Production Method 1

88-15-3

25015-63-8

942070-32-8

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: Hexane ;  1 min, rt
1.2 30 min, rt

Reference

Iridium-catalyzed borylation of thiophenes: versatile, synthetic elaboration founded on selective C-H functionalization

Chotana, Ghayoor A.; Kallepalli, Venkata A.; Maleczka, Robert E. Jr.; Smith, Milton R. III, Tetrahedron, 2008, 64(26), 6103-6114

Production Method 2

6310-09-4

73183-34-3

942070-32-8

Reaction Conditions

1.1 Reagents: Diisopropylethylamine ,  Oxygen ,  1,1-Dimethylethyl N-[(1S)-4-(octadecylamino)-1-[(octadecylamino)carbonyl]-4-oxob… Solvents: Acetonitrile ,  Water ;  1.5 min, rt → 150 °C; 150 °C → rt; 2 h, 23 °C
1.2 Reagents: Sodium chloride Solvents: Water

Reference

Aerobic Visible-Light-Driven Borylation of Heteroarenes in a Gel Nanoreactor

Herrera-Luna, Jorge C. ; Diaz Diaz, David; Abramov, Alex; Encinas, Susana; Jimenez, M. Consuelo; et al, Organic Letters, 2021, 23(6), 2320-2325

Production Method 3

73183-34-3

5370-25-2

942070-32-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Tris(dibenzylideneacetone)dipalladium ,  X-Phos Solvents: Toluene ;  rt → 120 °C; 4 h, 120 °C

Reference

Imide sulfonate photoacid generator with high yield of acid, composition and application thereof

, China, , ,

Production Method 4

73183-34-3

5370-25-2

942070-32-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: Dimethyl sulfoxide ,  1,4-Dioxane ;  1 h, 90 °C

Reference

Preparation of pyrimidine compounds as tuberculosis inhibitors

, World Intellectual Property Organization, , ,

Production Method 5

76-09-5

206551-43-1

942070-32-8

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  < 1 atm, 40 °C

Reference

Stereocomplementary asymmetric bioreduction of boron-containing ketones mediated by alcohol dehydrogenases

Barcellos, Thiago; Tauber, Katharina; Kroutil, Wolfgang; Andrade, Leandro H., Tetrahedron: Asymmetry, 2011, 22(18-19), 1772-1777

Production Method 6

88-15-3

73183-34-3

942070-32-8

Reaction Conditions

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium ,  5-Methyl-2-(3-thienyl)pyridine Solvents: Tetrahydrofuran ;  2 min, rt
1.2 12 h, 80 °C

Reference

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Hoque, Emdadul Md; Hassan, Mirja Mahamudul Md; Chattopadhyay, Buddhadeb, Journal of the American Chemical Society, 2021, 143(13), 5022-5037

Production Method 7

88-15-3

73183-34-3

942070-32-8

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Isopropanol ,  Chloro[(1,2,5,6-η)-1,5-cyclooctadiene](1,10-phenanthroline-κN1,κN10)iridium Solvents: Heptane ;  1 h, 75 °C
1.2 18 h

Reference

Understanding the Activation of Air-Stable Ir(COD)(Phen)Cl Precatalyst for C-H Borylation of Aromatics and Heteroaromatics

Slack, Eric D.; Colacot, Thomas J., Organic Letters, 2021, 23(5), 1561-1565

Production Method 8

73183-34-3

128327-59-3

942070-32-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  2 h, rt → 90 °C

Reference

3-(3H-Imidazo[4,5-c]pyridin-2-yl)-1H-pyrazolo[4,3-b]pyridines as Wnt pathway modulators and their preparation

, World Intellectual Property Organization, , ,

Production Method 9

6310-09-4

73183-34-3

942070-32-8

88-15-3

Reaction Conditions

1.1 Reagents: Dodecanenitrile ,  Diisopropylethylamine Solvents: Acetonitrile ,  Water ;  30 min, 1 atm, 23 °C

Reference

Rapid Access to Borylated Thiophenes Enabled by Visible Light

Herrera-Luna, Jorge C.; Sampedro, Diego ; Jimenez, M. Consuelo; Perez-Ruiz, Raul, Organic Letters, 2020, 22(8), 3273-3278

1-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)ethanone Raw materials

• 2,3-Dimethylbutane-2,3-diol
• (5-acetylthiophen-2-yl)boronic acid
• 2-Acetylthiophene
• 2-Acetyl-5-chlorothiophene
• Bis(pinacolato)diborane
• Pinacolborane
• 1-(5-bromothiophen-2-yl)ethan-1-one
• Ethanone,1-(5-amino-2-thienyl)-

1-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)ethanone Preparation Products

• 2-Acetylthiophene (88-15-3)
• 1-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)ethanone (942070-32-8)

• 1. Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties
  Huabin Zhang,Shaowu Du CrystEngComm, 2014,16, 4059-4068
• 2. Aggregation-induced chiral symmetry breaking of a naphthalimide–cyanostilbene dyad?
  Xin Li,Liangliang Zhu,Sai Duan,Yanli Zhao,Hans ?gren Phys. Chem. Chem. Phys., 2014,16, 23854-23860
• 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 analyte-triggered artificial peroxidase system based on dimanganese complex for a versatile enzyme assay?
  Suji Lee,Min Su Han Chem. Commun., 2021,57, 9450-9453
• 5. Aluminium alkyl and aryloxide complexes of pyrazine and bipyridines: synthesis and structure?
  Doug Ogrin,Laura H. van Poppel,Simon G. Bott,Andrew R. Barron Dalton Trans., 2004, 3689-3694

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ketones
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Ketones

• 1040281-83-1(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde)
• 1447710-10-2(5-Ethylthiophene-2-boronic acid pinacol ester)
• 1402166-55-5(2-(5-cyclohexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 925424-90-4(4,4,5,5-Tetramethyl-2-(5-octyl-2-thienyl)-1,3,2-dioxaborolane)
• 2223044-83-3(2-(5-cyclopentylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 1390584-88-9(2-[5-(2-Ethylhexyl)thiophen-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 1473358-18-7(5-N-Propylthiophene-2-Boronic Acid Pinacol Este)
• 1338083-26-3(2-(5-Butylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 917985-54-7(2-(5-hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 476004-80-5(4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane)