1849-27-0.mol

Chemical Properties

• Melting Point: 176 °C
• Boiling Point: 446.3 °C at 760 mmHg
• Flash Point: 219.8 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 9.71E-08mmHg at 25°C
• Refractive Index: 1.674
• CAS DataBase Reference: 1,4-BIS(PHENYLETHYNYL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-BIS(PHENYLETHYNYL)BENZENE(1849-27-0)
• EPA Substance Registry System: 1,4-BIS(PHENYLETHYNYL)BENZENE(1849-27-0)

Safety Data

• Hazardous Substances Data: 1849-27-0(Hazardous Substances Data)

Usage

Uses

1. Used in Organic Synthesis:
1,4-BIS(PHENYLETHYNYL)BENZENE is used as a key intermediate in the one-pot synthesis of 1,2,3-triphospholide anions, which are important building blocks for the development of novel materials with unique properties. The compound's ethynyl groups facilitate the formation of these anions through a series of chemical reactions.
2. Used in the Production of Conjugated Microporous Polymers:
1,4-BIS(PHENYLETHYNYL)BENZENE is also utilized as a precursor in the synthesis of conjugated microporous polymers. These polymers have potential applications in gas storage, separation, and sensing due to their porous structure and conjugated nature. The phenylethynyl groups in the compound contribute to the formation of the polymer's backbone, which is essential for its functionality.

Synthesis Reference(s)

Tetrahedron Letters, 16, p. 4467, 1975 DOI: 10.1016/S0040-4039(00)91094-3

InChI:InChI=1/C22H14/c1-3-7-19(8-4-1)11-13-21-15-17-22(18-16-21)14-12-20-9-5-2-6-10-20/h1-10,15-18H

Upstream product

• 55006-58-1 1,4-bis(phenylethynyl)-2,5-cyclohexadiene-1,4-diol 
• 102703-92-4 1,4-bis-(α,β-dibromo-phenethyl)-benzene 
• 935-14-8 1,4-diethynylbenzene 
• 1538-62-1 triphenylantimony(V) diacetate 
• 603-33-8 triphenylbismuthane 
• 77295-67-1 1,4-bis(2,2-dibromoethenyl)benzene 
• 589-87-7 1,4-bromoiodobenzene 
• 536-74-3 phenylacetylene 
• 106-37-6 1.4-dibromobenzene 
• 250643-76-6 tris((2-phenyl)ethynyl)indium 
• 624-38-4 para-diiodobenzene 
• 4440-01-1 lithium phenylacetylide 
• 17938-13-5 1,4-Bis(trimethylsilylethynyl)benzene 
• 603-36-1 triphenylantimony 

Downstream Products

• 1006709-36-9 3,4-diphenyl-5-[4-(phenylethynyl)phenyl]-3H-1,2,3-diselenaphosphole 3-selenide 
• 1006709-37-0 5,5'-(1,4-phenylene)bis(3,4-diphenyl-3H-1,2,3-diselenaphosphole) 3,3'-diselenide 
• 1198116-30-1 11,12-dimethyl-5-phenyl-6-(4-(2-phenylethynyl)phenyl)-11H,12H-indolo[2,3-a]carbazole 
• 25423-83-0 1,4-bis(3-phenylquinoxalin-2-yl)benzene 
• 3432-73-3 3,3'-(1,4-phenylene)bis(2,4,5-triphenylcyclopenta-2,4-dien-1-one) 
• 52375-28-7 [(Co₂(CO)6)2(PhC_.tplbond.C-(p-C₆H₄)-C_.tplbond.CPh)] 
• 55043-09-9 6-Phenethyl-1-(4-phenethyl-phenyl)-2,3-diphenyl-azulene 
• 3363-97-1 1,4-bis(phenylglyoxalyl)benzene 
• 70734-74-6 1-(phenylglyoxaloyl)-4-(phenylethynyl)benzene 
• 10273-55-9 1.4-Bis-1.2.4-triphenyl-fluorenonyl-⁽³⁾-benzol 
• 3364-01-0 2',2''',3',3''',5',5''',6',6'''-octaphenyl-p-quinquephenyl 
• 55006-59-2 1,2-Diphenyl-6-phenylethynyl-3-(4-phenylethynyl-phenyl)-azulene 
• 55006-60-5 1,2-Diphenyl-6-phenylethynyl-3-(4-phenylethynyl-phenyl)-naphthalene 
• 1985-58-6 1,4-bis(2-phenylethyl)benzene 

