92-06-8

Usage

Uses

Used in Electronic Equipment Industry:
1,3-Diphenylbenzene is used as a component in electronic equipment due to its chemical stability and heat-transfer properties.
Used in Lubricant Industry:
1,3-Diphenylbenzene is used as a lubricant in various applications, taking advantage of its heat-transfer capabilities and chemical properties.
Used in Sealant Industry:
1,3-Diphenylbenzene is used in sealants to provide a stable and durable seal, leveraging its chemical and physical properties.
Used in Other Devices:
1,3-Diphenylbenzene is also utilized in other devices that require its specific chemical and physical attributes, such as its heat-transfer properties and chemical stability.
Used as a Heat-Transfer Fluid:
1,3-Diphenylbenzene is used as a heat-transfer fluid in various industrial applications, including in the shipping of the solid mixture with its isomers o-terphenyl and p-terphenyl, due to its ability to efficiently transfer heat and its chemical properties.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 3162, 1986 DOI: 10.1021/jo00366a016

Reactivity Profile

1,3-Diphenylbenzene is non-flammable but combustible (flash point 403°F). Extremely stable thermally. Incompatible with strong oxidizing agents but not very reactive at room conditions.

Hazard

Moderately toxic by ingestion. Combustible. Eye and upper respiratory tract irritant.

Purification Methods

Purify it as for o-terphenyl above. [Beilstein 5 IV 2480.]

InChI:InChI=1/C18H14/c1-3-8-15(9-4-1)17-12-7-13-18(14-17)16-10-5-2-6-11-16/h1-14H

Upstream product

• 110-89-4 piperidine 
• 60-29-7 diethyl ether 
• 591-51-5 phenyllithium 
• 2051-62-9 4'-biphenyl chloride 
• 1502-22-3 2-(1-cyclohexenyl)cyclohexanone 
• 92-52-4 biphenyl 
• 2396-01-2 phenyl radical 
• 100-34-5 benzene diazonium chloride 
• 10346-08-4 3,5-diphenylcyclohex-2-en-1-one 
• 108-36-1 1,3-dibromobenzene 
• 84-15-1 o-terphenyl 
• 92-94-4 [1,1';4',1'']terphenyl 
• 24344-21-6 2,6-bis(1-cyclohexenyl)cyclohexanone 
• 1667-08-9 1,3-diphenyl-cyclohexane 

Downstream Products

• 92-94-4 [1,1';4',1'']terphenyl 
• 1706-50-9 perhydro-meta-terphenyl 
• 60631-83-6 4’-Bromo-[1,1’:3’,1”]terphenyl 
• 133476-13-8 benzothieno<2,3-b>dibenzothiophene-3,9-disulfonic acid 5,5,7,7-tetraoxide 
• 15295-65-5 [2,4-bis(phenyl)phenyl]phenylmethanone 
• 6007-94-9 4-biphenyl-3-yl-benzophenone 
• 855276-49-2 4-biphenyl-3-yl-4'-methoxy-benzophenone 
• 90248-30-9 phenyl-m-terphenyl sulfone 
• 34177-25-8 4-iodo-[1,1':3',1]terphenyl 
• 124526-56-3 4,4-dihydroxy-1,1':3',1-terphenyl 
• 133476-14-9 2-(4-chlorosulfonylphenyl)-7-chlorosulfonyldibenzothiophene 5,5-dioxide 
• 716-76-7 3-phenylbenzoic acid 
• 65-85-0 benzoic acid 
• 38113-01-8 1'-Methyl-1',4'-dihydro-m-terphenyl 

Relevant academic research and scientific papers

Single electron transfer reductive cleavage of the aryl-nitrogen bond in phenyl-substituted dimethylanilines

By treatment with Li metal in THF at room temperature the three isomeric N,N-dimethylaminobiphenyls and N,N-dimethyl-2,6-diphenylaniline underwent 100% regioselective reductive cleavage of the aryl-N bond, affording biphenyl and meta-terphenyl, respectively, in various yields.

A straightforward synthesis of 4,5-dihalofunctionalized imidazol-2-ylidene/imidazolyl-metal complexes from trihaloimidazolium salts/imidazoles: Structure and catalytic studies

Backbone dihalofunctionalized imidazol-2-ylidene/imidazolyl-metal complexes (5?13) of group–10 metal ions were synthesized through a proficient and single step oxidative addition method using 2,4,5-trihaloimidazolium salts or imidazoles respectively. The donor property of 4,5-diiodofunctionalized imidazol-2-ylidene was described for the first time. The catalytic activity of palladium complexes containing imidazol-2-ylidene (6 and 7)/imidazolyl (10 and 11) groups towards Suzuki-Miyaura coupling reaction of aryl bromides was evaluated and compared with its unsubstituted counterpart. Besides, the investigation of reaction pathway in catalysis was carried out.

