Production Method 1

1121-86-4

73183-34-3

936618-92-7

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: Diethylzinc Solvents: Tetrahydrofuran ,  Hexane ;  0 °C; 30 min, rt
1.2 rt → 75 °C; 24 h, 75 °C
1.3 Reagents: Ammonium chloride Solvents: Water

Reference

Design, Generation, and Synthetic Application of Borylzincate: Borylation of Aryl Halides and Borylzincation of Benzynes/Terminal Alkyne

Nagashima, Yuki; Takita, Ryo; Yoshida, Kengo; Hirano, Keiichi; Uchiyama, Masanobu, Journal of the American Chemical Society, 2013, 135(50), 18730-18733

Production Method 2

1073-06-9

73183-34-3

936618-92-7

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: Phenothiazine Solvents: Acetonitrile ;  48 h

Reference

Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds

Jin, Shengfei; Dang, Hang. T.; Haug, Graham C.; He, Ru; Nguyen, Viet D.; et al, Journal of the American Chemical Society, 2020, 142(3), 1603-1613

Production Method 3

73183-34-3

936618-92-7

Reaction Conditions

1.1 Reagents: Sodium oxalate ,  Tripotassium phosphate Catalysts: 4-Cyanopyridine ,  2,4,5-Tri-9H-carbazol-9-yl-6-(ethylphenylamino)-1,3-benzenedicarbonitrile Solvents: Acetonitrile ;  24 h, rt
1.2 Reagents: Ammonium chloride Solvents: Ethyl acetate ,  Water ;  rt

Reference

Unveiling Extreme Photoreduction Potentials of Donor-Acceptor Cyanoarenes to Access Aryl Radicals from Aryl Chlorides

Xu, Jinhui ; Cao, Jilei; Wu, Xiangyang; Wang, Han; Yang, Xiaona; et al, Journal of the American Chemical Society, 2021, 143(33), 13266-13273

Production Method 4

76-09-5

14874-70-5

20460-04-2

936618-92-7

Reaction Conditions

1.1 Reagents: N,N-Bis(1-methylethyl)boranamine Catalysts: Ferrocene Solvents: Acetonitrile ;  2.5 h, rt
1.2 Reagents: Methanol ;  0 °C; 1 h, rt
1.3 Solvents: Diethyl ether ;  4 h, rt

Reference

Iron-Catalyzed Borylation of Arenediazonium Salts to Give Access to Arylboron Derivatives via Aryl(amino)boranes at Room Temperature

Marciasini, Ludovic D.; Richy, Nicolas; Vaultier, Michel; Pucheault, Mathieu, Advanced Synthesis & Catalysis, 2013, 355(6), 1083-1088

Production Method 5

1073-06-9

73183-34-3

936618-92-7

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  17 h, 100 °C

Reference

Effect of conjugated small molecular electrolytes based on carbazole with N and F atoms for the automatic formation of electron transport layer in polymer solar cell

Kim, Juae; Kim, Yong Ryun; Kim, Minji; Yoon, Chang Jae; Piao, Junying; et al, Synthetic Metals, 2021, 275,

Production Method 6

73183-34-3

936618-92-7

Reaction Conditions

1.1 Reagents: tert-Butyl nitrite Solvents: Acetonitrile

Reference

Direct synthesis of arylboronic pinacol esters from arylamines

Qiu, Di; Zhang, Yan; Wang, Jianbo, Organic Chemistry Frontiers, 2014, 1(4), 422-425

Production Method 7

73183-34-3

936618-92-7

Reaction Conditions

1.1 Reagents: tert-Butyl nitrite Solvents: Acetonitrile ;  2 h, 80 °C

Reference

Synthesis of Pinacol Arylboronates from Aromatic Amines: A Metal-Free Transformation

Qiu, Di; Jin, Liang; Zheng, Zhitong; Meng, He; Mo, Fanyang; et al, Journal of Organic Chemistry, 2013, 78(5), 1923-1933

Production Method 8

1073-06-9

73183-34-3

936618-92-7

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: Dimethyl sulfoxide ;  48 h, 80 °C

Reference

Group 4 Post-Metallocenes Supported by [OCH2N,C(σ-aryl)] Auxiliaries Bearing a Seven-Membered Metallacycle: Synthesis, Characterization, and Catalysts for Olefin Polymerization

Liu, Cham-Chuen; Liu, Qian; Yiu, Shek-Man; Chan, Michael C. W., Organometallics, 2019, 38(15), 2963-2971

Production Method 9

73183-34-3

936618-92-7

863868-36-4

Reaction Conditions

1.1 Reagents: Cesium fluoride Catalysts: Bis[1,3-dihydro-1,3-bis(2,4,6-trimethylphenyl)-2H-imidazol-2-ylidene]nickel ,  1960399-43-2 Solvents: Mesitylene ;  6 h, 25 °C

