Production Method 1

98-80-6

3437-95-4

825-55-8

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; et al, Journal of Organometallic Chemistry, 2003, 687(2), 327-336

Production Method 2

98-80-6

3437-95-4

825-55-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium Solvents: Ethanol ,  Water ;  24 h, 80 °C

Reference

PdNP@Cyclodextrin on Cu/Al LDH-containing nanocomposites: Cage effect, crystallite size tuning and composite topology towards cross-couplings

Neves, Vinicius A.; et al, Applied Clay Science, 2022, 230,

Production Method 3

591-50-4

54663-78-4

825-55-8

Reaction Conditions

1.1 Reagents: Lithium chloride Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ;  480 min, 85 °C

Reference

Dual Effect of Halides in the Stille Reaction: In Situ Halide Metathesis and Catalyst Stabilization

Verbeeck, Stefan; et al, Chemistry - A European Journal, 2010, 16(43), 12831-12837

Production Method 4

1003-09-4

825-55-8

Reaction Conditions

1.1 Catalysts: Triphenylphosphine ,  Palladium, [N,N′-bis[3-(triethoxysilyl)propyl][2,2′-bipyridine]-4,4′-dimethanami… (MCM-41-anchored) Solvents: Tetrahydrofuran ;  15 h, reflux

Reference

Anchored palladium bipyridyl complex in nanosized MCM-41: A recyclable and efficient catalyst for the Kumada-Corriu reaction

Tsai, Fu-Yu; et al, Tetrahedron, 2007, 63(20), 4304-4309

Production Method 5

1003-09-4

825-55-8

Reaction Conditions

1.1 Catalysts: 2093415-82-6 Solvents: Tetrahydrofuran ;  16 h, 50 °C
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Three Different Reactions, One Catalyst: A Cu(I) PNP Pincer Complex as Catalyst for C-C and C-N Cross-Couplings

Mastalir, Matthias ; et al, Organic Letters, 2017, 19(8), 2178-2181

Production Method 6

6165-68-0

825-55-8

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Tetrahydrofuran ,  Water ;  5 min, 24 °C
1.2 Catalysts: Palladium diacetate ,  Tri-tert-butylphosphine Solvents: Tetrahydrofuran ;  5 min, 24 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Flash Generation of a Highly Reactive Pd Catalyst for Suzuki-Miyaura Coupling by Using a Flow Microreactor

Nagaki, Aiichiro; et al, Chemistry - A European Journal, 2012, 18(38), 11871-11875

Production Method 7

6165-68-0

825-55-8

Reaction Conditions

1.1 Reagents: Cesium carbonate ,  Tetrabutylammonium bromide Catalysts: Cuprous iodide Solvents: Dimethyl sulfoxide ;  21 h, 135 - 140 °C

Reference

TBAB-promoted ligand-free copper-catalyzed cross-coupling reactions of aryl halides with arylboronic acids

Li, Jin-Heng; et al, Synthesis, 2007, (7), 984-988

Production Method 8

3437-95-4

825-55-8

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: 9,9′-(1,2-Ethanediyldiimino)bis[1H-phenalen-1-one] ;  12 h, 130 °C
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Accessing Heterobiaryls through Transition-Metal-Free C-H Functionalization

Banik, Ananya; et al, Journal of Organic Chemistry, 2018, 83(6), 3236-3244

Production Method 9

3437-95-4

825-55-8

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: 2,2′-(1E)-1,2-Diazenediylbis[2,4-dimethylpentanenitrile] Solvents: Benzene ;  3 h, 110 °C

Reference

AMVN-initiated expedient synthesis of biaryls by the coupling reaction of unactivated arenes and heteroarenes with aryl iodides

Bhakuni, Bhagat Singh; et al, New Journal of Chemistry, 2014, 38(2), 827-836

Production Method 10

3437-95-4

825-55-8

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: Graphene (oxide; phenalenyl-grafted) ;  12 h, 130 °C

Reference

Graphene oxide-phenalenyl composite: transition metal-free recyclable and catalytic C-H functionalization

Singh, Bhagat; et al, Chemical Communications (Cambridge, 2018, 54(94), 13220-13223

Production Method 11

591-50-4

6165-68-0

825-55-8

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: Ruthenium (sulfur modified, Au supported) Solvents: 1,2-Dimethoxyethane ;  6 h, 80 °C; 80 °C → rt
1.2 Solvents: Water ;  10 h, 100 °C

