Production Method 1

109674-45-5

625-92-3

92-07-9

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: (SP-4-4)-Chloro[2-[1-[(4-methylphenyl)imino-κN]ethyl]ferrocenyl-κC](triphenylpho… Solvents: Ethanol ,  Water ;  4 h, 90 °C

Reference

Palladacycle-catalyzed Suzuki-Miyaura reaction of aryl/heteroaryl halides with MIDA boronates in EtOH/H2O or H2O

Li, Yabo; Wang, Jingran; Wang, Zhiwei; Huang, Mengmeng; Yan, Beiqi; et al, RSC Advances, 2014, 4(68), 36262-36266

Production Method 2

2457-47-8

98-80-6

92-07-9

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water ;  rt → 100 °C
1.2 Reagents: Polyaniline Catalysts: Palladium ;  6 h, 100 °C

Reference

Palladium nanoparticles supported on polyaniline nanofibers as a semi-heterogeneous catalyst in water

Gallon, Benjamin J.; Kojima, Robert W.; Kaner, Richard B.; Diaconescu, Paula L., Angewandte Chemie, 2007, 46(38), 7251-7254

Production Method 3

92-07-9

Reaction Conditions

1.1 Catalysts: Scandium triflate Solvents: 1,4-Dioxane ;  15 min, rt
1.2 Reagents: Ammonia Catalysts: Iron chloride (FeCl3) Solvents: Tetrahydrofuran ;  rt; 30 min, rt; rt → 110 °C; 24 h, 110 °C

Reference

Sc(OTf)3-Mediated One-Pot Synthesis of 3,4-Disubstituted 1H-Pyrazoles and 3,5-Disubstituted Pyridines from Hydrazine or Ammonia with Epoxides

Mehedi, Shafaat Al Md; George, Dare E. ; Tepe, Jetze J., Journal of Organic Chemistry, 2022, 87(24), 16820-16828

Production Method 4

53710-18-2

4406-72-8

92-07-9

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: Cupric chloride Solvents: Dimethylformamide ;  24 h, 110 °C
1.2 Solvents: Water ;  110 °C

Reference

Insight into Copper Catalysis: In Situ Formed Nano Cu2O in Suzuki-Miyaura Cross-Coupling of Aryl/Indolyl Boronates

Ranjani, Ganapathy; Nagarajan, Rajagopal, Organic Letters, 2017, 19(15), 3974-3977

Production Method 5

92-07-9

Reaction Conditions

Reference

Alkaline cleavage of (1-phenylsulfonyl-2-pyrazolin-5-yl)methyl ketones and related compounds

Lempert-Sreter, M.; Lempert, K., Tetrahedron, 1975, 31(15), 1677-82

Production Method 6

122-78-1

92-07-9

Reaction Conditions

1.1 Reagents: Ammonium iodide Solvents: Dimethylformamide ;  6 h, 130 °C

Reference

Selective Synthesis of Substituted Pyridines and Pyrimidines through Cascade Annulation of Isopropene Derivatives

Li, Jian; Li, Jiaming; He, Runfa; Liu, Jiasheng; Liu, Yang; et al, Organic Letters, 2022, 24(8), 1620-1625

Production Method 7

150-30-1

92-07-9

Reaction Conditions

1.1 Reagents: Acetic acid Catalysts: Iodine Solvents: Dimethyl sulfoxide ;  6 h, 115 °C

Reference

Molecular Iodine-Mediated Chemoselective Synthesis of Multisubstituted Pyridines through Catabolism and Reconstruction Behavior of Natural Amino Acids

Xiang, Jia-Chen; Wang, Miao; Cheng, Yan; Wu, An-Xin, Organic Letters, 2016, 18(1), 24-27

Production Method 8

122-78-1

92-07-9

Reaction Conditions

1.1 Reagents: Water ,  Ceric ammonium nitrate Catalysts: Acetic acid, 2,2,2-trifluoro-, copper(2+) salt (2:1) Solvents: Dimethylformamide ;  12 h, 80 °C

Reference

Cu-Catalyzed Concise Synthesis of Pyridines and 2-(1H)-Pyridones from Acetaldehydes and Simple Nitrogen Donors

Li, Ziyuan; Huang, Xiaoqiang; Chen, Feng; Zhang, Chun; Wang, Xiaoyang; et al, Organic Letters, 2015, 17(3), 584-587

