17057-88-4

Basic information

• Product Name: 3,5-DIMETHYL-BIPHENYL
• Synonyms: 3,5-DIMETHYL-BIPHENYL;3,5-dimethyl-1,1'-biphenyl;Einecs 241-120-5
• CAS NO: 17057-88-4
• Molecular Formula: C₁₄H₁₄
• Molecular Weight: 182.26096
• EINECS: 241-120-5
• Mol File: 17057-88-4.mol
• Article Data: 165

Chemical Properties

• Melting Point: 22.5°C
• Boiling Point: 278.85°C
• Flash Point: 121.6°C
• Appearance: /
• Density: 0.9990
• Refractive Index: 1.5952
• CAS DataBase Reference: 3,5-DIMETHYL-BIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIMETHYL-BIPHENYL(17057-88-4)
• EPA Substance Registry System: 3,5-DIMETHYL-BIPHENYL(17057-88-4)

Safety Data

• Hazardous Substances Data: 17057-88-4(Hazardous Substances Data)

Usage

Uses

3,5-Dimethyl-biphenyl is a useful reagent for organic synthesis. It is used in the preparation of orthopalladated complexes with multidentated ligands as catalyst for Suzuki and heck reactions.

Upstream product

• 926-54-5 trans-2-methyl-1,3-pentadiene 
• 536-74-3 phenylacetylene 
• 172975-69-8 3,5-dimethylphenyl boronic acid 
• 2996-92-1 phenyl trimethylsiloxane 
• 106-42-3 para-xylene 
• 71-43-2 benzene 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 98-86-2 acetophenone 
• 940-93-2 2,4,6-trimethylpyrylium chlorate(VII) 
• 33586-45-7 1-Phenyl-3,5-dimethyl-cyclohexen-1 
• 108-90-7 chlorobenzene 
• 556-97-8 1-chloro-3,5-dimethylbenzene 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 100-63-0 phenylhydrazine 

Downstream Products

• 787576-85-6 (2,6-dibromo-4-phenylphenyl)(2,6-dimethyl-4-phenylphenyl)chloromethane 
• 787576-75-4 (2,6-dibromo-4-phenylphenyl)(2,6-dimethyl-4-phenylphenyl)methanol 
• 787576-73-2 {(2,6-bibromo-4-phenyl)phenyl}{(2,6-dimethyl-4-phenyl)phenyl}ketone 
• 787576-61-8 (2,6-dibromo-4-phenylphenyl)(2,6-dimethyl-4-phenylphenyl)diazomethane 
• 787576-86-7 ethyl N-(2,6-dibromo-4-phenylphenyl)(2,6-dimethyl-4-phenylphenyl)methylcarbamate 
• 787576-87-8 ethyl N-nitroso-N-(2,6-dibromo-4-phenylphenyl)(2,6-dimethyl-4-phenylphenyl)methylcarbamate 
• 787576-62-9 (2,4,6-triphenylphenyl)(2,6-dimethyl-4-phenylphenyl)diazomethane 
• 787576-78-7 [2,6-bis{2-fluorophenyl}-4-phenylphenyl](2,6-dimethyl-4-phenylphenyl)diazomethane 
• 787576-83-4 ethyl N-nitroso-N-(2,4,6-triphenylphenyl)(2,6-dimethyl-4-phenylphenyl)methylcarbamate 
• 787576-88-9 ethyl N-(2,4,6-triphenylphenyl)(2,6-dimethyl-4-phenylphenyl)methylcarbamate 
• 787576-80-1 ethyl N-[2,6-bis(2-fluorophenyl)-4-phenylphenyl](2,6-dimethyl-4-phenylphenyl)methylcarbamate 
• 787576-82-3 [{2,6-di(phenyl-d5)-4-phenyl}phenyl](2,6-dimethyl-4-phenylphenyl)diazomethane 
• 787576-63-0 [2,6-bis{3,5-bis(trifluoromethyl)phenyl}-4-phenylphenyl](2,6-dimethyl-4-phenylphenyl)diazomethane 
• 853774-74-0 ethyl N-[{2,6-di(phenyl-d5)-4-phenyl}phenyl](2,6-dimethyl-4-phenylphenyl)methylcarbamate 

Relevant articles and documents

Ligand-promoted oxidative cross-coupling of aryl boronic acids and aryl silanes by palladium catalysis

The first cross-coupling reaction between aryl silanes and aryl boronic acids is described. This transformation represents one of the very few examples of coupling reactions between two nucleophilic organometallic reagents and provides a new method for the formation of biaryl compounds. The successful development of this reaction was enabled by the use of commercially available 2,2-bis(diphenylphosphino)-1,1-binaphthyl (BINAP) as the ligand. A small amount of BINAP (3 mol %) was sufficient to suppress the formation of the homocoupling products, and the reaction yielded the cross-coupling products with high selectivity under mild conditions, even when the ratio of the two coupling partners was 1:1.