Relevant articles and documents

A re-evaluation of the photophysical properties of 1,4-bis(phenylethynyl)benzene: A model for poly(phenyleneethynylene)

Photophysical measurements, recorded in aerated cyclohexane at 283 K, indicate that 1,4-bis-(phenylethynyl)benzene behaves in a conventional manner, undergoing emission from the lowest vibrational level of the first excited singlet state; there is no evid

Choline chloride/CuCl as an effective homogeneous catalyst for palladium-free Sonogashira cross-coupling reactions

Choline chloride-CuCl (ChCl-CuCl) has been employed as an efficient catalytic system in the palladium-free Sonogashira-type cross-coupling reactions of phenylacetylene with a variety of aryl halides. Choline chloride, as an effective ligand and a quaterna

From branched hydrocarbon propellers to C3-symmetric graphite disks

Branched hydrocarbon propellers (9 and 12) were prepared by stepwise palladium-catalyzed Hagihara-Sonogashira coupling reactions and Diels-Alder cycloadditions and submitted to oxidative cyclodehydrogenation by FeCl 3 to afford two new giant graphite disks 2 and 3 with 3-fold symmetry in high yield. One of the precursors, the polyphenylene dendrimer 9 containing 150 carbon atoms, was crystallographically characterized. The poorly soluble graphite disks were characterized by isotope-resolved MALDI-TOF mass spectroscopy, and their electronic and vibrational properties were investigated by solid-state UV-vis and Raman spectroscopy. The effect of molecular size and geometry on their properties was discussed. The molecule 2 represents the largest, 3-fold-symmetric all-benzenoid graphite disk, and the five-membered rings in molecule 3 open the opportunity to synthesize large bowl-shaped PAHs.

Facile one-pot synthesis of diarylacetylenes from arylaldehydes: Via an addition-double elimination process

A practical one-pot protocol has been developed to synthesize diarylacetylenes from arylaldehydes by treatment with 1-(arylmethyl)benzotriazoles and LiN(SiMe3)2. The reaction proceeded through imine formation, Mannich-type addition and double elimination to deliver products in up to 99% yields with broad substrate scope. In addition, gram-scale synthesis of 1-bromo-4-(phenylethynyl)benzene has been demonstrated.

Immobilized Pd on a NHC-functionalized metal-organic FrameworkMIL-101(Cr): An efficient heterogeneous catalyst in the heck and copper-free Sonogashira coupling reactions

A heterogeneous palladium catalyst system based on immobilization of palladium moieties on a N-heterocyclic carbene (NHC) modified metal organic framework (MOF) was developed for the Heck and copper-free Sonogashira coupling reactions. In order to prepare this catalyst system, first, MIL-101(Cr) was functionalized with NHC moieties through a post synthetic modification (PSM) approach, and then Pd metal was stabilized on the prepered MIL-101(Cr)-NHC substrate. This material was characterized using various microscopic and spectroscopic techniques and then was used as an efficient heterogeneous Pd catalyst system in the Heck and copper-free Sonogashira reactions. Results of the heterogeneity tests showed that the Pd-NHC-MIL-101(Cr) catalyst can efficiently catalyzed these coupling reactions heterogeneously and no remarkable changes observed in the morphology and structure of MIL-101(Cr) template during the reaction progress. Also, existence of palladium nanoparticles immobilized on the MOF structure affirmed by the TEM and XPS analysis confirmed the oxidation state of Pd. A variety of alkene and alkyne derivatives were synthesized in good to excellent yields using this heterogeneous Pd catalyst system under normal conditions. More importantly Pd-NHC-MIL-101(Cr) catalyst was simply recovered from the reaction medium without remarkable decreasing in its catalytic activities after five times of reusability. The ICP analysis showed the very low Pd and Cr metals leaching, representing high stability and applicability of this catalyst in Pd coupling reactions.