Reference

Selective Photocatalytic C-F Borylation of Polyfluoroarenes by Rh/Ni Dual Catalysis Providing Valuable Fluorinated Arylboronate Esters

Tian, Ya-Ming; et al, Journal of the American Chemical Society, 2018, 140(50), 17612-17623

Production Method 10

73183-34-3

936618-92-7

Reaction Conditions

1.1 Reagents: Sodium oxalate ,  4-Cyanopyridine ,  Tripotassium phosphate Catalysts: 2,4,5-Tri-9H-carbazol-9-yl-6-(ethylphenylamino)-1,3-benzenedicarbonitrile Solvents: Acetonitrile ;  24 h, rt
1.2 Reagents: Ammonium chloride Solvents: Ethyl acetate ,  Water

Reference

Unveiling extreme photoreduction potentials of donor-acceptor cyanoarenes to access aryl radicals from aryl chlorides

Xu, Jinhui; Cao, Jilei; Wu, Xiangyang; Wang, Han; Yang, Xiaona; et al, ChemRxiv, 2021, 1, 1-7

Production Method 11

1121-86-4

73183-34-3

936618-92-7

Reaction Conditions

1.1 Reagents: Pyridine ,  Cesium fluoride Solvents: Dimethyl sulfoxide ;  rt → 105 °C; 2 h, 105 °C

Reference

Radical Metal-Free Borylation of Aryl Iodides

Pinet, Sandra; Liautard, Virginie; Debiais, Megane; Pucheault, Mathieu, Synthesis, 2017, 49(21), 4759-4768

Production Method 12

557087-01-1

1073-06-9

936618-92-7

Reaction Conditions

1.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  rt → 45 °C
1.2 Solvents: Tetrahydrofuran ;  45 °C; 5 h, 45 °C
1.3 Solvents: Tetrahydrofuran ;  0 - 5 °C; 1 h, 0 - 5 °C; 5 °C → rt; 2 h, rt
1.4 Reagents: Sodium chloride Solvents: Water

Reference

Novel boronizing reagent pinacolyl dimethylamino-borate, and the preparation method and application thereof

, China, , ,

Production Method 13

76-09-5

14874-70-5

20460-04-2

936618-92-7

Reaction Conditions

1.1 Reagents: N,N-Bis(1-methylethyl)boranamine Catalysts: Ferrocene Solvents: Acetonitrile ;  2.5 h, rt
1.2 Reagents: Methanol ;  0 °C; 1 h, rt
1.3 Solvents: Diethyl ether ;  4 h, rt

Reference

New process for preparing arylboranes, arylboronates and MIDA-borates by arylation of organoboron compounds with aryldiazonium salts

, World Intellectual Property Organization, , ,

Production Method 14

76-09-5

14874-70-5

20460-04-2

936618-92-7

Reaction Conditions

1.1 Reagents: N,N-Bis(1-methylethyl)boranamine Catalysts: Ferrocene Solvents: Acetonitrile ;  2.5 h, rt
1.2 Reagents: Methanol ;  0 °C; 1 h, rt
1.3 Solvents: Diethyl ether ;  4 h, rt

Reference

New process for preparing arylboranes by arylation of organoboron compounds

, European Patent Organization, , ,

Production Method 15

1121-86-4

73183-34-3

936618-92-7

Reaction Conditions

1.1 Catalysts: Bis(dimethylamino)methane Solvents: Acetone ,  Acetonitrile ,  Water ;  15 min, -5 °C

Reference

Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions

Chen, Kai; Zhang, Shuai; He, Pei; Li, Pengfei, Chemical Science, 2016, 7(6), 3676-3680

Production Method 16

76-09-5

14874-70-5

20460-04-2

936618-92-7

Reaction Conditions

1.1 Reagents: N,N-Bis(1-methylethyl)boranamine Catalysts: Titanocene dichloride Solvents: Acetonitrile ;  2 h, rt
1.2 Solvents: Methanol ;  0 °C; 1 h, rt
1.3 Solvents: Diethyl ether ;  4 h, rt

Reference

Borylation using group IV metallocene under mild conditions

Marciasini, Ludovic D.; Vaultier, Michel; Pucheault, Mathieu, Tetrahedron Letters, 2014, 55(10), 1702-1705

Production Method 17

73183-34-3

37181-39-8

45788-92-9

936618-92-7

Reaction Conditions

1.1 Reagents: Pyridine Solvents: Acetone ,  Water ;  12 h, rt

Reference

Redox-Neutral Borylation of Aryl Sulfonium Salts via C-S Activation Enabled by Light