PH-Induced Linkage Isomerism of Pd(II) Complexes: A Pathway to Air- and Water-Stable Suzuki-Miyaura-Reaction Catalysts

The Pd(II) complexes of the ambidentate pyridyldiketones 2,2-dimethyl-5-(3- or 4-pyridyl)pentane-3,5-dione are readily prepared in their linkage isomeric forms by the appropriate pH control during syntheses. The isolated diketonate- or pyridine-bound species can be interconverted with essentially 100% efficiency by treatment with an acid or base, respectively. Under the normal basic conditions for a Suzuki-Miyaura coupling, only the diketonate forms are present and act as very efficient catalysts for this reaction. The dynamic nature of the presented complexes allows the catalytic process to be quenched and reactivated at any stage without the risk of losing the catalyst's activity.

A novel P,S-heterodonor ligand and palladium(0) complex catalyzed Suzuki cross-coupling reaction

In the presence of a novel P,S-heterodonor ligand, palladium(0)-catalyzed Suzuki cross-coupling reaction proceeded smoothly at 80°C in DMSO. Axially dissymmetric P,S-heterodonor ligand L3 synthesized from BINOL is an effective promoter in the palladium(0)-catalyzed Suzuki cross-coupling reaction of phenylboronic acid with aryl bromides and iodide at 60-80°C. On the basis of 13C and 31P NMR spectroscopic investigation and X-ray diffraction, it was revealed that N,N-dimethylthiocarbamate-phosphine ligand L3 might be a P,S-heterodonor bidentate ligand to palladium(0) center.

Porous Organic Phenanthroline-Based Polymer as an Efficient Transition-Metal-Free Heterogeneous Catalyst for Direct Aromatic C?H Activation

Direct C?H bond transformation has been regarded as one of the most important areas in organic synthesis in both academia and industry. However, the heterogeneous transition-metal-free catalysis of direct C?H bond transformation has remained a contemporary challenge. To tackle this challenge, we designed and constructed a porous phenanthroline-based polymer (namely POP-Phen) via free radical polymerization of vinyl-functionalized phenanthroline monomers. POP-Phen shows excellent catalytic performances in transition-metal-free catalyzed C?H arylation, even better than those of the corresponding homogeneous catalyst, which is mainly attributed to the high density of catalytically active sites in the heterogeneous catalyst. Kinetic isotope experiments and spectral characterizations demonstrate the electron-transfer between the heterogeneous catalyst and the base (t-BuOK), a key step for C?H activation. We believe that this porous organic phenanthroline polymer could open a new door for the design of novel heterogeneous transition-metal-free catalysts for direct C?H activation.

Hydrodefluorinations of trifluorotoluenes by LiAlH4 and TiCl4

In the presence of 2 mol% of TiCl4, α,α,α- trifluorotoluene derivatives were reduced with LiAlH4 to furnish toluene derivatives in high yields. Selective reduction of bis(trifluoromethyl) benzene derivative is effected. The difference of the reactivity between TiCl4 and NbCl5 is also discussed.

Photoaccelerated energy transfer catalysis of the Suzuki-Miyaura coupling through ligand regulation on Ir(iii)-Pd(ii) bimetallic complexes

Three bimetallic Ir(iii)-Pd(ii) complexes [Ir(ppy)2(bpm)PdCl2](PF6) (ppy = 2-phenylpyridine, 1), [Ir(dfppy)2(bpm)PdCl2](PF6) (dfppy = (4,6-difluorophenyl)pyridine, 2), and [Ir(pq)2(bpm)PdCl2](PF6) (pq = 2-phenylquinoline, 3) were synthesized by using 2,2′-bipyrimidine (bpm) as a bridging ligand. The influences of the cyclometalated ligand at the Ir(iii) center on the photophysical and electrochemical properties as well as photocatalytic activity for the Suzuki-Miyaura coupling reaction under mild conditions were evaluated. The results revealed that complex 3 enables dramatically accelerating the Suzuki-Miyaura coupling reaction under visible light irradiation at room temperature, due to the effective absorption of visible light and appropriate locus of the excited chromophore. Mechanism studies showed that the chromophore [Ir(pq)2(bpm)] fragment absorbs visible light to produce the triplet excited state centering on the bridging ligand which boosts the formation of electron rich Pd(ii) units and facilitates the oxidative addition step of the catalytic cycle. Simultaneously, the excited chromophore undergoes energy transfer efficiently to the Pd(ii) reaction site to form the excited Pd(ii) species, resulting in enhancement of Pd(ii) reduction steps of the Suzuki-Miyaura coupling reaction and increasing the reactivity of the catalyst. This provides a new strategy for designing photocatalysts for coupling reaction through altering the cyclometalated ligand to modulate the photophysical properties and the cooperation between two metal units.

