118688-56-5

Basic information

• Product Name: 1,3,5-TRIS(PHENYLETHYNYL)BENZENE
• Synonyms: 1,3,5-TRIS(PHENYLETHYNYL)BENZENE;Trisphenylethynylbenzene;1,3,5-Tri(phenylethynyl)benzene
• CAS NO: 118688-56-5
• Molecular Formula: C₃₀H₁₈
• Molecular Weight: 378.46
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives
• Mol File: 118688-56-5.mol

Chemical Properties

• Melting Point: 141-142 °C
• Boiling Point: 603.17 °C at 760 mmHg
• Flash Point: 319.206 °C
• Appearance: /
• Density: 1.19 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.705
• CAS DataBase Reference: 1,3,5-TRIS(PHENYLETHYNYL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-TRIS(PHENYLETHYNYL)BENZENE(118688-56-5)
• EPA Substance Registry System: 1,3,5-TRIS(PHENYLETHYNYL)BENZENE(118688-56-5)

Safety Data

• Statements: 10-20/21/22-36/37/38
• Safety Statements: 16-26-36
• RIDADR: 1993
• Hazardous Substances Data: 118688-56-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
1,3,5-Tris(phenylethynyl)benzene is used as a key ingredient in various chemical applications due to its highly stable and rigid characteristics. Its unique structure makes it suitable for use in the synthesis of advanced materials and compounds.
Used in Material Science:
In the field of material science, 1,3,5-Tris(phenylethynyl)benzene is utilized as a building block for the development of novel materials with specific properties. Its rigid and stable nature allows for the creation of materials with improved mechanical, thermal, and electrical characteristics.
Used in Pharmaceutical Industry:
1,3,5-Tris(phenylethynyl)benzene may also find applications in the pharmaceutical industry as a potential precursor for the synthesis of new drug molecules. Its unique structure could be leveraged to develop compounds with specific therapeutic properties.
Used in Research and Development:
TPEB is employed in research and development settings to explore its potential applications and properties. Scientists and researchers use this compound to investigate its behavior in various chemical reactions and to understand its interactions with other molecules.

InChI:InChI=1/C30H18/c1-4-10-25(11-5-1)16-19-28-22-29(20-17-26-12-6-2-7-13-26)24-30(23-28)21-18-27-14-8-3-9-15-27/h1-15,22-24H

Upstream product

• 626-39-1 1,3,5-trisbromobenzene 
• 250643-76-6 tris((2-phenyl)ethynyl)indium 
• 626-44-8 1,3,5-Triiodobenzene 
• 536-74-3 phenylacetylene 
• 1719-19-3 2-Methyl-4-phenyl-3-butyn-2-ol 

Downstream Products

• 1351008-19-9 1,3,5-tris(3-phenylnaphthalen-2-yl)benzene 

Relevant articles and documents

Structures of bis- and tris(2-phenyl-o-carboran-1-yl)benzenes. Construction of three-dimensional structures converted from planar arylacetylenic arrays

Compounds (1-3), which are composed of benzene nuclei linked through 1,2-dicarba-closo-dodecaborane (o-carborane), were synthesized and their structures were determined by X-ray crystallography. 1,3-Bis(2-phenyl-o-carboran-1-yl)benzene and 1,3,5-tris(2-ph

Multifold and sequential cross-coupling reactions with indium organometallics

Multifold and sequential palladium-catalyzed cross-coupling reactions can be performed between triorganoindium compounds and oligohaloarenes using only a small excess of the organometallic reagent, low catalyst charge loading and short reaction times.

Synthesis and X-ray structure of 1,3,5-tri(phenylethynyl)benzene

1,3,5-Tri(phenylethynyl)benzene 1 obtained by coupling triiodobenzene with phenyl-acetylene shows an unusual non planar molecular structure.

