Production Method 1

1131-61-9

939-23-1

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Tetrabutylammonium bromide ,  Rhenium, [2-(mercapto-κS)benzenemethanethiolato(2-)-κS]methyloxo(triphenylphosph… Solvents: Benzene ,  Water

Reference

Rhenium, [2-(mercapto-κS)benzenemethanethiolato(2-)-κS]methyloxo(triphenylphosphine)

Meyers, David J., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2013, 1,

Production Method 2

1131-61-9

939-23-1

Reaction Conditions

1.1 Reagents: Triphenylphosphine Catalysts: Rhenium, [2-(mercapto-κS)benzenemethanethiolato(2-)-κS]methyloxo(triphenylphosph… Solvents: Benzene

Reference

Efficient catalytic conversion of pyridine N-oxides to pyridine with an oxorhenium(V) catalyst

Wang, Ying; Espenson, James H., Organic Letters, 2000, 2(22), 3525-3526

Production Method 3

1131-61-9

939-23-1

Reaction Conditions

1.1 Reagents: Dimethylphenylsilane Catalysts: Hydroxylapatite (Ca5(OH)(PO4)3) ,  Gold Solvents: 1,4-Dioxane ;  1 h, 1 atm, 30 °C

Reference

Preparation of pyridine compounds by deoxygenation of pyridine N-oxides using supported gold nanoparticle catalysts and silanes

, Japan, , ,

Production Method 4

1131-61-9

939-23-1

Reaction Conditions

1.1 Reagents: Triphenylphosphine Catalysts: Rhenium, trioxo(3,8,13,16-tetraphenyl-4,7-imino-2,17-metheno-9,12-nitrilo[1,3]di… Solvents: Dichloromethane ;  1 h, 23 °C

Reference

Catalytic deoxygenation of pyridine N-oxides with N-fused porphyrin rhenium complexes

Toganoh, Motoki; Fujino, Keitaro; Ikeda, Shinya; Furuta, Hiroyuki, Tetrahedron Letters, 2008, 49(9), 1488-1491

Production Method 5

1131-61-9

939-23-1

Reaction Conditions

1.1 Reagents: Triphenylphosphine Catalysts: Rhenium, trioxo(3,8,13,16-tetraphenyl-4,7-imino-2,17-metheno-9,12-nitrilo[1,3]di… Solvents: Toluene ;  1 h, 26 °C

Reference

Re(VII) complex of N-fused tetraphenylporphyrin

Toganoh, Motoki; Ikeda, Shinya; Furuta, Hiroyuki, Chemical Communications (Cambridge, 2005, (36), 4589-4591

Production Method 6

1131-61-9

939-23-1

Reaction Conditions

1.1 Reagents: Bis(neopentyl glycolato)diboron Solvents: Benzene-d6 ;  3 h, 70 °C

Reference

Diboron reagents in the deoxygenation of nitrones

Vargas, Emily L.; Franco, Mario; Alonso, Ines; Tortosa, Mariola; Belen Cid, M., Organic & Biomolecular Chemistry, 2023, 21(4), 807-816

Production Method 7

98-80-6

626-61-9

939-23-1

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: Palladium (WA30 anion exchange resin) Solvents: Dimethylacetamide ;  12 h, 80 °C

Reference

Development of a Unique Heterogeneous Palladium Catalyst for the Suzuki-Miyaura Reaction using (Hetero)aryl Chlorides and Chemoselective Hydrogenation

Ichikawa, Tomohiro; Netsu, Moeko; Mizuno, Masahiro; Mizusaki, Tomoteru; Takagi, Yukio; et al, Advanced Synthesis & Catalysis, 2017, 359(13), 2269-2279

Production Method 8

98-80-6

626-61-9

939-23-1

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Dichloro(dicyclohexylphenylphosphine)[tris(1,1-dimethylethyl)phosphine]palladium (polypropylene-bound) Solvents: Ethanol ,  Water ;  15 h, 75 °C

Reference

Tunable Palladium-FibreCats for Aryl Chloride Suzuki Coupling with Minimal Metal Leaching

Colacot, Thomas J.; Carole, William A.; Neide, Bruce A.; Harad, Ajay, Organometallics, 2008, 27(21), 5605-5611

Production Method 9

1131-61-9

939-23-1

Reaction Conditions

1.1 Reagents: 1-Chloromethanesulfonyl chloride ;  24 h, 90 °C

Reference

One-step conversion of pyridine N-oxides to tetrazolo[1,5-a]pyridines

Keith, John M., Journal of Organic Chemistry, 2006, 71(25), 9540-9543

Production Method 10

98-80-6

1120-87-2

939-23-1

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

Efficient coupling of heteroaryl halides with arylboronic acids in the presence of a palladium-tetraphosphine catalyst

Feuerstein, Marie; Doucet, Henri; Santelli, Maurice, Journal of Organometallic Chemistry, 2003, 687(2), 327-336

Production Method 11

98-80-6

626-61-9

939-23-1

Reaction Conditions

1.1 Reagents: Potassium carbonate ,  Tetrabutylammonium bromide Catalysts: Di-μ-chlorobis[5-hydroxy-2-[1-(hydroxyimino-κN)ethyl]phenyl-κC]dipalladium Solvents: Water ;  3.5 h, reflux
1.2 Solvents: Ethyl acetate

Reference

Cross-coupling reactions with boronic acids in water catalysed by oxime-derived palladacycles