Production Method 9

92-07-9

Reaction Conditions

1.1 Reagents: Formic acid ,  Triethylamine Catalysts: Palladium diacetate ,  1,3-Bis(diphenylphosphino)propane Solvents: Dimethylformamide ;  1 h, 60 °C; cooled
1.2 Reagents: Water ;  cooled

Reference

Synthesis of Trisubstituted Pyridines via Chemoselective Suzuki-Miyaura Coupling of 3,5- and 4,6-Dibromo-2-tosyloxypyridines

Park, Cho-Hee; Kwon, Yong-Ju; Oh, In-Young; Kim, Won-Suk, Advanced Synthesis & Catalysis, 2017, 359(1), 107-119

Production Method 10

5153-67-3

92-07-9

Reaction Conditions

1.1 Reagents: Iron Solvents: Acetic acid ;  30 min, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  neutralized

Reference

Iron-Mediated One-Pot Synthesis of 3,5-Diarylpyridines from β-Nitrostyrenes

Sathish, Manda; Chetna, Jadala; Hari Krishna, Namballa; Shankaraiah, Nagula; Alarifi, Abdullah; et al, Journal of Organic Chemistry, 2016, 81(5), 2159-2165

Production Method 11

98-80-6

625-92-3

92-07-9

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: 1-Hexanamine, N,N′-methanetetraylbis-, homopolymer (composite with palladium) Solvents: 1,4-Dioxane ;  19 h, reflux

Reference

Synthesis and catalytic activity of a poly(N,N-dialkylcarbodiimide)/palladium nanoparticle composite: a case in the Suzuki coupling reaction using microwave and conventional heating

Liu, Yubiao; Khemtong, Chalermchai; Hu, Jun, Chemical Communications (Cambridge, 2004, (4), 398-399

Production Method 12

98-80-6

625-92-3

92-07-9

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Di-μ-chlorobis(η3-2-propenyl)dipalladium ,  rel-1,1′,1′′,1′′′-[(1R,2R,3S,4S)-1,2,3,4-Cyclopentanetetrayltetrakis(methylene)]… Solvents: Xylene ;  20 h, 130 °C

Reference

Reaction of aryl di-, tri-, or tetrabromides with arylboronic acids or alkenes in the presence of a palladium-tetraphosphine catalyst

Berthiol, Florian; Kondolff, Isabelle; Doucet, Henri; Santelli, Maurice, Journal of Organometallic Chemistry, 2004, 689(17), 2786-2798

Production Method 13

98-80-6

625-92-3

92-07-9

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium Solvents: Ethanol ;  2 h, 65 °C

Reference

Fabrication and Application of Graphene Supported Diimine-Palladium Complex Catalyst for Organic Synthesis

Sun, Yunlong; Li, Tian, ChemistrySelect, 2020, 5(4), 1431-1438

Production Method 14

150-30-1

92-07-9

Reaction Conditions

1.1 Reagents: Cupric acetate ,  Iron chloride (FeCl3) Catalysts: Palladium diacetate ,  2′-(Dicyclohexylphosphino)-N,N-dimethyl[1,1′-biphenyl]-2-amine Solvents: Dimethyl sulfoxide ,  Dimethylformamide ;  16 h, 120 °C

Reference

Pd-Catalyzed Decarboxylation and Dual C(sp3)-H Functionalization Protocols for the Synthesis of 2,4-Diarylpyridines

Gujjarappa, Raghuram ; Vodnala, Nagaraju; Kumar, Mohan; Malakar, Chandi C., Journal of Organic Chemistry, 2019, 84(9), 5005-5020

Production Method 15

24388-23-6

625-92-3

92-07-9

Reaction Conditions

1.1 Reagents: Sodium carbonate Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ,  Water ;  rt; 12 h, 80 °C

Reference

Olefin Cyclopropanation by Radical Carbene Transfer Reactions Promoted by Cobalt(II)/Porphyrinates: Active-Metal-Template Synthesis of [2]Rotaxanes

Alcantara, Arthur F. P.; Fontana, Liniquer A.; Rigolin, Vitor H.; Andrade, Yuri F. S.; Ribeiro, Marcos A. ; et al, Angewandte Chemie, 2018, 57(29), 8979-8983

Production Method 16

98-80-6

625-92-3

92-07-9

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium Solvents: Methanol ,  Acetonitrile ;  3.5 h, rt

