612-71-5

Usage

Uses

1. Used in Chemical Sensing Applications:
1,3,5-Triphenylbenzene is used as a selective Cu2+ sensor in aqueous media. This application takes advantage of its chemical properties to detect and measure the presence of copper ions in various solutions, which is particularly useful in environmental monitoring and industrial processes.
2. Used in Fluorescent Materials:
Due to its inherent fluorescent properties, 1,3,5-Triphenylbenzene can be utilized in the development of fluorescent materials for various applications, such as in the field of bioimaging, where it can be used to label and track specific molecules or cellular structures.
3. Used in Organic Synthesis:
1,3,5-Triphenylbenzene can serve as a valuable building block in organic synthesis, particularly in the creation of more complex organic molecules with potential applications in pharmaceuticals, agrochemicals, and materials science.
4. Used in Analytical Chemistry:
1,3,5-Triphenylbenzene's unique chemical properties make it a useful tool in analytical chemistry for the detection and quantification of various substances, including metal ions and other small molecules.
5. Used in Research and Development:
1,3,5-Triphenylbenzene can be employed in research and development settings to study its properties and potential applications, as well as to develop new methods for its synthesis and use in various industries.

Purification Methods

Purify it by chromatography on alumina using *benzene or pet ether as eluents. Crystallise the triphenylbenzene from EtOH (m 174o). [Beilstein 5 H 737, 5 I 370, 5 II 670, 5 III 2563, 5 IV 2732.]

InChI:InChI=1/C24H18/c1-4-10-19(11-5-1)22-16-23(20-12-6-2-7-13-20)18-24(17-22)21-14-8-3-9-15-21/h1-18H

Upstream product

• 512-85-6 ascaridole 
• 618-34-8 1-chlorostyrene 
• 4316-37-4 1,1,-diethoxy-1-phenylethane 
• 40088-97-9 (1,3-diphenyl-but-3-enylidene)-phenyl-amine 
• 142-04-1 aniline hydrochloride 
• 22379-62-0 potassium benzyloxide 
• 122-78-1 phenylacetaldehyde 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 118-92-3 anthranilic acid 
• 75-36-5 acetyl chloride 
• 536-74-3 phenylacetylene 
• 15719-64-9 methylammonium carbonate 
• 62-53-3 aniline 
• 98-86-2 acetophenone 

Downstream Products

• 7371-00-8 2,4,6-Triphenyl-benzophenon 
• 6297-08-1 1,3,5-tricyclohexyl-cyclohexane 
• 234079-32-4 1,3,5-e,e,e-triphenylcyclohexane 
• 28336-57-4 1,3,5-a,e,e-triphenylcyclohexane 
• 1165-53-3 1,2,4-triphenylbenzene 
• 10368-73-7 2-bromo-1,3,5-triphenylbenzene 
• 17342-60-8 1,3,5-triphenylcyclohexane 
• 727430-35-5 [Mo(η6-1,3,5-triphenylbenzene)(CO)3] 
• 43175-61-7 (1,3,5-triphenylbenzene)tris(tricarbonylchromium⁽⁰⁾) 
• 43140-24-5 (1,3,5-triphenylbenzene)bis(tricarbonylchromium⁽⁰⁾) 
• 116172-83-9 tricarbonyl(1,3,5-triphenylbenzene)chromium⁽⁰⁾ 
• 116172-83-9 tricarbonyl(1,3,5-triphenylbenzene)chromium⁽⁰⁾ 
• 151417-38-8 1,3,5-tris(4-iodophenyl)benzene 
• 83313-85-3 1,3,9-triphenyl-9-fluorenol 

Relevant academic research and scientific papers

Efficient conversion of acetophenones into 1,3,5-triarylbenzenes catalyzed by bismuth(III) trifluoromethanesulfonate tetrahydrate

Bismuth(III) trifluoromethanesulfonate tetrahydrate is found to efficiently catalyze the cyclotrimerization of acetophenones into 1,3,5-triarylbenzenes in good yields. Georg Thieme Verlag Stuttgart.

Highly efficient and novel method for synthesis of 1,3,5-triarylbenzenes from acetophenones

Heteropolyacid-phosphomolybdic acid has been found to be an efficient and recyclable catalyst for cyclotrimerization of acetophenones into 1,3,5-triarylbenzenes in good yields.