Reference

Ligand-free Suzuki-Miyaura coupling using ruthenium(0) nanoparticles and a continuously irradiating microwave system

Akiyama, Toshiki; et al, Green Chemistry, 2017, 19(14), 3357-3369

Production Method 12

98-80-6

10486-61-0

825-55-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium Solvents: Ethanol ,  Water ;  5 h, 90 °C

Reference

Palladium Nanoparticles Immobilized on an Aminopropyl-functionalized Silica-Magnetite Composite as a Recyclable Catalyst for Suzuki-Miyaura Reactions

Lati, Monireh Pourghasemi; et al, ChemistrySelect, 2018, 3(27), 7970-7975

Production Method 13

98-80-6

10486-61-0

825-55-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium ,  Agarose Solvents: Water ;  1 h, 80 °C

Reference

Agarose hydrogel as an effective bioorganic ligand and support for the stabilization of palladium nanoparticles. Application as a recyclable catalyst for Suzuki-Miyaura reaction in aqueous media

Firouzabadi, Habib; et al, RSC Advances, 2011, 1(6), 1013-1019

Production Method 14

825-55-8

Reaction Conditions

1.1 Reagents: tert-Butyllithium Solvents: Tetrahydrofuran ;  3 h, 0 °C
1.2 Reagents: Zinc chloride ;  2 h, rt
1.3 Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ;  24 h, 55 °C

Reference

Synthesis of 2,5-Disubstituted Thienosultines and Their Thermal Reactions with Dienophiles and Nucleophiles

Liu, Wen-Dar; et al, Journal of Organic Chemistry, 2002, 67(26), 9267-9275

Production Method 15

825-55-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Dimethylacetamide

Reference

Palladium-catalyzed arylation of furan, thiophene, benzo[b]furan and benzo[b]thiophene

Ohta, Akihiro; et al, Heterocycles, 1990, 31(11), 1951-8

Production Method 16

98-80-6

1003-09-4

825-55-8

Reaction Conditions

1.1 Reagents: Potassium fluoride Catalysts: Palladium diacetate ,  9-(2′,6′-Dimethoxy[1,1′-biphenyl]-2-yl)-9-phosphabicyclo[3.3.1]nonane Solvents: Tetrahydrofuran ;  24 h, 25 °C

Reference

Evaluation of P-bridged biaryl phosphine ligands in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions

Lamola, Jairus L.; et al, RSC Advances, 2021, 11(43), 26883-26891

Production Method 17

98-80-6

1003-09-4

825-55-8

Reaction Conditions

1.1 Reagents: Sodium hydroxide ,  Tetrabutylammonium bromide ,  Oxygen Catalysts: Palladium ,  1,4-Benzenedicarbonyl dichloride, polymer with 1,4-benzenedicarboxamide Solvents: Water ;  1 h, 60 °C

Reference

Evaluation of Nitrogen-Based Polymeric Heterogeneous Catalysts for the Suzuki-Miyaura Cross-Coupling Reaction in Water

So, Jae Il ; et al, ACS Applied Polymer Materials, 2020, 2(8), 3122-3134

Production Method 18

3437-95-4

24388-23-6

825-55-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium Solvents: Methanol ;  1 h, 60 °C

Reference

Enhanced heterogeneously catalyzed Suzuki-Miyaura reaction over SiliaCat Pd(0)

Pandarus, Valerica; et al, Tetrahedron Letters, 2013, 54(35), 4712-4716

Production Method 19

591-50-4

54663-78-4

825-55-8

Reaction Conditions

1.1 Reagents: Sodium chloride Solvents: N-Methyl-2-pyrrolidone
1.2 Reagents: Manganese dibromide
1.3 Solvents: N-Methyl-2-pyrrolidone
1.4 Reagents: Potassium fluoride Solvents: Water

Reference

Copper- and Manganese-Catalyzed Cross-Coupling of Organostannanes with Organic Iodides in the Presence of Sodium Chloride