Huang, Chen; Feng, Jie ; Ma, Rui; Fang, Shuaishuai; Lu, Tao; et al, Organic Letters, 2019, 21(23), 9688-9692

Production Method 18

1073-06-9

73183-34-3

936618-92-7

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: Chloro[rel-(3aR,9aS)-1,3,3a,4,9,9a-hexahydro-1,3-bis(1-methylethyl)-4,9[1′,2′]-b… Solvents: tert-Butyl methyl ether ;  25 °C; 4 h, 25 °C
1.2 Reagents: Ammonium chloride Solvents: Water ;  0 °C

Reference

A Bicyclic N-Heterocyclic Carbene as a Bulky but Accessible Ligand: Application to the Copper-Catalyzed Borylations of Aryl Halides

Ando, Shin; Matsunaga, Hirofumi; Ishizuka, Tadao, Journal of Organic Chemistry, 2015, 80(19), 9671-9681

Production Method 19

73183-34-3

372-20-3

936618-92-7

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; Xu, Biping; Su, Weiping, ACS Catalysis, 2022, 12(15), 8904-8910

Production Method 20

73183-34-3

936618-92-7

Reaction Conditions

1.1 Catalysts: Tetramethylammonium fluoride ,  Bis[1,3-dihydro-1,3-bis(2,4,6-trimethylphenyl)-2H-imidazol-2-ylidene]nickel Solvents: Methylcyclopentane ;  15 h, 80 °C

Reference

Preparing (Multi)Fluoroarenes as Building Blocks for Synthesis: Nickel-Catalyzed Borylation of Polyfluoroarenes via C-F Bond Cleavage

Zhou, Jing; Kuntze-Fechner, Maximilian W.; Bertermann, Rudiger; Paul, Ursula S. D.; Berthel, Johannes H. J.; et al, Journal of the American Chemical Society, 2016, 138(16), 5250-5253

Production Method 21

935447-39-5

73183-34-3

936618-92-7

Reaction Conditions

1.1 Reagents: Silver phosphate Catalysts: Palladium chloride ,  X-Phos Solvents: Acetonitrile ;  17 h, 80 °C

Reference

Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron

Qiu, Di; Li, Songyi; Yue, Guanglu; Mao, Jinshan; Xu, Bei; et al, Tetrahedron Letters, 2021, 85,

3-Fluorophenylboronic acid pinacol ester Raw materials

• 1-Fluoro-3-iodobenzene
• 2,3-Dimethylbutane-2,3-diol
• sodium 3-fluorobenzenesulfinate
• 1,3,2-Dioxaborolan-2-amine, N,N,4,4,5,5-hexamethyl-
• Borate(1-),tetrafluoro-
• 1-Bromo-3-fluorobenzene
• Bis(pinacolato)diborane
• 3-Fluorophenol
• (3-Fluorophenyl)dimethylsulfonium
• Benzenediazonium, 3-fluoro-

3-Fluorophenylboronic acid pinacol ester Preparation Products

• 3-Fluorophenylboronic acid pinacol ester (936618-92-7)
• 2-(3,5-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (863868-36-4)

• 1. Excimer and exciplex formation in a pair of bright phosphorescent isomers constructed from Cu3(pyrazolate)3 and Cu3I3 coordination luminophores?
  Shun-Ze Zhan,Mian Li,Xiao-Ping Zhou,Dan Li,Seik Weng Ng RSC Adv., 2011,1, 1457-1459
• 2. Excellent peroxidase mimicking property of CuO/Pt nanocomposites and their application as an ascorbic acid sensor?
  Xinhuan Wang,Shuangfei Cai,Cui Qi Analyst, 2017,142, 2500-2506
• 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. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788
• 5. Etching of glass microchips with supercritical water?
  Pavel Karásek,Jakub Grym,Michal Roth,Josef Planeta,Franti?ek Foret Lab Chip, 2015,15, 311-318

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Halobenzenes Fluorobenzenes
• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

• 1308669-74-0(2-(6-Fluoronaphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 863868-37-5(2,6-Difluorophenylboronic acid, pinacol ester)
• 627526-35-6(1,3,2-Dioxaborolane, 2-(4-fluoro-1-naphthalenyl)-4,4,5,5-tetramethyl-)
• 876062-39-4(2-(2-Fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 303006-90-8(2-[2,5-difluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 819058-34-9(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline)
• 288101-48-4(2,4-Difluorophenylboronic acid, pinacol ester)
• 214360-58-4(4-Fluorophenylboronic acid, pinacol ester)
• 827614-70-0(4,4,5,5-Tetramethyl-2-(3,4,5-trifluorophenyl)-1,3,2-dioxaborolane)
• 863868-36-4(2-(3,5-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)