Production Method 1

73183-34-3

86308-26-1

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Catalysts: Triphenylphosphine ,  Cuprous iodide Solvents: Dimethylformamide ;  18 h, 25 °C

Reference

Expedient copper-catalyzed borylation reactions using amino acids as ligands

Liu, Meng-Yan; et al, Chinese Chemical Letters, 2015, 26(3), 373-376

Production Method 2

25015-63-8

86308-26-1

Reaction Conditions

1.1 Catalysts: Sodium tert-butoxide ,  2564747-00-6 ;  24 h, 60 °C

Reference

Manganese-Catalyzed Hydroboration of Terminal Olefins and Metal-Dependent Selectivity in Internal Olefin Isomerization-Hydroboration

Garhwal, Subhash ; et al, Inorganic Chemistry, 2021, 60(1), 494-504

Production Method 3

25015-63-8

86308-26-1

Reaction Conditions

1.1 Catalysts: Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]dirhodium Solvents: Toluene

Reference

Rhodium- and ruthenium-catalyzed dehydrogenative borylation of vinylarenes with pinacolborane: stereoselective synthesis of vinylboronates

Murata, Miki; et al, Bulletin of the Chemical Society of Japan, 2002, 75(4), 825-829

Production Method 4

7642-09-3

25015-63-8

86308-26-1

Reaction Conditions

1.1 Catalysts: [2-(Diphenylphosphino-κP)benzenaminato-κN][(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2… Solvents: Benzene-d6 ;  40 °C

Reference

Addition of a B-H Bond across an Amido-Cobalt Bond: CoII-H-Catalyzed Hydroboration of Olefins

Pang, Maofu; et al, Organometallics, 2018, 37(9), 1462-1467

Production Method 5

7642-09-3

25015-63-8

86308-26-1

Reaction Conditions

1.1 Reagents: Sodium triethylborohydride Catalysts: Iron, [6-[[bis(1,1-dimethylethyl)phosphino-κP]methyl]-2,2′-bipyridine-κN1,κN1′]d… ,  (SP-5-54)-[2-[[Bis(1,1-dimethylethyl)phosphino-κP]oxy]-6-(6-methyl-2-pyridinyl-κ… Solvents: Toluene ;  2 h, 23 °C

Reference

Iridium complexes of new NCP pincer ligands: catalytic alkane dehydrogenation and alkene isomerization

Jia, Xiangqing; et al, Chemical Communications (Cambridge, 2014, 50(75), 11056-11059

Production Method 6

76-09-5

2344-23-2

86308-26-1

Reaction Conditions

Reference

Organoboranes. 32. Homologation of alkylboronic esters with methoxy(phenylthio)methyllithium: regio- and stereocontrolled aldehyde synthesis from olefins via hydroboration

Brown, Herbert C.; et al, Journal of the American Chemical Society, 1983, 105(20), 6285-9

Production Method 7

638-45-9

25015-63-8

86308-26-1

Reaction Conditions

1.1 Reagents: Lithium methoxide Catalysts: Titanocene dichloride Solvents: tert-Butyl methyl ether ;  30 min, 50 °C
1.2 24 h, 50 °C

Reference

Catalytic Boration of Alkyl Halides with Borane without Hydrodehalogenation Enabled by Titanium Catalyst

Wang, Xianjin ; et al, Angewandte Chemie, 2021, 60(22), 12298-12303

Production Method 8

73183-34-3

86308-26-1

Reaction Conditions

1.1 Reagents: Methanol ,  Potassium tert-butoxide Catalysts: Tricyclohexylphosphine ,  Cuprous chloride Solvents: Tetrahydrofuran ;  30 min, rt
1.2 1 h, 0 °C

Reference

Copper(I)-catalyzed carbon-halogen bond-selective boryl substitution of alkyl halides bearing terminal alkene moieties

Iwamoto, Hiroaki; et al, Chemical Communications (Cambridge, 2015, 51(47), 9655-9658

Production Method 9

25015-63-8

86308-26-1

Reaction Conditions

Reference

Reactions of Fluoroalkanes with Mg-Mg Bonds: Scope, sp3C-F/sp2C-F Coupling and Mechanism

Coates, Greg; et al, Chemistry - A European Journal, 2018, 24(61), 16282-16286

Production Method 10

25015-63-8

86308-26-1

Reaction Conditions

1.1 Reagents: Lithium methoxide Catalysts: Titanocene dichloride Solvents: tert-Butyl methyl ether ;  30 min, 60 °C
1.2 24 h, 60 °C

Reference

Catalytic Boration of Alkyl Halides with Borane without Hydrodehalogenation Enabled by Titanium Catalyst

Wang, Xianjin ; et al, Angewandte Chemie, 2021, 60(22), 12298-12303

Production Method 11

76-09-5

64770-04-3

86308-26-1

Reaction Conditions

Reference

Organoboranes. 30. Convenient procedures for the synthesis of alkyl- and alkenylboronic acids and esters