Kang, Suk-Ku; et al, Journal of Organic Chemistry, 1997, 62(13), 4208-4209

Production Method 20

591-50-4

54663-78-4

825-55-8

Reaction Conditions

1.1 Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ;  3 h, 85 °C

Reference

General facile synthesis of 2,5-diarylheteropentalenes

Vachal, Petr; et al, Tetrahedron Letters, 2004, 45(38), 7157-7161

Production Method 21

98-80-6

96-43-5

825-55-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: (SP-4-2)-[1,1′-Bis[bis(1,1-dimethylethyl)phosphino-κP]ferrocene]dichloropalladiu… Solvents: Acetonitrile ,  Water ;  2 h, 120 °C

Reference

A mild robust generic protocol for the Suzuki reaction using an air stable catalyst

Moseley, Jonathan D.; et al, Tetrahedron, 2012, 68(30), 6010-6017

Production Method 22

98-80-6

96-43-5

825-55-8

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: (SP-4-1)-[1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-yliden… Solvents: Ethanol ;  20 min, 25 °C

Reference

Effect on orthometallation of NHC palladium complexes toward the catalytic activity studies in Suzuki coupling reaction

Chen, Ming-Tsz; et al, Dalton Transactions, 2017, 46(47), 16394-16398

Production Method 23

1003-09-4

825-55-8

Reaction Conditions

1.1 Catalysts: Nickel(1+), chloro[N,N′-[6-(dimethylamino)-1,3,5-triazine-2,4-diyl-κN3]bis[P,P-b… Solvents: Tetrahydrofuran ;  rt; 6 h, 60 °C

Reference

A triazine-based Ni(II) PNP pincer complex as catalyst for Kumada-Corriu and Negishi cross-coupling reactions

Mastalir, Mathias; et al, Monatshefte fuer Chemie, 2017, 148(1), 105-109

Production Method 24

1003-09-4

2996-92-1

825-55-8

Reaction Conditions

1.1 Reagents: Sodium hydroxide Catalysts: Tetrabutylammonium bromide ,  Di-μ-chlorobis[5-chloro-2-[(4-chlorophenyl)(hydroxyimino-κN)methyl]phenyl-κC]dip… Solvents: Water ;  10 min, 120 °C

Reference

Solvent-less and fluoride-free Hiyama reaction of arylsiloxanes with aryl bromides and chlorides promoted by sodium hydroxide: a useful protocol for palladium recycling and product isolation

Alacid, Emilio; et al, Advanced Synthesis & Catalysis, 2006, 348, 945-952

Production Method 25

1003-09-4

2996-92-1

825-55-8

Reaction Conditions

1.1 Reagents: Potassium fluoride Catalysts: (SP-4-2)-Chloro[2-(9-phenyl-1,10-phenanthrolin-2-yl-κN1,κN10)phenyl-κC]palladium Solvents: (±)-Propylene glycol ,  Dichloromethane ;  12 h, 100 °C

Reference

The Hiyama Cross-Coupling Reaction at Parts Per Million Levels of Pd: In Situ Formation of Highly Active Spirosilicates in Glycol Solvents

Ichii, Shun; et al, Chemistry - An Asian Journal, 2019, 14(21), 3850-3854

Production Method 26

6165-68-0

825-55-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium(1+), [1-(diphenylphosphino-κP)-N-[(diphenylphosphino-κP)methyl]methana… (ArgoGel bound) Solvents: Water

Reference

An Amphiphilic Resin-Supported Palladium Catalyst for High-Throughput Cross-Coupling in Water

Uozumi, Yasuhiro; et al, Organic Letters, 2002, 4(17), 2997-3000

Production Method 27

591-50-4

825-55-8

Reaction Conditions

1.1 Reagents: Silver carbonate Catalysts: Tricyclohexylphosphine ,  Palladium chloride Solvents: m-Xylene ;  12 h, 130 °C

Reference

A General Catalyst for the β-Selective C-H Bond Arylation of Thiophenes with Iodoarenes

Ueda, Kirika; et al, Angewandte Chemie, 2010, 49(47), 8946-8949

Production Method 28

591-50-4

825-55-8

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  -78 °C; -78 °C → 0 °C; 1 h, 0 °C; 0 °C → -40 °C
1.2 Reagents: Zinc chloride Solvents: Tetrahydrofuran ;  15 min, -40 °C
1.3 Catalysts: Tris(2-furyl)phosphine ,  Tris(dibenzylideneacetone)dipalladium Solvents: Tetrahydrofuran ;  45 min, 100 °C
1.4 Reagents: Ammonium chloride Solvents: Water

