Production Method 1

2051-60-7

73183-34-3

914675-52-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Tris(dibenzylideneacetone)dipalladium ,  X-Phos Solvents: Polyethylene glycol (PEG-2000) ;  rt → 50 °C
1.2 6 h, 110 °C

Reference

Recyclable Pd2dba3/XPhos/PEG-2000 System for Efficient Borylation of Aryl Chlorides: Practical Access to Aryl Boronates

Cai, Mingzhong ; et al, Synthesis, 2022, 54(5), 1339-1346

Production Method 2

76-09-5

4688-76-0

914675-52-8

Reaction Conditions

1.1 Solvents: Diethyl ether ;  18 h, rt

Reference

Hydrogenation of (Hetero)aryl Boronate Esters with a Cyclic (Alkyl)(amino)carbene-Rhodium Complex: Direct Access to cis-Substituted Borylated Cycloalkanes and Saturated Heterocycles

Ling, Liang; et al, Angewandte Chemie, 2019, 58(20), 6554-6558

Production Method 3

159087-45-3

53097-28-2

914675-52-8

Reaction Conditions

1.1 Catalysts: Zinc ,  Zinc iodide ,  (T-4)-Dibromo[1,1′-(1,2-ethanediyl)bis[1,1-diphenylphosphine-κP]]cobalt Solvents: Dichloromethane ;  16 h, rt

Reference

Ambient-Temperature Cobalt-Catalyzed Cycloaddition Strategies to Aromatic Boronic Esters

Auvinet, Anne-Laure; et al, Journal of Organic Chemistry, 2010, 75(11), 3893-3896

Production Method 4

2052-07-5

25015-63-8

914675-52-8

Reaction Conditions

1.1 Catalysts: Tris(dibenzylideneacetone)dipalladium ,  1,1′-(Oxydi-2,1-phenylene)bis[1,1-bis(1,1-dimethylethyl)phosphine Solvents: 1,4-Dioxane ;  rt; 30 min, rt
1.2 Reagents: Triethylamine ;  rt; 6 h, 100 °C

Reference

An efficient catalyst system for palladium-catalyzed borylation of aryl halides with pinacolborane

Murata, Miki; et al, Synlett, 2006, (12), 1867-1870

Production Method 5

2052-07-5

1644277-86-0

914675-52-8

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Tetrahydrofuran ;  5 min, 25 °C; 3 h, 25 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  5 min, 25 °C

Reference

Preparation and reactions of 4-iodobutyl pinacolborate. Synthesis of substituted alkyl and aryl pinacolboronates via 4-iodobutyl pinacolborate utilizing tetrahydrofuran as the leaving group

Murphy, Chris L.; et al, Tetrahedron Letters, 2015, 56(23), 3032-3033

Production Method 6

73183-34-3

321-60-8

914675-52-8

Reaction Conditions

1.1 Reagents: Cesium fluoride Catalysts: Bis(1,5-cyclooctadiene)nickel ,  Tricyclohexylphosphine ,  Cuprous iodide Solvents: Toluene ;  1 min, rt; 24 h, 80 °C

Reference

Ni/Cu-Catalyzed Defluoroborylation of Fluoroarenes for Diverse C-F Bond Functionalizations

Niwa, Takashi; et al, Journal of the American Chemical Society, 2015, 137(45), 14313-14318

Production Method 7

73183-34-3

19813-75-3

914675-52-8

Reaction Conditions

1.1 Catalysts: Tricyclohexylphosphine ,  Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-hydroxydirhodium Solvents: Hexane ;  1 h, 80 °C; 80 °C → rt
1.2 Solvents: Hexane ;  12 h, 80 °C

Reference

Rhodium-catalyzed ipso-borylation of alkylthioarenes via C-S bond cleavage

Uetake, Yuta; et al, Organic Letters, 2016, 18(11), 2758-2761

Production Method 8

73183-34-3

914675-52-8

Reaction Conditions

1.1 Catalysts: Triphenylphosphine ,  Bis(1,5-cyclooctadiene)nickel Solvents: Toluene ,  Octane ;  30 s, rt
1.2 Reagents: Sodium chloride ,  Potassium fluoride ;  24 h, 140 °C

Reference

Nickel-catalyzed decarbonylative borylation of aroyl fluorides

Wang, Zhenhua; et al, Chemical Communications (Cambridge, 2018, 54(99), 13969-13972

Production Method 9

73183-34-3

914675-52-8

Reaction Conditions

1.1 Catalysts: (SP-4-1)-Fluorophenylbis(tricyclohexylphosphine)nickel Solvents: Toluene ;  16 h, 115 °C

Reference

Mechanism and Scope of Nickel-Catalyzed Decarbonylative Borylation of Carboxylic Acid Fluorides

Malapit, Christian A. ; et al, Journal of the American Chemical Society, 2019, 141(43), 17322-17330

