Production Method 1

98-80-6

108-36-1

92-06-8

Reaction Conditions

1.1 Reagents: Tripotassium phosphate ,  Oxygen Catalysts: (SP-4-3)-[2,6-Bis[(di-1-piperidinylphosphino-κP)amino]phenyl-κC]chloropalladium Solvents: Toluene ;  10 min, 100 °C

Reference

Aminophosphine palladium pincer complexes for Suzuki and Heck reactions

Bolliger, Jeanne L.; Frech, Christian M., Chimia, 2009, 63(1-2), 23-28

Production Method 2

5122-95-2

37181-39-8

135654-48-7

92-06-8

Reaction Conditions

1.1 Reagents: Sodium bicarbonate Catalysts: Bis(tri-tert-butylphosphine)palladium Solvents: Dimethylformamide ;  6 h, 60 °C

Reference

Pd-catalyzed Suzuki-Miyaura cross-coupling of [Ph2SR][OTf] with arylboronic acids

Wang, Xiao-Yan; Song, Hai-Xia; Wang, Shi-Meng; Yang, Jing; Qin, Hua-Li; et al, Tetrahedron, 2016, 72(47), 7606-7612

Production Method 3

98-80-6

591-18-4

92-06-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium (nanoparticle complexes with a tris(polyethylene glycolyl triazolyl)benzene) ,  Poly(oxy-1,2-ethanediyl), α,α′,α′′-[1,3,5-benzenetriyltris(1H-1,2,3-triazole-4,1… (palladium complexes) Solvents: Acetone ,  Water ;  3 h, 60 °C; 60 °C → rt

Reference

Water-Soluble Palladium Nanoparticles: Click Synthesis and Applications as a Recyclable Catalyst in Suzuki Cross-Couplings in Aqueous Media

Mejias, Nereida; Pleixats, Roser; Shafir, Alexandr; Medio-Simon, Mercedes; Asensio, Gregorio, European Journal of Organic Chemistry, 2010, (26), 5090-5099

Production Method 4

98-80-6

591-18-4

92-06-8

Reaction Conditions

1.1 Reagents: Sodium carbonate Catalysts: Palladium diacetate Solvents: Dimethylformamide ,  Water ;  18 h, 60 °C

Reference

Preparation of polyphenyls

, China, , ,

Production Method 5

65844-89-5

92-06-8

Reaction Conditions

1.1 Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide
1.2 Solvents: Water
1.3 Solvents: Diethyl ether

Reference

Synthesis of mono-, di-, and triphenylarenes by sequential photostimulated SRN1 and Pd(0)-catalyzed cross coupling reactions on aryl halides

Corsico, Eduardo F.; Rossi, Roberto A., Synlett, 2000, (2), 230-232

Production Method 6

108-36-1

92-06-8

Reaction Conditions

1.1 Reagents: Potassium carbonate ,  Sodium iodide Catalysts: 2376473-55-9 Solvents: Dimethylformamide ;  6 h, 120 °C

Reference

Synthesis, Characterization and Theoretical Investigation on Thiazoline-Derived Palladium-Complexes-Catalyzed Denitrogenative Cross-Coupling of Aryl Halides with Arylhydrazines

Sudharsan, Murugesan; Thirumoorthy, Krishnan; Nethaji, Munirathinam; Suresh, Devarajan, ChemistrySelect, 2019, 4(32), 9253-9261

Production Method 7

92-06-8

Reaction Conditions

1.1 Catalysts: Grubbs second generation catalyst Solvents: Dichloromethane ;  2 h, rt
1.2 Catalysts: p-Toluenesulfonic acid ;  1 h, rt

Reference

Ring-closing olefin metathesis for the synthesis of benzene derivatives

Yoshida, Kazuhiro; Kawagoe, Fumihiro; Iwadate, Noriyuki; Takahashi, Hidetoshi; Imamoto, Tsuneo, Chemistry - An Asian Journal, 2006, 1(4), 611-613

Production Method 8

98-80-6

108-36-1

92-06-8

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: 2135789-70-5 Solvents: Dimethylformamide ;  12 h, 80 °C

Reference

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

Avinash, Iruthayaraj; Gupta, Vivek; Karthik, Vedhagiri; Anantharaman, Ganapathi, Journal of Organometallic Chemistry, 2017, 851, 104-114

Production Method 9

98-80-6

591-18-4

92-06-8

Reaction Conditions

1.1 Reagents: Sodium carbonate Catalysts: Palladium diacetate Solvents: Dimethylformamide ,  Water ;  12 h, 60 °C

Reference

Synthesis of Biaryls and Polyaryls by Ligand-Free Suzuki Reaction in Aqueous Phase

Liu, Leifang; Zhang, Yuhong; Xin, Bingwei, Journal of Organic Chemistry, 2006, 71(10), 3994-3997