Reference

Application of the Negishi reaction in the synthesis of thiophene-based lignans analogues with leishmanicidal effects

Amaral, Monica F. Z. J.; et al, Journal of the Brazilian Chemical Society, 2014, 25(10), 1907-1913

Production Method 29

591-50-4

825-55-8

Reaction Conditions

1.1 Reagents: Butyllithium ,  Magnesium bromide Solvents: Tetrahydrofuran ;  1 h, -10 °C
1.2 2 h, rt
1.3 Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium ;  18 h, reflux
1.4 Reagents: Ammonium chloride Solvents: Water

Reference

Deprotonation of thiophenes using lithium magnesates

Bayh, Omar; et al, Tetrahedron, 2005, 61(20), 4779-4784

Production Method 30

591-50-4

6165-68-0

825-55-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium(1+), [1-(diphenylphosphino-κP)-N-[(diphenylphosphino-κP)methyl]methana… (ArgoGel bound) Solvents: Water

Reference

An Amphiphilic Resin-Supported Palladium Catalyst for High-Throughput Cross-Coupling in Water

Uozumi, Yasuhiro; et al, Organic Letters, 2002, 4(17), 2997-3000

Production Method 31

591-50-4

6165-68-0

825-55-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium ,  Chitosan, N-(aminothioxomethyl) Solvents: Water ;  14 h, 80 °C

Reference

Palladium nanoparticles embedded on thiourea-modified chitosan: a green and sustainable heterogeneous catalyst for the Suzuki reaction in water

Affrose, Abdullah; et al, RSC Advances, 2015, 5(35), 27533-27539

2-Phenylthiophene Raw materials

• Phenylboronic acid
• 2-Iodothiophene
• Iodobenzene
• 3-Iodothiophene
• 2-(Tributylstannyl)thiophene
• 2-Bromothiophene
• 2-Chlorothiophene
• Thiophene-2-boronic acid
• Phenyltrimethoxysilane
• Phenylboronic Acid Pinacol Ester

2-Phenylthiophene Preparation Products

• 2-Phenylthiophene (825-55-8)

• 1. An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning?
  Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao Duan Nanoscale, 2016,8, 19541-19550
• 2. An artificial photosynthesis system comprising a covalent triazine framework as an electron relay facilitator for photochemical carbon dioxide reduction?
  Siquan Zhang,Shengyao Wang,Liping Guo,Hao Chen,Bien Tan,Shangbin Jin J. Mater. Chem. C, 2020,8, 192-200
• 3. An investigation of surface properties, local elastic modulus and interaction with simulated pulmonary surfactant of surface modified inhalable voriconazole dry powders using atomic force microscopy
  Michael Kappl,Paul M. Young,Daniela Traini,Sanyog Jain RSC Adv., 2016,6, 25789-25798
• 4. Aluminium complexes with thio-phosphorus ligands: syntheses and characterisations of [Al2(CyPS3)2(CyPHS2)2] and [Al(S2PPh2)3]?
  Robert P. Davies,Maria A. Giménez,Laura Patel,Andrew J. P. White Dalton Trans., 2008, 5705-5707
• 5. An approach to biodegradable star polymeric architectures using disulfide coupling?
  Jingquan Liu,Huiyun Liu,Zhongfan Jia,Volga Bulmus,Thomas P. Davis Chem. Commun., 2008, 6582-6584

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzene and substituted derivatives
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives

• 85553-43-1(2-(3-Methylphenyl)thiophene)
• 104500-00-7(Thiophene,2,2'-(1,3-phenylene)bis-)
• 23354-94-1(2-(4-(Thien-2-yl)phenyl)thiophene)
• 56316-86-0(2,5-Bis(4-biphenylyl)thiophene)
• 5069-26-1(2-Methyl-5-phenylthiophene)
• 16939-04-1(2-P-Tolylthiophene)
• 82366-98-1(Thiophene, 2,5-bis(4-methylphenyl)-)
• 15509-95-2(1,3,5-Tri(2-thienyl)benzene)
• 1445-78-9(2,5-Diphenylthiophene)
• 109359-51-5(2-[4-(4-thiophen-2-ylphenyl)phenyl]thiophene)