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
• Article Data: 68

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

Description

1,4-BIS(PHENYLETHYNYL)BENZENE, also known as diphenylethynylbenzene, is an organic compound with a unique molecular structure that features a benzene ring with two phenylethynyl groups attached at the 1 and 4 positions. 1,4-BIS(PHENYLETHYNYL)BENZENE is known for its versatile chemical properties and potential applications in various fields.

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

• 106-37-6 1.4-dibromobenzene 
• 536-74-3 phenylacetylene 
• 589-87-7 1,4-bromoiodobenzene 
• 623-25-6 p-Xylylene dichloride 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 591-50-4 iodobenzene 
• 624-38-4 para-diiodobenzene 
• 250643-76-6 tris((2-phenyl)ethynyl)indium 
• 4440-01-1 lithium phenylacetylide 
• 17938-13-5 1,4-Bis(trimethylsilylethynyl)benzene 
• 603-36-1 triphenylantimony 
• 1719-19-3 2-Methyl-4-phenyl-3-butyn-2-ol 
• 247113-66-2 1,4-bis[(benzoyl)(tributylphosphoranylidene)methyl]benzene 
• 66107-30-0 4-bromophenyl trifluoromethanesulfonate 

Downstream Products

• 10273-55-9 1.4-Bis-1.2.4-triphenyl-fluorenonyl-⁽³⁾-benzol 
• 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 
• 54161-44-3 C₈₀H₅₄ 
• 13730-05-7 2',4',2''',6'''-Tetraphenyl-diacenaphtho<1.2-e',1'.2'-d'''>1.1',3'.1'',4''.1''',3'''.1''''-quinquephenyl 
• 1608-40-8 1,4-bis(2-phenylethyl)benzene 
• 1608-41-9 1,4-distyrylbenzene 
• 41758-31-0 3,3'-diphenyl-2,2'-p-phenylene-bis-quinoxaline 

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

Palladium-catalyzed reaction of phenylacetylene with aryl iodides in aqueous medium

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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

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.

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.