Production Method 10

20104-40-9

92-06-8

Reaction Conditions

1.1 Reagents: Lithium Solvents: Tetrahydrofuran ;  24 h, rt

Reference

Electrostatic and Electrophilic Catalysis in the Reductive Cleavage of Alkyl Aryl Ethers. The Influence of Ion Pairing on the Regioselectivity

Casado, Francisco; Pisano, Luisa; Farriol, Maria; Gallardo, Iluminada; Marquet, Jordi; et al, Journal of Organic Chemistry, 2000, 65(2), 322-331

Production Method 11

98-80-6

92-06-8

Reaction Conditions

1.1 Reagents: Potassium hydroxide Catalysts: Palladium diacetate ,  2′-(Dicyclohexylphosphino)-N,N-dimethyl[1,1′-biphenyl]-2-amine Solvents: Toluene ;  7 - 8 h, 90 °C

Reference

Buchwald ligand-assisted Suzuki cross-coupling of polychlorobenzenes

Vasil'ev, Andrei A.; Burukin, Alexander S.; Zhdankina, Galina M.; Zlotin, Sergei G., Mendeleev Communications, 2021, 31(3), 400-402

Production Method 12

108-37-2

98-80-6

92-06-8

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: Palladium chloride ,  N2,N2,N6,N6-Tetrakis[(diphenylphosphino)methyl]-2,6-pyridinediamine Solvents: Dimethylacetamide ;  1 h, 100 °C
1.2 Solvents: o-Xylene ;  2 h, 90 °C

Reference

N,N,N',N'-tetra(diphenylphosphinomethyl)pyridine-2,6-diamine/palladium catalyzed Suzuki-Miyaura coupling of aryl and heteroaryl halides

Guo, Fei-chen; Zhou, Rong; Jiang, Zhi-jie; Wang, Wei; Fu, Hai-yan; et al, Catalysis Communications, 2015, 66, 87-90

Production Method 13

98-80-6

108-36-1

92-06-8

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: Benzene, diethenyl-, polymer with 1-(1,1-dimethylethyl)-4-ethenylbenzene ,  Pyridine, 4-ethenyl-, polymer with 1-(1,1-dimethylethyl)-4-ethenylbenzene Solvents: Ethanol ,  Tetrahydrofuran ,  Water ;  5 h, 70 °C
1.2 Solvents: Water

Reference

Continuous-Flow Suzuki-Miyaura Coupling in Water and Organic Solvents Promoted by Blends of Stabilized Convoluted Polymeric Palladium Catalysts and Polymeric Auxiliary Materials

Zhang, Zhenzhong; Ohno, Aya; Takaya, Hikaru; Yamada, Yoichi M. A., Chemistry - A European Journal, 2023, 29(34),

Production Method 14

20442-79-9

92-06-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium Solvents: Ethanol ;  60 min

Reference

The impact of the physical state and the reaction phase in the direct mechanocatalytic Suzuki-Miyaura coupling reaction

Yoo, Kwangho; Fabig, Sven; Graetz, Sven; Borchardt, Lars, Faraday Discussions, 2023, 241, 206-216

Production Method 15

98-80-6

108-36-1

92-06-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: 2230116-04-6 (post-treated with Pd(OAc)2) Solvents: Ethanol ;  0.5 h, 80 °C

Reference

Palladium Nanoparticle-Immobilized Porous Polyurethane Material for Quick and Efficient Heterogeneous Catalysis of Suzuki-Miyaura Cross-Coupling Reaction at Room Temperature

Dey, Sandeep Kumar; Dietrich, Dennis; Wegner, Susann; Gil-Hernandez, Beatriz; Harmalkar, Sarvesh Shyam; et al, ChemistrySelect, 2018, 3(5), 1365-1370

Production Method 16

5122-95-2

92-06-8

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: Palladium Solvents: Ethanol ,  Water ;  3 h, 60 °C

Reference

Phosphine-Built-in Porous Organic Cage for Stabilization and Boosting the Catalytic Performance of Palladium Nanoparticles in Cross-Coupling of Aryl Halides

Wang, Zhaozhan; Reddy, C. Bal; Zhou, Xin; Ibrahim, Jessica Juweriah; Yang, Yong, ACS Applied Materials & Interfaces, 2020, 12(47), 53141-53149

Production Method 17

92-06-8

Reaction Conditions

1.1 Catalysts: (SP-4-3)-[2,6-Bis[(diphenylphosphino-κP)amino]phenyl-κC]chloronickel Solvents: Tetrahydrofuran ;  18 h, 40 °C; 40 °C → rt
1.2 Solvents: Water ;  rt

Reference

Arylation of non-activated C-Cl bond with Grignard reagents catalyzed by pincer [PCP]-nickel complexes

Sun, Yunqiang; Li, Xiaoyan; Sun, Hongjian, Inorganica Chimica Acta, 2014, 415, 95-97

Production Method 18

98-80-6

108-36-1

92-06-8

Reaction Conditions

1.1 Reagents: Sodium carbonate Catalysts: Tetraamminedichloropalladium(2+) Solvents: Dimethylacetamide ,  Water ;  15 min, 100 °C

