Production Method 1

76-09-5

942070-28-2

885692-91-1

635305-48-5

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium ,  1H-Imidazolium, 1,3-dicyclohexyl-, chloride (1:1) Solvents: Methylcyclohexane ;  5 min, rt
1.2 Reagents: N,N-Bis(1-methylethyl)boranamine ;  4 h, 110 °C; 110 °C → rt
1.3 Solvents: Tetrahydrofuran ;  1.5 h, rt

Reference

Iridium/N-heterocyclic carbene-catalyzed C-H borylation of arenes by diisopropylaminoborane

Tobisu, Mamoru; Igarashi, Takuya; Chatani, Naoto, Beilstein Journal of Organic Chemistry, 2016, 12, 654-661

Production Method 2

73183-34-3

942070-28-2

885692-91-1

635305-48-5

Reaction Conditions

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Solvents: Tetrahydrofuran ;  15 - 30 min, rt
1.2 rt; 25 h, 65 °C

Reference

Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand

Karmel, Caleb; Rubel, Camille Z.; Kharitonova, Elena V.; Hartwig, John F., Angewandte Chemie, 2020, 59(15), 6074-6081

Production Method 3

73183-34-3

942070-28-2

885692-91-1

635305-48-5

Reaction Conditions

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Solvents: Tetrahydrofuran ;  15 - 30 min, rt
1.2 25 h, 65 °C

Reference

Iridium-catalyzed silylation of five-membered heteroarenes: high sterically derived selectivity from a pyridyl-imidazoline ligand

Karmel, Caleb; Rubel, Camille Z.; Kharitonova, Elena V.; Hartwig, John F., ChemRxiv, 2019, 1, 1-10

2,2'-(3-Methylthiophene-2,5-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) Raw materials

• 2,3-Dimethylbutane-2,3-diol
• Bis(pinacolato)diborane

2,2'-(3-Methylthiophene-2,5-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) Preparation Products

• 4,4,5,5-Tetramethyl-2-(3-methylthiophen-2-yl)-1,3,2-dioxaborolane (885692-91-1)
• 4,4,5,5-Tetramethyl-2-(4-methylthiophen-2-yl)-1,3,2-dioxaborolane (635305-48-5)
• 2,2'-(3-Methylthiophene-2,5-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (942070-28-2)

• 1. Emergence of cationic polyamine dendrimersomes: design, stimuli sensitivity and potential biomedical applications
  Partha Laskar,Christine Dufès Nanoscale Adv., 2021,3, 6007-6026
• 2. Emerging 2D hybrid nanomaterials: towards enhanced sensitive and selective conductometric gas sensors at room temperature
  Hanie Hashtroudi,Ian D. R. Mackinnon J. Mater. Chem. C, 2020,8, 13108-13126
• 3. Excitable dynamics in the bromate–sulfite–ferrocyanide reaction
  J. Zagora,M. Vosla?,L. Schreiberová,I. Schreiber Phys. Chem. Chem. Phys., 2002,4, 1284-1291
• 4. Esterase-responsive polymeric prodrug-based tumor targeting nanoparticles for improved anti-tumor performance against colon cancer?
  Gang Pan,Yi-jie Bao,Jie Xu,Tao Liu,Cheng Liu,Yan-yan Qiu,Xiao-jing Shi,Hui Yu,Ting-ting Jia,Xia Yuan,Ze-ting Yuan,Yi-jun Cao RSC Adv., 2016,6, 42109-42119
• 5. Evolution of calcium phosphate precipitation in hanging drop vapor diffusion by in situRaman microspectroscopy
  Gloria Belén Ramírez-Rodríguez,José Manuel Delgado-López,Jaime Gómez-Morales CrystEngComm, 2013,15, 2206-2212

• 885692-91-1(4,4,5,5-Tetramethyl-2-(3-methylthiophen-2-yl)-1,3,2-dioxaborolane)
• 1310384-43-0((2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-yl)methanol)
• 635305-48-5(4,4,5,5-Tetramethyl-2-(4-methylthiophen-2-yl)-1,3,2-dioxaborolane)
• 960524-18-9(3-Dodecyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene)
• 463336-26-7(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carbonitrile)
• 960116-25-0(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-4-phenylthiophene)
• 850881-09-3(2-(3-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 1174910-80-5(2-(3-(2-Ethylhexyl)thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 916454-58-5(3-Thiophenecarbonitrile,2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-)
• 632325-55-4(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carbaldehyde)