Nickel(II) benzimidazolin-2-ylidene complexes with thioether-functionalized side chains as catalysts for Suzuki-Miyaura cross-coupling

Four bis(benzimidazolin-2-ylidene) nickel(II) complexes featuring thioether moieties in the side chain have been synthesized by reactions of the respective benzimidazolium salts with nickel(II) acetate in molten tetrabutylammonium bromide as an ionic liqu

Suzuki cross-coupling of hexachlorobenzene promoted by the Buchwald ligands

The study of cross-coupling between hexachlorobenzene and phenylboronic acid comprised five Buchwald ligands, from which 2-dicyclohexylphosphino-2′-(dimethylamino)biphenyl (DavePHOS) provided the best conversion. When excess of phenylboronic acid was used, a mixture of isomeric tri-, tetra- and pentaphenyl-substituted derivatives in the ～10:70:20 ratio was obtained, along with minor amounts of hydrodechlorination products.

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).

PRODUCTION METHOD OF COUPLING COMPOUND

PROBLEM TO BE SOLVED: To provide a production method of a coupling compound due to a cross-coupling reaction that uses a novel reaction substrate. SOLUTION: A production method of a coupling compound characterized by producing a compound (C) from a compound (A) and a compound (B) according to a coupling reaction represented by the following formula (1). As a reaction substrate of a cross-coupling reaction, by using a compound having a -SF5 group, which is excellent in safety and has no problem of toxicity of a byproduct, various kinds of coupling compounds may be produced at a high yield. (In the formula (1), R1 and R2 represent independently an arbitrary monovalent atomic group, Z represents a leaving group, and M represents a transition metal catalyst.) SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Tris-NHC-propagated self-supported polymer-based Pd catalysts for heterogeneous C-H functionalization

Three-dimensionally propagated imidazolium-containing mesoporous coordination polymer and organic polymer-based platforms were successfully exploited to develop single-site heterogenized Pd-NHC catalysts for oxidative arene/heteroarene C-H functionalization reactions. The catalysts were efficient in directed arene halogenation, and nondirected arene and heteroarene arylation reactions. High catalytic activity, excellent heterogeneity and recyclability were offered by these systems making them promising candidates in the area of heterogeneous C-H functionalization, where efficient catalysts are still scarce.

New Nickel-Based Catalytic System with Pincer Pyrrole-Functionalized N-Heterocyclic Carbene as Ligand for Suzuki-Miyaura Cross-Coupling Reactions

A new catalytic system with Ni(NO3)2·6H2O as the catalyst and a pincer pyrrole-functionalized N-heterocyclic carbene as the ligand was employed in the Suzuki-Miyaura cross-coupling reactions of aryl iodides with arylboronic acids. With 5 mol% catalyst, the catalytic reactions proceeded at 160 °C, giving coupling products in isolated yields of up to 94% in short reaction times (1-4 h). The system worked efficiently with aryl iodides bearing electron-donating or electron-withdrawing groups and arylboronic acids with electron-donating groups. Steric effects were observed for both aryl iodides and arylboronic acids. It is proposed that the reactions underwent a Ni(I)/Ni(III) catalytic cycle.

Copper-catalyzed meta-selective arylation of phenol derivatives: An easy access to m-aryl phenols

Achieving selective meta-functionalization of phenols is a significant challenge. Accessing such compounds generally needs elevated temperature or incorporation of complex templates. Here, we report a general approach to achieve meta-arylated phenols with a simple and common directing group. This coppercatalyzed protocol proceeds with complete meta-selectivity and tolerates a variety of functional groups in both coupling partners. Computational studies have revealed that the reaction proceeded via a Heck-like pathway.

Palladium (II)–Salan Complexes as Catalysts for Suzuki–Miyaura C–C Cross-Coupling in Water and Air. Effect of the Various Bridging Units within the Diamine Moieties on the Catalytic Performance

Water-soluble salan ligands were synthesized by hydrogenation and subsequent sulfonation of salens (N,N’-bis(slicylidene)ethylenediamine and analogues) with various bridging units (linkers) connecting the nitrogen atoms. Pd (II) complexes were obtained in reactions of sulfosalans and [PdCl4]2?. Characterization of the ligands and complexes included extensive X-ray diffraction studies, too. The Pd (II) complexes proved highly active catalysts of the Suzuki–Miyaura reaction of aryl halides and arylboronic acid derivatives at 80 ?C in water and air. A comparative study of the Pd (II)–sulfosalan catalysts showed that the catalytic activity largely increased with increasing linker length and with increasing steric congestion around the N donor atoms of the ligands; the highest specific activity was 40,000 (mol substrate) (mol catalyst × h)?1. The substrate scope was explored with the use of the two most active catalysts, containing 1,4-butylene and 1,2-diphenylethylene linkers, respectively.