An efficient Stille cross-coupling reaction catalyzed by Pd(OAc) 2/DAB-Cy catalytic system

An efficient palladium-catalyzed Stille cross-coupling reaction has been developed. In the presence of 3 mol% of Pd(dba)2 and 6 mol% of DAB-Cy (1,4-dicyclohexyl-diazabutadiene), various aryl halides (iodides and bromides) were coupled with organotin compounds to afford the corresponding biaryls and alkyne in good to excellent yields. Furthermore, high TONs [turnover numbers, TONs up to 950,000 for the reaction of 1-iodo-4-nitrobenzene and tributyl(phenyl)stannane] for the Stille cross-coupling reaction were observed.

Dendrimer-encapsulated Pd nanoparticles as catalysts for C-C cross-couplings in flow microreactors

The inner walls of glass microreactors were functionalized with dendrimer-encapsulated Pd nanoparticles. The catalysts were efficient for the Heck-Cassar (copper-free Sonogashira) and Suzuki-Miyaura (SMC) cross-coupling reactions. For the Heck-Cassar reaction between iodobenzene and phenylacetylene, the catalytic system exhibited a high turnover frequency (TOF) and on average required milder reaction conditions as compared to other continuous flow cross-couplings. A study of the substituent effect of para-substituted aryl halides revealed a beneficial effect of electron-withdrawing side groups for the SMC. Moreover, a reaction constant (ρ) of 1.5, determined from the Hammett plot, indicated a possible rate-determining step other than the oxidative addition.

Suzuki-Miyaura cross-couplings of arenediazonium tetrafluoroborate salts with arylboronic acids catalyzed by aluminium hydroxide-supported palladium nanoparticles

Suzuki-Miyaura cross-couplings of arenediazonium salts with arylboronic acids catalyzed by highly active aluminium hydroxide-supported palladium nanoparticles catalyst have been investigated for the first time. The reactions are performed at 25 °C in MeOH without any base and ligand to afford biaryls in good to excellent yields under non-anhydrous and non-degassed conditions.

Improved procedure for palladium-catalyzed Hiyama cross-coupling reaction of aryl halides with aryltrimethoxysilanes under solvent-free conditions

An improved palladium-catalyzed Hiyama cross-coupling reaction is reported. In the presence of PdCl2(MeCN)2, P(o-tol)3 and TBAF, a number of ArX (X = I, Br, Cl) were coupled with ArSi(OMe)3 efficiently to afford the desired cross-coupled products in moderate to excellent yields. It is noteworthy that this protocol is conducted under relatively low Pd loadings and solvent-free conditions. Georg Thieme Verlag Stuttgart.

Photocatalytic Suzuki coupling reaction using conjugated microporous polymer with immobilized palladium nanoparticles under visible light

Extensive research has been done to develop heterogeneous Pd catalysts for Suzuki coupling reactions, such as the immobilization or stabilization of Pd nanoparticles (NP) on silica, carbon nanotubes, polymers, metal oxides, dendrimers, and graphene layers. Upon photoirradiation, both the average energy and the effective flow of free electrons toward the Pd NPs would be amplified, which can be exploited and harvested to catalyze reactions. Suzuki coupling reactions are performed under homogeneous conditions using a variety of phosphine ligand or palladium catalytic complexes. Despite the relatively high efficiency of these homogeneous systems, the recovery of the costly and potentially toxic palladium catalysts remains as a pressing issue in the development toward a greener, more sustainable chemical industry.

Charge Neutral [Cu2L2] and [Pd2L2] Metallocycles: Self-Assembly, Aggregation, and Catalysis

A range of morphologically distinct metallosupramolecular Cu(II) and Pd(II) complexes has been constructed, based on the tritopic ligand 1,1′,1″-(benzene-1,3,5-triyl)tris(4,4-dimethylpentane-1,3-dione) (H3L). By control of the reaction conditions, it is possible to generate distinct coordination assemblies possessing either macrocyclic or polymeric structures and more importantly distinct activity in catalysis of the Suzuki-Miyaura cross-coupling.

