3383-32-2

Usage

Structure

Tetrasubstituted benzene with four phenyl groups attached to different positions (1, 2, 4, and 5) on the benzene ring

Physical state

White crystalline solid

Solubility

Insoluble in water, soluble in organic solvents

Organic synthesis

Building block for the synthesis of larger organic molecules

Materials science

Component in the production of organic light-emitting diodes (OLEDs) and other electronic devices

Research and industrial value

Unique structure and properties make it a valuable tool for chemical research and industrial applications

Upstream product

• 13074-99-2 1,2,4,5-tetrachloro-3,6-dibromobenzene 
• 31604-30-5 1,2,4,5-tetrabromo-3,6-dichlorobenzene 
• 64-19-7 acetic acid 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 886-38-4 diphenylcyclopropenone 
• 95-94-3 1,2,4,5-tetrachlorobenzene 
• 98-80-6 phenylboronic acid 
• 501-65-5 diphenyl acetylene 
• 100-58-3 phenylmagnesium bromide 
• 591-50-4 iodobenzene 
• 536-74-3 phenylacetylene 

Downstream Products

• 97084-94-1 1,2,4,5-tetracyclohexylbenzene 

Relevant academic research and scientific papers

?-OLEFIN-IRIDIUM KOMPLEXE. X. EINSCHIEBUNG VON DIPHENYLACETYLEN IN DIE METHYLEN-IRIDIUM-BINDUNG VON BIS(η4-CYCLOOCTADIEN-μ-METHYLENE-IRIDIUM)

Bis(η4-cyclooctadiene-μ-methyleneiridium) reacts with acetylenes to yield various products.In the case of diphenylacetylene two compounds have been isolated from the reaction mixture and identified as a 1/1 adduct containing a μ-η1, η3-1,2-diphenylallyl ligand (X-ray structure analysis), and as 1,2,4,5-tetraphenylbenzene.

Buchwald ligand-assisted Suzuki cross-coupling of polychlorobenzenes

Screening of four Buchwald ligands for the cross-coupling of isomeric di-, tri- and tetrachlorobenzenes with arylboronic acids revealed that good yields of exhaustive substitution can be best provided by 2-dicyclohexylphosphino-2′-(dimethylamino) biphenyl (DavePHOS).

Selective and general exhaustive cross-coupling of di-chloroarenes with a deficit of nucleophiles mediated by a Pd-NHC complex

We report the first example of a general, exhaustive Pd-mediated cross-coupling of polychloroarenes in the presence of a deficit of nucleophiles, mediated by the highly active PEPPSI-IPent catalyst. Our results indicate that this catalyst system may be applicable to the pseudo-living polymerisation of chloroarene monomers.

Cross-coupling of polychlorobenzenes with phenylboronic acid in the presence of [Pd]-imidazolium salts as catalytic systems

The reactions of di-, tetra-, and hexachlorobenzenes with phenylboronic acid in the presence of [Pd]-imidazolium salt-base as catalytic systems afford cross-coupling products in moderate yields. The highest conversions are attained when imidazolium salts bearing bulky aromatic substituents are used and the reaction is carried out in the presence of alkali alkoxides containing H α atoms. Cross-coupling is accompanied by hydrodechlorination of aromatic C-Cl bonds.

Zinc-promoted reactions. 6. The reduction of diphenylcyclopropenone in acidic media

The reduction of diphenylcyclopropenone with zinc was investigated under a variety of conditions. The product distribution can be explained in terms of a general mechanism for zinc-promoted reductions.

ZINC-PROMOTED REACTIONS. III. THE REDUCTION OF α,β-UNSATURATED KETONES IN ACETIC ACID

The zinc-promoted reduction of 1,3-diphenylpropenone, 1, 4-phenyl-3-buten-2-one, 2, and 3-penten-2-one, 3, have been reinvestigated in AcOH.The reduction of 1 in neat AcOH gave 1,3-diphenylpropene, 4, 1,3-diphenylpropan-1-ol, 5, 1,3-diphenylpropane, 6, and 1,3,4,6-tetraphenylhexane-1,6-dione, 12, in comparable yields, accounting for about 90percent of the product.In the presence of co-reagents like LiCl, HCl, and CF3CO2H, the predominant products was 4, and a more scattered product distribution was observed.In addition to compounds 4-6, and 12, 1-acetoxy-1,2-diphenylcyclopropane, 1,2-diphenylcyclopropene, 1,2,4,5-tetraphenylbenzene, and two dimeric polyenes were formed in minor amounts.Instead, the reduction of 2 gave ketonic compounds only, 4-phenylbutan-2-one, being the predominant product in all the reactions performed in anhydrous AcOH.Under the classical Clemmensen procedure, i.e. in 7 M HCl, the reductions of 1 and 2 were diverted towards the formation of dimeric ketones.The reduction of 3 resulted exclusively in the saturation of the double bond.The mechanisms possibly involved and, in particular, the chemoselective reduction of the carbon-carbon double bond, are discussed.

Reaction of Aryl Grignard Reagents with Hexahalobenzenes: Novel Arenes via a Multiple Aryne Sequence

New methodology for forming four to six new carbon-carbon bonds to an existing benzene ring in a "one-pot" reaction is described.Reaction of hexabromobenzene (7) or 1,2,4,5-tetrabromo-3,6-dichlorobenzene with excess arylmagnesium bromide in THF gives, after aqueous quench, 1,2,4,5-tetraarylbenzenes in good yield (Table I).The actual product is the corresponding di-Grignard 29, formed from a tetrahalo di-Grignard (24, 31) through a sequence of organometallic aryne intermediates (Scheme II).