Thionyl chloride-catalyzed preparation of microporous organic polymers through aldol condensation

We demonstrated the synthesis of five kinds of microporous organic polymers based on aldol self-condensation of di- and multiacetyl-containing building blocks catalyzed by thionyl chloride. The α,β-unsaturated ketone (dimerization) and 1,3,5-trisubstitute

Efficient one-step synthesis of C 3-symmetrical benzenoid compounds mediated by SOCl 2/EtOH

An efficient one-step synthesis of branched functionalized benzenoid compounds from aryl methyl ketones mediated by SOCl2/EtOH is described; some novel C 3-symmetrical molecules were prepared with satisfactory yields. The method enjo

Independent electrocyclization and oxidative chain cleavage along the backbone of cis-poly(phenylacetylene)

cis-Poly(phenylacetylene) (PPA) and cis-poly(pentadeuteriophenylacetylene) (PPA-d5) undergo similar thermally induced transformations in bulk and solution. The structures identified in thermally treated samples include cis - trans isomerization of the backbone, cyclohexadiene repeat units in the main chain, and extruded 1,3,5-triphenylbenzene (1,3,5-C6H 3Ph3). Among these structures, cyclohexadiene sequences along the backbone formed by intramolecular cyclization are the principal products in all solvents regardless of temperature and the presence or absence of ambient light or O2. We propose that cyclohexadiene structures form via 6π electrocyclization of triene sequences and, therefore, are an unavoidable consequence of cis-alkene units of the polyene backbone. Concurrent with cyclization, decrease of molecular weight and increase of molecular weight distribution are observed. Traces of acid lead to a dramatic increase in cyclization. Extrusion of 1,3,5-C6H3Ph3 results from cyclohexadiene repeat units and is slower than electrocyclization, even in the presence of acid, light, or O2. In the presence of ambient light, O2 accelerates the rate of cyclization and extrusion of 1,3,5-C6H3Ph3, the decrease of molecular weight, and the formation of carbonyl-containing products detected in a 5:1 molar ratio to extruded 1,3,5-C6H3Ph3. Under these conditions, the most dramatic changes in molecular weight and molecular weight distribution are observed.

TiCl3(OTf) catalyses the efficient conversion of acetophenones to 1,3,5-triaryl benzenes

The quantitative conversion of different substituted acetophenones to their corresponding 1,3,5-triaryl benzenes was achieved in the presence of catalytic amounts of TiCl3(OTf) in sealed tubes at 90-100°C.

Simple and convenient synthesis of 1,3,5-triarylbenzenes from ketones

A new and efficient synthesis of a series of 1,3,5-triarylbenzenes was accomplished in good yields via the triple condensation of aryl methyl ketones promoted by thionyl chloride in anhydrous ethanol. The method is simple and convenient.

Silver(I) Interactions with Ketones. Site of Complexation with Acetophenones and Effectiveness as a Lewis Acid Catalyst

Aromatic ketones present three possible sites for complexation of Ag(1+): the oxygen lone pair, the ? electrons of the carbonyl bond, and the ? electrons of the aromatic ring.Upfield shifts of (13)C chemical shifts of meta and para carbons of acetophenone in the presence of silver nitrate showed that Ag(1+) complexes with the aromatic ring moiety in water.This contrasts with previous results in methylene chloride in which the carbonyl group is not hydrogen bonded to solvent and acts as an n donor toward Ag(1+).In the solid state, an X-ray structure determination of (p-methylacetophenone)2AgBF4 showed that Ag(1+) was tetracoordinated to two carbonyl oxygens (2.36 Angstroem) and to two aromatic rings of different ketone molecules (2.55- and 2.72-Angstroem distances to meta and ortho carbons, respectively).Thus in the solid state, acetophenone acts both as an n and ? donor.The Ag-O bond was shorter than most Ag-O bonds and appears to contribute more to the stabilization of the complex than Ag(1+) interactions with the benzene rings.An sp2 hybridization at oxygen was indicated by an AgOC angle of 137 deg and the fact that Ag(1+) is only 6.2 deg above the plane of the carbonyl bond.Although Ag(1+) catalyzed an aldol condensation of acetophenone in 1,2-dichloroethane at 70-80 deg C, rates of hydrogen exchange for acetone in deuterated water at 44 deg C showed no catalytic activity of AgNO3 or LiNO3.

OLIGOMERISATION OF PHENYL ACETYLENE OVER TITANIUM OXIDE SUPPORTED ON SILICA - ALUMINA CATALYST

Titanium oxide on silica-alumina support is found to be effective for oligomerisation of phenyl acetylene.Cyclic trimerisation of the acetylene leading to trisubstituted benzene was also found to occur during the oligomerisation, in addition of the formation of small quantities of a ketone by the reaction of phenyl acetylene with moisture over the catalyst surface.

2-cyano-iso-propyl radical addition to alkynes

The thermolysis of azobisisobutyronitrile (AIBN) in benzene in the presence of various mono- and di-substituted acetylenes has been investigated in order to ascertain the chemical reactivity of transient 2-cyano-isopropyl radical (CPR) towards carbon-carbon triple bonds. Results show that this rather sluggish and bulky carbon centered radical successfully adds in a regioselective fashion to alkynes bearing an electron acceptor phenyl, methoxycarbonyl and trimethylsilyl substituent, but fails with alkylacetylenes and those sterically hindered. The produced vinyl radicals undergo H-abstraction reaction, alkyne addition, aromatic addition and intramolecular cyclization in a relative proportion strongly dependent upon the nature of both 1- and 2-substituent. Two unprecedented examples of 4-exo and 6-exo vinyl radical cyclization onto the cyano triple bond are reported.