Cage-templated synthesis of highly stable palladium nanoparticles and their catalytic activities in Suzuki-Miyaura coupling

We report the controlled synthesis of small palladium nanoparticles (PdNPs) with narrow particle size distribution (1.8 ± 0.2 nm) using an organic molecular cage as a template. The well-defined cage structure and thioether anchoring groups inside the cavity are critical for the formation of narrowly distributed PdNPs, offering a confined organic molecular environment and guiding PdNP nucleation and growth. The resulting encapsulated PdNPs are resistant to agglomeration and stable in solution exposed to air at room temperature. When provided with a protective cage shell with minimum surface coverage, such PdNPs are capable of catalyzing organic reactions, showing high catalytic activity in Suzuki-Miyaura coupling reactions.

An efficient Pd/Al(OH)3 nanoparticle catalyst for Suzuki coupling reactions of aryl halides

A high-performance palladium-based Pd/Al(OH)3 catalyst has been prepared by the one-pot three-component method. It was found that this 'ligandless' Pd/Al(OH)3 catalyst showed remarkable reactivity and gave excellent yields (up to 99%) towards the condensation of aryl bromides with various arylboronic acids under mild conditions, and afforded good yields of the coupling products (up to 97%) with most aryl chlorides in two different catalytic systems. Furthermore, this catalyst could be easily recovered through filtration and reused for 8 cycles without significant loss of the yield.

Pd(0)/Au(i) redox incompatibilities as revealed by Pd-catalyzed homo-coupling of arylgold(i)-complexes

A Pd(ii)-catalyzed homo-coupling of Au(i)-aryls is reported. The reaction is driven by a Pd(0)/Au(i) redox reaction that generates a gold mirror and Pd(ii), and illustrates one of the challenges for developing dual catalytic Au-Pd systems.

Palladium-catalyzed Suzuki cross-couplings of N′-mesyl arylhydrazines via C-N bond cleavage

An efficient palladium-catalyzed Suzuki cross-coupling reaction of N′-mesyl arylhydrazine with aryl boronic acid is described, which affords the corresponding biaryl compounds in high yields. This transformation proceeds through C-N bond cleavage under mi

CuI/DABCO-catalyzed cross-coupling reactions of aryl halides with arylboronic acids

CuI combined with DABCO (1,4-diaza-bicyclo[2.2.2]octane) was developed as an inexpensive and efficient catalytic system for the Suzuki-Miyaura cross-coupling of aryl halides with arylboronic acids. The couplings between aryl iodides and arylboronic acids catalyzed by catalytic amounts of CuI and DABCO proceeded smoothly in moderate to excellent yields. However, the CuI/DABCO system was less efficient in the reactions of aryl bromides, and a higher reaction temperature was required to improve the yield. For the less activated aryl bromides, a stoichiometric amount of CuI together with TBAB was necessary to obtain satisfactory yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Organocatalytic synthesis of (Het)biaryl scaffoldsviaphotoinduced intra/intermolecular C(sp2)-H arylation by 2-pyridone derivatives

A uniqueN,O-bidentate ligand 6-oxo-1,6-dihydro-pyridone-2-carboxylic acid dimethylamide (L1) catalyzed direct C(sp2)-H (intra/intermolecular) arylation of unactivated arenes has been developed to expedite access to (Het)biaryl scaffolds under UV-irradiation at room temperature. The protocol tolerated diverse functional groups and substitution patterns, affording the target products in moderate to excellent yields. Mechanistic investigations were also carried out to better understand the reaction pathway. Furthermore, the synthetic applicability of this unified approach has been showcasedviathe construction of biologically relevant 4-quinolone, tricyclic lactam and sultam derivatives.

Lipids as versatile solvents for chemical synthesis

Development of safe, renewable, cheap and versatile solvents is a longstanding challenge in chemistry. We show here that vegetable oils and related systems can become prominent solvents for organic synthesis. Suzuki-Miyaura, Hiyama, Stille, Sonogashira and Heck cross-couplings proceed with quantitative yields in a range of vegetable oils, fish oil, butter and waxes used as solvents. Appropriate methodologies for high-throughput screening and sustainable isolation techniques applicable for vegetable oils and related lipids are presented.