Pd Nanoparticles Immobilized on Nanosilica Triazine Dendritic Polymer: A Reusable Catalyst for the Synthesis of Mono-, Di-, and Trialkynylaromatics by Sonogashira Cross-Coupling in Water

Palladium nanoparticles immobilized on nano-silica triazine dendritic polymer (Pdnp-nSTDP) was found to be a highly effective catalyst for the Sonogashira cross-coupling of aryl halides (iodides, bromides, and chlorides) with aromatic and aliphatic terminal alkynes. This reaction was best performed in water as a green solvent in the presence of just 0.01 mol-% of the catalyst at room temperature. Efficient synthesis of V- and star-shaped polyalkynylated molecules with a benzene, pyridine, or pyrimidine central core was also achieved through Sonogashira cross-coupling of dihalo and trihalo aromatics with terminal alkynes in the presence of this catalytic system. The Pdnp-nSTDP catalyst was easily recovered and reused several times without significant loss of reactivity.

Gold and palladium combined for the Sonogashira coupling of aryl and heteroaryl halides

A highly efficient gold and palladium combined methodology for the Sonogashira coupling of a wide array of electronically and structurally diverse aryl and heteroaryl halides is described. The orthogonal reactivity of the two metals shows high selectivity and extreme functional group tolerance in Sonogashira coupling. A brief mechanistic study reveals that the gold acetylide intermediate enters into the palladium catalytic cycle at the transmetalation step. Georg Thieme Verlag Stuttgart.New York.

Palladium-catalyzed multialkynyl cross-coupling reactions with tetraalkynylindates

An efficient Pd-catalyzed multialkynyl cross-coupling reaction performed with tetraalkyriylindates generated in situ from the reaction of 1 equiv. of indium trichloride with 4 equiv. of organometallic reagents has been developed to produce symmetric as well as unsymmetric multialkynyl-substituted aromatic compounds in good-to-excellent yields. In these reactions, the four acetylide groups in the tetraalkynylindates transferred effectively to a variety of aryl bromides.

Palladium-catalyzed copper-free sonogashira coupling reaction in water and acetone

An efficient palladium-catalyzed copper-free Sonogashira reaction in water and acetone has been developed under mild conditions. The results showed that the aryl iodides could carry out the cross-coupling reaction with a variety of terminal alkynes in high yields in water-acetone in the absence of amine, copper(I) salts, or phosphine ligands at 60°C for one hour, and good yields were obtained for aryl bromides at 60°C for 12-24 hours in the presence of triphenylphosphine and piperidine. The method could be used to synthesize polyethynyl aromatic compounds in a one-pot reaction. Georg Thieme Verlag Stuttgart.

Rigid molecular architectures that comprise a 1,3,5-trisubstituted benzene core and three oligoaryleneethynylene arms: Light-emitting characteristics and π conjugation between the arms

In view of increasing interest in light-emitting materials, we have investigated the light-emitting characteristics and occurrence of conjugation between arms of star-shaped rigid molecules that comprise a 1,3,5-triethynylbenzene core and methoxy group-su

New synthetic applications of indium organometallics in cross-coupling reactions

The use of indium organometallics in multifold and sequential cross-coupling reactions is reported. Triorganoindium reagents (R3In) react, under palladium catalysis, with oligohaloarenes affording the multiple cross-coupling products in a single operation. In the reaction, the three organic groups (alkyl, aryl, alkenyl or alkynyl) attached to indium are efficiently transferred to the electrophile, with only a slight excess of organometallic reagent. We demonstrate that indium organometallics are useful reagents for sequential cross-coupling reactions. This reaction illustrates the high chemoselectivity of R3In. Georg Thieme Verlag Stuttgart.

Palladium-catalyzed cross-alkynylation of aryl bromides by sodium tetraalkynylaluminates

Sodium tetraalkynylaluminates (1-4), prepared from NaAlH4 and terminal alkynes, cross-couple with aryl bromides in the presence of Pd(0) and Pd(II) catalysts. The reactions take place in boiling THF or DME. The process is applicable to both hom