612-75-9

Usage

Uses

Used in Chemical Synthesis:
3,3'-Dimethylbiphenyl is used as a reagent in the Pd-catalyzed chemoselective arylation of functionalized 4-chlorocoumarins with triarylbismuth. This application is particularly relevant in the field of organic chemistry, where the compound serves as a key intermediate in the synthesis of various complex molecules and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,3'-Dimethylbiphenyl is used as a building block for the development of new drugs and medicinal compounds. Its unique structure and chemical properties make it a valuable component in the design and synthesis of novel therapeutic agents.
Used in Material Science:
3,3'-Dimethylbiphenyl is also utilized in the field of material science, where it can be employed in the development of advanced materials with specific properties, such as improved thermal stability, electrical conductivity, or mechanical strength.
Used in Research and Development:
Due to its unique chemical structure and properties, 3,3'-Dimethylbiphenyl is often used in research and development settings to explore new reaction pathways, study the effects of structural modifications on chemical behavior, and develop new synthetic methodologies.

Synthesis Reference(s)

Tetrahedron, 26, p. 4041, 1970 DOI: 10.1016/S0040-4020(01)93044-3

Upstream product

• 591-17-3 meta-bromotoluene 
• 625-95-6 3-Iodotoluene 
• 1611-92-3 3,5-dibromotoluene 
• 612-84-0 2,2'-dimethyl-4,4'-biphenol 
• 119-93-7 o-tolidin 
• 20333-41-9 bis(3-methylphenyl)disulfide 
• 10325-82-3 m-tolyllithium 
• 28987-79-3 m-tolylmagnesium bromide 
• 636-98-6 p-nitrobenzene iodide 
• 937-01-9 trimethyl(3-methylphenyl)stannane 
• 108-86-1 bromobenzene 
• 121905-60-0 3-methylphenylmagnesium chloride 
• 1207-15-4 2,8-dimethyldibenzothiophene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 24656-53-9 3,3'-bis(bromomethyl)biphenyl 
• 61794-96-5 4,4'-dibromo-3,3'-dimethyl-1,1'-biphenyl 
• 7583-27-9 4,4'-diiodo-3,3'-dimethylbiphenyl 
• 132657-07-9 3,6,6-Trimethoxy-1-methyl-3-(3-methylphenyl)cyclohexa-1,4-diene 
• 132657-08-0 3,6,6-Trimethoxy-3-methyl-1-(3-methylphenyl)cyclohexa-1,4-diene 
• 1217-45-4 9,10-dicyanoanthracene radical anion 
• 80721-78-4 2,6,9,10-tetracyanoanthracene radical anion 
• 24656-54-0 <2₂>(3,3')biphenylophane 
• 121-91-5 isophthalic acid 
• 158619-46-6 3-(3-Methylphenyl)benzoic acid 
• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 
• 7383-90-6 3,4'-dimethylbiphenyl 
• 4575-13-7 2,3,3′,3′′′-tetramethyl-1,1′:4′1:4,1′′′-quaterphenyl 
• 7583-28-0 4,4'''-Diethynyl-3,2',2'',3'''-tetramethyl-[1,4';1',1'';4'',1''']quaterphenyl 

Relevant academic research and scientific papers

Hydrodesulfurization of 4,6-DMDBT in the high boiling fraction of gas oil

A high boiling fraction of straight run gas oil, which contained 4,6-DMDBT by addition but free from dimethylbiphenyl and dimethylcyclohexylbenzene of its HDS products, was desulfurized over commercial catalysts to find principal products of 4,6-DMDBT. Thus, HDS of 4,6-DMDBT in the high boiling fraction of real feed was proved to proceed principally through hydrogenative route. During the HDS of the fraction, 4,6-DMDBT was found to be produced from trimethyldibenzothiophenes. This activity depended very much on the acidity of the catalyst.

Palladium effect over Mo and NiMo/alumina-titania sulfided catalysts on the hydrodesulfurization of 4,6-dimethyldibenzothiophene

The influence of Pd as additive for Ni and Mo catalysts supported on alumina-titania (Mo/AT) sulfided catalysts was investigated in the hydrodesulfurization of 4,6-dimethyldibenzothiophene. Pd incorporation was carried out in the oxidic phases by using sequential impregnation. The alumina-titania support was formed by anatase-TiO2 crystallites randomly dispersed on γ-Al2O3. Characterization by X-ray diffraction and Raman spectroscopy revealed that MoOx species for PdMo supported on alumina-titania displayed larger particles than those in PdNiMo catalysts. HRTEM images showed an increase in order and stacking for MoS 2 slabs after Pd addition to NiMo samples, as compared with Mo/AT. Pd incorporation over the NiMo/AT sample increased the reaction rate by 30% while no significant increase was recorded for the PdMo sample. This value corresponds to the most active catalyst and it points out to a promoting effect by Pd. This prominent hydrodesulfurization capacity for the PdNiMo/AT suggests a close interaction of Pd with NiMo. Furthermore, since Pd promoted the HDS activity for a NiMo system, the alumina-titania support played an important role.

Noble metal silicides catalysts with high stability for hydrodesulfurization of dibenzothiophenes

Development of highly efficient and long stable hydrodesulfurization (HDS) catalysts still is a great challenge for the refining industry. In this work, a series of intermetallic noble metal silicides supported by carbon nanotubes catalysts (Pt2Si/CNTs, RhxSi/CNTs, and RuSi/CNTs) have been developed by chemical vapor deposition successfully, using dichlorodimethylsilane as Si source. These materials were used as efficient catalysts for the deep HDS of dibenzothiophenes (4,6-DMDBT and DBT) and performed high selectivity to the direct desulfurization pathway. The sequence of HDS activity over noble metal silicides catalysts is in keeping with the sequence of HDS activity of the corresponding metal catalysts, which is Pt2Si/CNTs > RhxSi/CNTs >> RuSi/CNTs. In addition, the Pt2Si/CNTs performed an excellent stability in 100 h stability testing for HDS of 4,6-DMDBT. Therefore, this sulfur-tolerant noble metal silicides could be as promising catalysts for the ultra-deep HDS of fossil-fuel.