Production Method 10

159087-45-3

914675-52-8

Reaction Conditions

1.1 Catalysts: Zinc ,  Zinc iodide ,  (T-4)-Dibromo[1,1′-(1,2-ethanediyl)bis[1,1-diphenylphosphine-κP]]cobalt Solvents: Dichloromethane ;  4 h, rt
1.2 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Benzene ;  1 h, rt

Reference

Ambient-Temperature Cobalt-Catalyzed Cycloaddition Strategies to Aromatic Boronic Esters

Auvinet, Anne-Laure; et al, Journal of Organic Chemistry, 2010, 75(11), 3893-3896

Production Method 11

73183-34-3

914675-52-8

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Catalysts: Bis(acetylacetonato)nickel ,  1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dimethyl-, chloride (1… Solvents: Cyclopentyl methyl ether ;  16 h, 100 °C

Reference

Nickel-Catalyzed Ipso-Borylation of Silyloxyarenes via C-O Bond Activation

Pein, Wesley L. ; et al, Organic Letters, 2021, 23(12), 4588-4592

Production Method 12

25015-63-8

321-60-8

914675-52-8

Reaction Conditions

1.1 Reagents: Magnesium Catalysts: Cobalt chloride (CoCl2) ,  2,4,6-Trimethyl-N-[1-methyl-3-[(2,4,6-trimethylphenyl)amino]-2-buten-1-ylidene]b… Solvents: Tetrahydrofuran ;  16 h, 60 °C; 60 °C → rt
1.2 Reagents: Water ;  rt

Reference

Cobalt-Catalyzed C-F Bond Borylation of Aryl Fluorides

Lim, Soobin; et al, Organic Letters, 2018, 20(22), 7249-7252

Production Method 13

2051-60-7

73183-34-3

914675-52-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Palladium diacetate ,  Silica Solvents: Benzene ;  10 h, 60 °C

Reference

Palladium-Catalyzed Borylation of Sterically Demanding Aryl Halides with a Silica-Supported Compact Phosphane Ligand

Kawamorita, Soichiro; et al, Angewandte Chemie, 2011, 50(36), 8363-8366

Production Method 14

2051-60-7

73183-34-3

914675-52-8

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: Chloro(1,3-dicyclohexyl-1,3-dihydro-2H-imidazol-2-ylidene)copper Solvents: Methylcyclohexane ;  42 h, 100 °C

Reference

Copper-catalysed borylation of aryl chlorides

Kuehn, Laura; et al, Organic & Biomolecular Chemistry, 2019, 17(27), 6601-6606

Production Method 15

76-09-5

4688-76-0

914675-52-8

Reaction Conditions

1.1 Reagents: Acetic acid ,  Sodium sulfate Solvents: Tetrahydrofuran ;  2 d, 20 °C

Reference

Bright Luminescent Platinum(II)-Biaryl Emitters Synthesized Without Air-Sensitive Reagents

Wakasugi, Chuei; et al, Chemistry - A European Journal, 2020, 26(24), 5449-5458

Production Method 16

2052-07-5

25015-63-8

914675-52-8

Reaction Conditions

1.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  3 h, 25 °C
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Hydride as a Leaving Group in the Reaction of Pinacolborane with Halides under Ambient Grignard and Barbier Conditions. One-Pot Synthesis of Alkyl, Aryl, Heteroaryl, Vinyl, and Allyl Pinacolboronic Esters

Clary, Jacob W.; et al, Journal of Organic Chemistry, 2011, 76(23), 9602-9610

Production Method 17

73183-34-3

321-60-8

914675-52-8

Reaction Conditions

1.1 Reagents: Cesium fluoride Catalysts: Chlorobis(tricyclohexylphosphine)copper Solvents: Toluene ;  24 h, 80 °C

Reference

Copper-Catalyzed ipso-Borylation of Fluoroarenes

Niwa, Takashi ; et al, ACS Catalysis, 2017, 7(7), 4535-4541

Production Method 18

73183-34-3

19813-75-3

914675-52-8

Reaction Conditions

1.1 Reagents: Lithium bis(trimethylsilyl)amide Catalysts: (SP-4-1)-[1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-yliden… Solvents: Tetrahydrofuran ;  15 h, 80 °C; 80 °C → rt
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Palladium-Catalyzed ipso-Borylation of Aryl Sulfides with Diborons

Bhanuchandra, M.; et al, Organic Letters, 2016, 18(12), 2966-2969

Production Method 19

73183-34-3

914675-52-8

Reaction Conditions

1.1 Reagents: Tripotassium phosphate ,  Methanaminium, N-[(dimethylamino)fluoromethylene]-N-methyl-, hexafluorophosphate… Catalysts: Bis(1,5-cyclooctadiene)nickel ,  Tricyclohexylphosphine Solvents: 1,4-Dioxane ;  24 h, 60 °C