Decorated palladium nanoparticles on mesoporous organosilicate as an efficient catalyst for Sonogashira coupling reaction

Abstract: Reforming mesoporous silica was provided by the reaction of SBA‐15 with (3-aminopropyl)triethoxysilane, the product of which was treated with furfural to give SBA-propyl-imine-furan. In the next step, palladium chloride was attached to the funct

Selective Synthesis of Non-Aromatic Five-Membered Sulfur Heterocycles from Alkynes by using a Proton Acid/N-Chlorophthalimide System

A multicomponent strategy to achieve two different regioselectivities from alkynes, isothiocyanates and H2O with a proton acid/N-chlorophthalimide (NCPI) system is described to selectively obtain non-aromatic five-membered sulfur heterocycles (1,3-oxathiol-2-imines/thiazol-2(3H)-one derivatives) through multiple bond formations. The process features readily available starting materials, mild reaction conditions, broad substrate scope, good functional-group tolerance, high regio- and chemo- selectivities, gram-scale synthesis and late-stage modifications. Mechanistic studies support the proposal that the transformation process includes a combination of H2O and isothiocyanate, free-radical formation, carbonation and intramolecular cyclization to give the products. Furthermore, the 1,3-oxathiol-2-imine derivatives possess unique fluorescence characteristics and can be used as Pd2+ sensors with a “turn-off” response, demonstrating potential applications in environmental and biological fields.

Simple and efficient diaryl alkyne synthesis method

The embodiment of the invention discloses a simple and efficient diaryl alkyne synthesis method. The method comprises the steps of by taking arylmethylbenzotriazole and aromatic aldehyde as raw materials, carrying out addition and double-beta-elimination reaction under the action of bis (trimethylsilyl) amino salt MN (SiMe3) 2 to synthesize diaryl alkyne by a one-pot method. The raw materials and chemical reagents used in the method are easy to obtain, the reaction conditions are mild, the operation is simple, the substrate universality is good, the product yield is high, and the method is a simple and efficient diaryl alkyne synthesis method.

Cu2O Nanocrystals-Catalyzed Photoredox Sonogashira Coupling of Terminal Alkynes and Arylhalides Enhanced by CO2

Herein the first visible-light-activated Sonogashira C?C coupling reaction at room temperature catalyzed by single-metal heterogeneous Cu2O truncated nanocubes (Cu2O TNCs) was developed. A wide variety of aryl halides and terminal alkynes worked well in this recyclable heterogeneous photochemical process to form the corresponding Sonogashira C?C coupling products in good yields. Mechanistic control studies indicated that CO2 enhances the formation of light-absorbing heterogeneous surface-bound CuI-phenylacetylide (λmax=472 nm), which further undergoes single-electron transfer with aryl iodides/bromides to enable Sonogashira Csp2 ?Csp bond formation. In contrast to literature-reported bimetallic TiO2-containing nanoparticles as photocatalyst, this work avoided the need of cocatalysis by TiO2. Single-metal CuI in Cu2O TNCs was solely responsible for the observed Csp2 ?Csp coupling reactions under CO2 atmosphere.

Sequentially Pd/Cu-Catalyzed Alkynylation-Oxidation Synthesis of 1,2-Diketones and Consecutive One-Pot Generation of Quinoxalines

We report a simple and efficient one-pot synthesis of 1,2-diketones by concatenation of two Pd/Cu-catalyzed processes: Pd0/CuI-catalyzed Sonogashira coupling of terminal alkynes with aryl (pseudo)halides furnishes internal alkynes, which are directly transformed by PdII/CuII-catalyzed Wacker-type oxidation with DMSO and oxygen as dual oxidants to furnish 1,2-diketones. With this efficient, catalyst economical process, various aryl iodides and triflates are efficiently transformed in high yields into symmetrically and unsymmetrically substituted 1,2-diketones with various functional groups. This process can be readily extended to a consecutive one-pot synthesis of quinoxalines in a diversity-oriented fashion.