Botella, Luis; Najera, Carmen, Journal of Organometallic Chemistry, 2002, 663(1-2), 46-57

Production Method 12

98-80-6

19524-06-2

939-23-1

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

Reference

Efficient coupling of heteroaryl bromides with arylboronic acids in the presence of a palladium-tetraphosphine catalyst

Feuerstein, M.; Doucet, H.; Santelli, M., Tetrahedron Letters, 2001, 42(33), 5659-5662

Production Method 13

98-80-6

15854-87-2

939-23-1

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Magnesium oxide ,  2759016-37-8 Solvents: 1,2-Dimethoxyethane ;  24 h, 100 °C

Reference

Molecular engineered palladium single atom catalysts with an M-C1N3 subunit for Suzuki coupling

Liu, Jia; Chen, Zhongxin; Liu, Cuibo; Zhang, Bao; Du, Yonghua; et al, Journal of Materials Chemistry A: Materials for Energy and Sustainability, 2021, 9(18), 11427-11432

Production Method 14

1131-61-9

939-23-1

Reaction Conditions

1.1 Reagents: Triphenylphosphine Catalysts: (SP-5-15)-[4-Methyl-2,7,12,17-tetraphenyl-4,21,22,23-tetraazapentacyclo[16.2.1.1… Solvents: Toluene ;  24 h, 80 °C

Reference

Cooperation between metal and ligand in oxygen atom transport by N-confused porphyrin oxorhenium(V) complexes

Yamamoto, Takaaki; Toganoh, Motoki; Furuta, Hiroyuki, Dalton Transactions, 2012, 41(30), 9154-9157

Production Method 15

1131-61-9

939-23-1

Reaction Conditions

1.1 Reagents: Dimethylphenylsilane Catalysts: Gold (hydroxyapatite-supported nanoparticle) Solvents: 1,4-Dioxane ;  1 h, 30 °C

Reference

Highly efficient gold nanoparticle catalyzed deoxygenation of amides, sulfoxides, and pyridine N-oxides

Mikami, Yusuke; Noujima, Akifumi; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; et al, Chemistry - A European Journal, 2011, 17(6), 1768-1772

Production Method 16

98-80-6

1120-87-2

939-23-1

Reaction Conditions

1.1 Reagents: Sodium carbonate Catalysts: Palladium (metal-organic gel supported) Solvents: Methanol ;  rt → 60 °C; 1 h, 60 °C

Reference

Metal-organic gels as functionalisable supports for catalysis

Zhang, Jianyong; Wang, Xiaobing; He, Lisi; Chen, Liuping; Su, Cheng-Yong; et al, New Journal of Chemistry, 2009, 33(5), 1070-1075

4-Phenylpyridine Raw materials

• Phenylboronic acid
• 4-Chloropyridine
• 4-bromopyridine
• 4-Phenylpyridine N-oxide
• 4-Bromopyridine hydrochloride
• 4-Iodopyridine

4-Phenylpyridine Preparation Products

• 4-Phenylpyridine (939-23-1)

• 1. An artificial photosynthetic system for photoaccumulation of two electrons on a fused dipyridophenazine (dppz)–pyridoquinolinone ligand?
  Philipp Traber,Stephan Kupfer,Stefanie Gr?fe,Isabelle Baussanne,Martine Demeunynck,Jean-Marie Mouesca,Serge Gambarelli,Vincent Artero,Murielle Chavarot-Kerlidou Chem. Sci., 2018,9, 4152-4159
• 2. An intermolecular C–H oxidizing strategy to access highly fused carbazole skeletons from simple naphthylamines?
  Christian K. Rank,Alexander W. Jones,Tatjana Wall,Patrick Di Martino-Fumo,Sarah Schr?ck,Markus Gerhards,Frederic W. Patureau Chem. Commun., 2019,55, 13749-13752
• 3. An approach to 7-aza-1-phosphanorbornane complexes: strain promoted rearrangement of 1-iminylphosphirane complexes and cycloaddition with olefins?
  Yang Xu,Min Wang,Donghui Wei,Rongqiang Tian,Zheng Duan,Fran?ois Mathey Dalton Trans., 2019,48, 5523-5526
• 4. An Assessment of the Laminar Hypersonic Double-Cone Experiments in the LENS-XX Tunnel
  JaideepRay,PatrickBlonigan,EricT.Phipps,KathrynMaupin
• 5. Alternative mixtures to R-600a. Theoretical assessment and experimental energy evaluation of binary mixtures in a commercial cooler: Mélanges alternatifs au R-600a. évaluation théorique et évaluation énergétique expérimentale de mélanges binaires dans un refroidisseur commercial.
  DanielCalleja-Anta,DanielSánchez,LauraNebot-Andres,RamónCabello,RodrigoLlopis

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

• 553-26-4(4-(pyridin-4-yl)pyridine)
• 921205-05-2(Pyridine, 4,4'-[5'-[3-(4-pyridinyl)phenyl][1,1':3',1''-terphenyl]-3,3''-diyl]bis-)
• 123333-55-1(4,4'-Dipyridine hydrate)
• 37275-48-2(Bipyridine)
• 4423-10-3(4-(p-Tolyl)pyridine)
• 27926-72-3(4,4'-Bipyridine Dihydrochloride)
• 132125-39-4(4,4'-dipyridyl-d8)
• 111876-50-7(Pyridine, 4-(2-naphthalenyl)-)
• 113682-56-7(bpbenz)
• 861024-61-5(Pyridine,4-[1,1'-biphenyl]-4-yl-)