Reference

Ni-Catalyzed Deoxygenative Borylation of Phenols Via O-Phenyl-uronium Activation

Liu, Xiaojie; et al, ACS Catalysis, 2022, 12(15), 8904-8910

Production Method 20

73183-34-3

947-84-2

914675-52-8

Reaction Conditions

1.1 Reagents: Triethylamine ,  Pivalic anhydride Catalysts: Palladium diacetate ,  1,4-Bis(diphenylphosphino)butane Solvents: 1,4-Dioxane ;  rt; 15 h, 160 °C

Reference

Palladium-Catalyzed Decarbonylative Borylation of Carboxylic Acids: Tuning Reaction Selectivity by Computation

Liu, Chengwei; et al, Angewandte Chemie, 2018, 57(51), 16721-16726

Production Method 21

73183-34-3

914675-52-8

Reaction Conditions

1.1 Reagents: Lithium carbonate (Li2CO3) Catalysts: Tributylphosphine ,  Bis(1,5-cyclooctadiene)nickel Solvents: 1,4-Dioxane ;  72 h, 170 °C

Reference

Functional Group Interconversion: Decarbonylative Borylation of Esters for the Synthesis of Organoboronates

Guo, Lin; et al, Chemistry - A European Journal, 2016, 22(47), 16787-16790

Production Method 22

73183-34-3

914675-52-8

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Catalysts: Bis(acetylacetonato)nickel ,  1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dimethyl-, chloride (1… Solvents: Cyclopentyl methyl ether ;  16 h, 100 °C

Reference

Nickel-catalyzed ipso-borylation of silyloxyarenes via C-O bond activation

Pein, Wesley L.; et al, ChemRxiv, 2021, 1, 1-6

4,4,5,5-tetramethyl-2-(2-phenylphenyl)-1,3,2-dioxaborolane Raw materials

• 2,3-Dimethylbutane-2,3-diol
• 4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane
• 2-Bromo-1,1'-biphenyl
• 2-Chlorobiphenyl
• Bis(pinacolato)diborane
• Pinacolborane
• 2-Phenylbenzoic acid
• 2-Fluorobiphenyl
• [1,1'-biphenyl]-2-ylboronic acid
• BENZENE, (1,3-BUTADIENYLTHIO)-
• 1,3,2-Dioxaborolane, 2-(4-iodobutoxy)-4,4,5,5-tetramethyl-
• 1,1'-Biphenyl, 2-(methylthio)-

4,4,5,5-tetramethyl-2-(2-phenylphenyl)-1,3,2-dioxaborolane Preparation Products

• 4,4,5,5-tetramethyl-2-(2-phenylphenyl)-1,3,2-dioxaborolane (914675-52-8)

• 1. Excellent mechanical performance and enhanced dielectric properties of OBC/SiO2 elastomeric nanocomposites: effect of dispersion of the SiO2 nanoparticles?
  Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei Yang RSC Adv., 2017,7, 46297-46305
• 2. Evidence for the intrinsic nature of band-gap states electrochemically observed on atomically flat TiO2(110) surfaces?
  Shintaro Takata,Yoshihiro Miura Phys. Chem. Chem. Phys., 2014,16, 24784-24789
• 3. Fe3O4 nanosphere@microporous organic networks: enhanced anode performances in lithium ion batteries through carbonization?
  Byungho Lim,Jaewon Jin,Jin Yoo,Seung Yong Han,Kyeongyeol Kim,Sungah Kang,Nojin Park,Sang Moon Lee,Hae Jin Kim,Seung Uk Son Chem. Commun., 2014,50, 7723-7726
• 4. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
  Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341
• 5. Fe3O4/PEG-SO3H as a heterogeneous and magnetically-recyclable nanocatalyst for the oxidation of sulfides to sulfones or sulfoxides
  Saeideh Mirfakhraei,Malak Hekmati,Fereshteh Hosseini Eshbala,Hojat Veisi New J. Chem., 2018,42, 1757-1761

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

• 195062-59-0(4,4,5,5-Tetramethyl-2-(o-tolyl)-1,3,2-dioxaborolane)
• 356570-53-1(2-(2,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 398128-09-1(2,2'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)biphenyl)
• 583823-92-1(1,3,2-DIOXABOROLANE, 4,4,5,5-TETRAMETHYL-2-[1,1':3',1''-TERPHENYL]-4'-YL-)
• 214360-64-2(2-(2,4-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-Dioxaborolane)
• 1062555-59-2(4,4,5,5-Tetramethyl-2-(2-(naphthalen-2-yl)phenyl)-1,3,2-dioxaborolane)
• 171364-84-4(4,4,5,5-Tetramethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborolane)
• 325141-72-8(2-(2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 612086-25-6(1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(2-phenyl-1-naphthalenyl)-)
• 303006-89-5(2,5-Dimethyl-1,4-phenylenediboronic acid, pinacol ester)