Reference

Palladium nanoparticles catalyzed Suzuki cross-coupling reactions in ambient conditions

Mandali, Pavan Kumar; Chand, Dillip Kumar, Catalysis Communications, 2013, 31, 16-20

Production Method 17

98-80-6

625-92-3

92-07-9

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: Triphenylphosphine Solvents: Dimethylacetamide ;  12 h, 130 °C

Reference

Transition-Metal-Free Coupling Reactions: PPh3-Promoted Sonogashira-Type Cross-Couplings of Heteroaryl Halides with Terminal Alkynes

Tian, Wan-Fa; He, Ke-Han; Li, Na; Fen; Liu; et al, ChemistrySelect, 2020, 5(15), 4496-4499

Production Method 18

122-78-1

92-07-9

Reaction Conditions

1.1 Reagents: Sodium bicarbonate ,  Ammonium acetate ,  Oxygen Solvents: 1,4-Dioxane ;  5 h, 90 °C

Reference

Metal-free synthesis of substituted pyridines from aldehydes and NH4OAC under air

Yan, Rulong; Zhou, Xiaoqiang; Li, Ming; Li, Xiaoni; Kang, Xing; et al, RSC Advances, 2014, 4(92), 50369-50372

Production Method 19

98-80-6

625-92-3

92-07-9

Reaction Conditions

1.1 Reagents: Potassium hydroxide Catalysts: Palladium, bis(6-methyl-α,α-diphenyl-2-pyridineethanolato-κN1,κO2)-, compd. with… Solvents: Ethanol ;  7 h, 50 °C

Reference

The catalytic activity of a novel recyclable alkoxypalladium complex in Suzuki reaction

Li, Yabo; Mi, Xia; Huang, Mengmeng; Cai, Ranran; Wu, Yangjie, Tetrahedron, 2012, 68(40), 8502-8508

Production Method 20

619-55-6

92-07-9

5209-18-7

99-94-5

Reaction Conditions

1.1 Reagents: Sulfolane ,  Cesium carbonate ;  24 h, 135 °C

Reference

Base-Promoted One-Pot Synthesis of Pyridine Derivatives via Aromatic Alkyne Annulation Using Benzamides as Nitrogen Source

Mehmood, Hina; Iqbal, Muhammad Asif; Ashiq, Muhammad Naeem; Hua, Ruimao, Molecules, 2021, 26(21),

3,5-Diphenylpyridine Raw materials

• 3,5-Dichloropyridine
• Phenylboronic acid
• trans-b-Nitrostyrene
• 3,5-Diiodopyridine
• 1,3,2-Dioxaborolane, 2-phenyl-
• 2-phenylacetaldehyde
• 2-Phenyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
• 4-Methylbenzamide
• Phenylboronic Acid Pinacol Ester
• 3,5-Dibromopyridine
• DL-3-Phenylalanine

3,5-Diphenylpyridine Preparation Products

• 1,3-diphenylpropene (5209-18-7)
• 4-Methylbenzoic acid (99-94-5)
• 3,5-Diphenylpyridine (92-07-9)

• 1. An astrophysically-relevant mechanism for amino acid enantiomer enrichment
  Stephen P. Fletcher,Richard B. C. Jagt,Ben L. Feringa Chem. Commun., 2007, 2578-2580
• 2. Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers
  P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. Buda Phys. Chem. Chem. Phys., 2011,13, 10270-10279
• 3. An atomically efficient, highly stable and redox active Ce0.5Tb0.5Ox (3% mol.)/MgO catalyst for total oxidation of methane?
  Juan J. Sánchez,Miguel López-Haro,Juan C. Hernández-Garrido,Ginesa Blanco,Miguel A. Cauqui,José M. Rodríguez-Izquierdo,José A. Pérez-Omil,José J. Calvino,María P. Yeste J. Mater. Chem. A, 2019,7, 8993-9003
• 4. An assessment of strategies for the development of solid-state adsorbents for vehicular hydrogen storage
  Mark D. Allendorf,Alauddin Ahmed,Tom Autrey,Jeffrey Camp,Eun Seon Cho,Maciej Haranczyk,Abhi Karkamkar,Di-Jia Liu,Katie R. Meihaus,Iffat H. Nayyar,Roman Nazarov,Donald J. Siegel,Vitalie Stavila,Jeffrey J. Urban,Srimukh Prasad Veccham,Brandon C. Wood Energy Environ. Sci., 2018,11, 2784-2812
• 5. An algal process treatment combined with the Fenton reaction for high concentrations of amoxicillin and cefradine
  Haitao Li,Yu Pan,Zhizhi Wang,Shan Chen,Ruixin Guo,Jianqiu Chen RSC Adv., 2015,5, 100775-100782