Isomerization of substituted biphenyls by superacid. A remarkable confluence of experiment and theory

Acid-catalyzed isomerization of dimethylbiphenyls is determined by the relative stability of intermediate carbocations, rather than the neutral products, and may be predicted by a simple semiempirical method (AM1). A general kinetic model for such isomeri

Mechanism of reaction of trans-diarylbis(diethylphenylphosphine)palladium(II) complexes with aryl iodides to give biaryls

The mechanism of reaction of trans-PdAr2L2 (Ar = m-tolyl or phenyl, L = PEt2Ph) with aryl iodides affording biaryls has been studied.The rate of reaction is independent of the concentration of aryl iodide but is significantly accelerated by the presence of trans-PdAr(I)L2.Cross-over experiments on the reaction of diarylpalladium complexes with monoarylpalladium iodides reveals the occurrence of two types of intermolecular processes between the diaryl and monoaryl complexes.The first process results in a scrambling of aryl groups between the diaryl and monoaryl complexes without formation of biaryls, while the second yields the reductive elimination products, biaryls.

Hydrodesulfurization of 4,6-dimethyldibenzothiophene over promoted (Ni,P) alumina-supported molybdenum carbide catalysts: Activity and characterization of active sites

The effect of phosphorus and nickel on alumina-supported molybdenum oxycarbides has been studied. Catalysts were characterized by elemental analysis, X-ray diffraction, CO chemisorption, transmission electron microscopy, energy-dispersive spectroscopy, X-ray photoelectron spectroscopy, and infrared spectroscopy. Propene and tetralin hydrogenation was used to probe the activity of the doped materials. Hydrodesulfurization of 4,6-dimethyldibenzothiophene (613 K and 4 MPa total pressure) was investigated as a probe for the deep HDS of diesel fuel. For contact times ranging from 0 to 0.4 s (conversion 4+ abundance, increase in the number of Lewis acid sites, and consequent enhancement of the DDS rate. Nickel induces the highest HDS activity; a nickel-molybdenum interaction observed by FTIR spectroscopy of adsorbed CO could be responsible for this behavior.

Activity of Mo(W)S2/SBA-15 Catalysts Synthesized from SiMoW Heteropoly Acids in 4,6-Dimethyldibenzothiophene Hydrodesulfurization

Abstract: Mo(W)/SBA-15 catalysts are prepared using heteropoly acids H4SiMo12O40, H4SiW12O40, and H4SiMo3W9O40. The catalysts in the sulfide form are studied by low-temperature nitrogen adsorption, high-resolution transmission electron microscopy, and X-ray photoelectron spectroscopy. Catalytic properties are tested in the hydrodesulfurization of 4,6-dimethyldibenzothiophene. It is shown that the gas-phase sulfiding of Mo(W)/SBA-15 catalysts leads to increase in the average length of particles and the number of Mo(W)S2 layers in active phase particles compared with liquid-phase sulfiding with the use of dimethyl sulfide. The replacement of a quarter of tungsten atoms with molybdenum ones makes it possible to considerably improve the catalytic activity of the mixed catalyst Mo + W/SBA-15 compared with the monometallic counterparts. This effect can be enhanced due to the use of mixed heteropoly acid H4SiMo3W9O40 as a precursor of the active phase of the MoW/SBA-15 catalyst, which is apparently associated with the formation of MoWS2 active sites.

Investigation of 4,6-dimethyldibenzothiophene hydrodesulfurization over a highly active bulk MoS2 catalyst

The hydrodesulfurization (HDS) of 4,6-dimethyldibenzothiophene was investigated in a batch-stirred microautoclave reactor over a laboratory-synthesized MoS2 catalyst. The reaction was found to proceed through two main parallel pathways: direct desulfurization (DDS) and hydrogenation (HYD). The effect of a wide range of H2S concentrations on the HDS activity and selectivity was studied. Contrary to the well-known inhibition of HDS caused by H2S, the global catalytic activity of HDS was enhanced more than two times with inclusion of H2S in the reaction zone. The increase in the activity is attributed to a significant enhancement in the hydrogenation reaction route, while the direct desulfurization products were only slightly affected. It is suggested that H2S modifies the active sites so that they can be exploited more efficiently in the hydrogenation reaction.

Visible Light Induced Aerobic Coupling of Arylboronic Acids Promoted by Hydrazone

A visible-light-induced oxidative coupling of arylboronic acids has been developed for the synthesis of biaryls. The reaction that employs polydentate hydrazones as the bifunctional catalyst works smoothly under room temperature. It is compatible with a w

Ligand and Base Free Synthesis of Biaryls from Aryl Halides in Aqueous Media with Recyclable Ti0.97Pd0.03O1.97 Catalyst

Abstract: Facile protocol for the synthesis of biaryls from aryl halides in presence of magnesium metal without prior formation of organometallic intermediate has been exploited. Irrespective of aqueous medium, Ti0.97Pd0.03O1.97 catalyst supports C–C bond formation reaction in presence of metals rather than dehalogenation without any additives. Homocoupling of 16 different aryl halides furnished corresponding biphenyls in good yield with better functional group tolerance. The recovery of the catalyst was carried out by employing catalyst coated cordierite monolith up to 7th cycle with high yields. A new approach for the cross-coupling reaction is also attempted. Graphic Abstract: [Figure not available: see fulltext.]