Reference

Pd-loaded NaY zeolite as a highly active catalyst for ligandless Suzuki-Miyaura reactions of aryl halides at low Pd loadings under aerobic conditions

Durgun, Gulay; Aksin, Ozge; Artok, Levent, Journal of Molecular Catalysis A: Chemical, 2007, 278(1-2), 189-199

Production Method 19

92-06-8

Reaction Conditions

1.1 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Ethyl acetate ;  rt

Reference

Assembly of unsymmetrical 1,3,5-triarylbenzenes via tandem reaction of β-arylethenesulfonyl fluorides and α-cyano-β-methylenones

Zhang, Fang; An, Yi; Liu, Jichang; Du, Guangfen; Cai, Zhihua; et al, New Journal of Chemistry, 2022, 46(25), 12367-12371

M-Terphenyl Raw materials

• 1-Bromo-3-chlorobenzene
• Phenylboronic acid
• Stannane, 1,3-phenylenebis[trimethyl-
• 1,1'-Biphenyl, 3-iodo-
• 1-Bromo-3-iodobenzene
• 3-Biphenylboronic acid
• 1,3-Dibromobenzene
• 1,1':3',1''-Terphenyl, 2'-methoxy-
• Diphenyl(2,2,2-trifluoroethyl)sulfonium

M-Terphenyl Preparation Products

• M-Terphenyl (92-06-8)

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  Fereshteh Bayat Environ. Sci.: Nano, 2021,8, 367-389
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  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 5. Evolution of cellulose into flexible conductive green electronics: a smart strategy to fabricate sustainable electrodes for supercapacitors
  Tengfei Yu,Yuehan Wu,Wei Li,Bin Li RSC Adv., 2014,4, 34134-34143

• Solvents and Organic Chemicals Organic Compounds Hydrocarbons

M-Terphenyl (CAS No. 92-06-8): A Comprehensive Overview

M-Terphenyl, also known as 1,3,5-trimethylbenzene, is a chemical compound with the CAS registry number 92-06-8. This compound is a derivative of benzene, featuring three methyl groups attached to the aromatic ring at the meta positions. M-Terphenyl has been extensively studied for its unique chemical properties and wide-ranging applications in various fields such as organic electronics, materials science, and biomedicine.

Chemical Structure and Properties

M-Terphenyl's molecular formula is C₁₄H₁₄, with a molecular weight of 178.25 g/mol. The compound exhibits a melting point of approximately 13°C and a boiling point around 255°C under standard conditions. Its solubility in water is low, making it more soluble in organic solvents such as dichloromethane and toluene.

Synthesis Methods

M-Terphenyl can be synthesized through various methods, including Friedel-Crafts alkylation, Ullmann coupling, and Suzuki-Miyaura coupling reactions. Recent advancements in catalytic processes have enabled more efficient and environmentally friendly synthesis routes for M-Terphenyl.

Applications in Organic Electronics

M-Terphenyl has gained significant attention in the field of organic electronics due to its high electron mobility and stability under thermal and electrical stress. It is commonly used as a charge transport layer in organic light-emitting diodes (OLEDs) and organic photovoltaic (OPV) devices.

Recent Research Developments

Recent studies have explored the use of M-Terphenyl as a building block for advanced materials such as perovskite solar cells and flexible electronics. Researchers have also investigated its potential as a drug delivery agent in nanotechnology applications.

Environmental Impact and Safety Considerations

M-Terphenyl is generally considered non-toxic under normal handling conditions. However, prolonged exposure to high concentrations may cause irritation to the eyes and skin. Proper safety precautions should be taken during handling and storage.

In conclusion, M-Terphenyl (CAS No. 92-06-8) remains a versatile compound with promising applications across multiple disciplines. Ongoing research continues to unlock new possibilities for this compound, making it an essential component in modern material science and technology.

• 1166-19-4(m,p-Quaterphenyl)
• 14739-51-6(1,1':4',1'':3'',1''':4''',1'''':4'''',1'''''-Sexiphenyl(7CI,8CI,9CI))
• 102814-13-1(Carbonic acid, diphenyl ester, polymer with 1,4-butanediol, 1,6-hexanediol,alpha-hydro-omega-hydroxypoly(oxy(methyl-1,2-ethanediyl)) and 1,1-methylenebis(4-isocyanatobenzene))
• 1486-01-7(1,1’-Diphenyl-D10)
• 16716-11-3(1,1':3',1'':3'',1''':3''',1'''':3'''',1''''':3''''',1'''''':3'''''',1'''''''-Octiphenyl)
• 29036-02-0(m-Quaterphenyl)
• 26140-60-3(Terphenyl)
• 98904-43-9(P-TERPHENYL-D14)
• 94363-13-0(1,4-diphenylbenzene)
• 1718-51-0(p-Terphenyl-d14)