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Phenylpyridines

Professional Introduction to 3,5-Diphenylpyridine (CAS No. 92-07-9)

3,5-Diphenylpyridine, with the chemical formula C₁₄H₁₀N, is a heterocyclic organic compound belonging to the pyridine class. Its CAS number, CAS No. 92-07-9, uniquely identifies it in the chemical industry and research communities. This compound has garnered significant attention due to its versatile applications in pharmaceuticals, agrochemicals, and material science. The presence of two phenyl rings attached to the pyridine core imparts unique electronic and steric properties, making it a valuable scaffold for further chemical modifications and functionalizations.

The synthesis of 3,5-Diphenylpyridine typically involves condensation reactions between appropriate precursors, such as benzaldehyde derivatives and amidines. Advanced synthetic methodologies have been developed to enhance yield and purity, ensuring that the final product meets stringent industry standards. Recent advancements in catalytic processes have enabled more efficient and environmentally friendly routes to this compound, aligning with global sustainability initiatives.

In the realm of pharmaceutical research, 3,5-Diphenylpyridine has emerged as a promising intermediate in the development of novel therapeutic agents. Its structural motif is found in several bioactive molecules that exhibit inhibitory effects on various biological targets. For instance, derivatives of this compound have shown potential in inhibiting kinases and other enzymes involved in cancer pathways. Preliminary studies indicate that modifications to the phenyl rings can fine-tune the pharmacokinetic properties of these derivatives, leading to improved drug efficacy and reduced side effects.

Moreover, the agrochemical industry has explored the use of 3,5-Diphenylpyridine based compounds for their herbicidal and pesticidal properties. The unique interaction between the pyridine ring and biological systems allows for selective targeting of pests while minimizing environmental impact. Researchers are currently investigating novel formulations that leverage this compound's properties to develop next-generation agrochemicals that are both effective and sustainable.

The material science applications of 3,5-Diphenylpyridine are equally fascinating. Its conjugated system makes it a candidate for use in organic electronics, such as light-emitting diodes (OLEDs) and photovoltaic cells. The ability to modify its structure allows for tuning its electronic characteristics, making it adaptable for various optoelectronic devices. Additionally, its stability under different environmental conditions enhances its suitability for industrial applications where durability is crucial.

Recent research has also highlighted the role of 3,5-Diphenylpyridine in medicinal chemistry as a key intermediate in the synthesis of antiviral agents. The compound's ability to interact with viral proteases and polymerases has been exploited to develop inhibitors that can disrupt viral replication cycles. These findings are particularly relevant in the context of emerging infectious diseases where rapid development of antiviral therapies is essential.

The industrial production of CAS No. 92-07-9, or 3,5-Diphenylpyridine, adheres to rigorous quality control measures to ensure consistency and reliability. Manufacturers employ state-of-the-art analytical techniques such as high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy to verify purity and structural integrity. These measures are critical in pharmaceutical applications where even minor impurities can affect drug safety and efficacy.

In conclusion, 3,5-Diphenylpyridine represents a multifaceted compound with broad utility across multiple industries. Its unique structural features make it a valuable building block for pharmaceuticals, agrochemicals, and advanced materials. Ongoing research continues to uncover new applications and refine synthetic methodologies, ensuring that this compound remains at the forefront of chemical innovation.

• 79412-31-0(Pyridine, 3-(3-methylphenyl)-, hydrochloride)
• 1008-88-4(3-Phenylpyridine)
• 4423-09-0(Pyridine,3-(4-methylphenyl)-)
• 106047-36-3(3,3':5',3''-Terpyridine)
• 106047-39-6(3,3':5',4''-Terpyridine)
• 921205-02-9(TpPyPB)
• 10477-94-8(3-Methyl-5-phenylpyridine)
• 106047-37-4(4,3':5',4''-Terpyridine)
• 1030380-38-1(1,3-Bis[3,5-di(pyridin-3-yl)phenyl]benzene)
• 921205-03-0(TmPyPB)