Brown, Herbert C.; et al, Organometallics, 1983, 2(10), 1311-16

Production Method 12

4050-45-7

7688-21-3

25015-63-8

86308-26-1

Reaction Conditions

1.1 Reagents: Sodium triethylborohydride Catalysts: Iron, [6-[[bis(1,1-dimethylethyl)phosphino-κP]methyl]-2,2′-bipyridine-κN1,κN1′]d… ,  (SP-5-54)-[2-[[Bis(1,1-dimethylethyl)phosphino-κP]oxy]-6-(6-methyl-2-pyridinyl-κ… Solvents: Toluene ;  0.5 h, 23 °C

Reference

Iridium complexes of new NCP pincer ligands: catalytic alkane dehydrogenation and alkene isomerization

Jia, Xiangqing; et al, Chemical Communications (Cambridge, 2014, 50(75), 11056-11059

Production Method 13

73183-34-3

86308-26-1

Reaction Conditions

1.1 Catalysts: Tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[(1,2,3,4,5,6-η)-1,3,5-trimethy… ,  2-[[Bis(1,1-dimethylethyl)silyl]methyl]-1,10-phenanthroline ;  20 h, 120 °C

Reference

Iridium-Catalyzed C(sp3)-H Borylation Using Silyl-Bipyridine Pincer Ligands

Kawazu, Ryohei; et al, Angewandte Chemie, 2022, 61(22),

Production Method 14

73183-34-3

86308-26-1

Reaction Conditions

1.1 Reagents: Lithium methoxide Catalysts: Triphenylphosphine ,  Cuprous iodide Solvents: Dimethylformamide ;  18 h, 25 °C

Reference

Alkylboronic Esters from Copper-Catalyzed Borylation of Primary and Secondary Alkyl Halides and Pseudohalides

Yang, Chu-Ting; et al, Angewandte Chemie, 2012, 51(2), 528-532

Production Method 15

73183-34-3

86308-26-1

Reaction Conditions

1.1 Reagents: Sodium methoxide Catalysts: Tris(dibenzylideneacetone)dipalladium ,  Phosphine, bis(1,1-dimethylethyl)methyl-, tetrafluoroborate(1-) (1:1) Solvents: 1,4-Dioxane ;  24 h, 25 °C

Reference

Alkylboronic Esters from Palladium- and Nickel-Catalyzed Borylation of Primary and Secondary Alkyl Bromides

Yi, Jun; et al, Advanced Synthesis & Catalysis, 2012, 354(9), 1685-1691

Production Method 16

76-09-5

16343-08-1

86308-26-1

Reaction Conditions

1.1 Reagents: Sulfuric acid magnesium salt (1:1) Solvents: Diethyl ether ;  24 h, 25 °C

Reference

Suzuki-Miyaura cross-couplings of secondary allylic boronic esters

Glasspoole, Ben W.; et al, Chemical Communications (Cambridge, 2012, 48(9), 1230-1232

Production Method 17

25015-63-8

86308-26-1

Reaction Conditions

1.1 Catalysts: 1943723-13-4 Solvents: Benzene-d6 ;  1 h, rt

Reference

Diverse Activation Modes in the Hydroboration of Aldehydes and Ketones with Germanium, Tin, and Lead Lewis Pairs

Schneider, Julia; et al, Angewandte Chemie, 2017, 56(1), 333-337

Production Method 18

7642-09-3

25015-63-8

86308-26-1

Reaction Conditions

1.1 Catalysts: Sodium tert-butoxide ,  2564747-02-8 Solvents: Tetrahydrofuran ;  24 h, 60 °C

Reference

Manganese-Catalyzed Hydroboration of Terminal Olefins and Metal-Dependent Selectivity in Internal Olefin Isomerization-Hydroboration

Garhwal, Subhash ; et al, Inorganic Chemistry, 2021, 60(1), 494-504

Production Method 19

13269-52-8

25015-63-8

86308-26-1

Reaction Conditions

1.1 Catalysts: Sodium tert-butoxide ,  2564747-02-8 Solvents: Tetrahydrofuran ;  24 h, 60 °C

Reference

Manganese-Catalyzed Hydroboration of Terminal Olefins and Metal-Dependent Selectivity in Internal Olefin Isomerization-Hydroboration

Garhwal, Subhash ; et al, Inorganic Chemistry, 2021, 60(1), 494-504

Production Method 20

13269-52-8

25015-63-8

86308-26-1

Reaction Conditions

1.1 Reagents: Sodium triethylborohydride Catalysts: Iron, [6-[[bis(1,1-dimethylethyl)phosphino-κP]methyl]-2,2′-bipyridine-κN1,κN1′]d… ,  (SP-5-54)-[2-[[Bis(1,1-dimethylethyl)phosphino-κP]oxy]-6-(6-methyl-2-pyridinyl-κ… Solvents: Toluene ;  2 h, 23 °C

Reference

Iridium complexes of new NCP pincer ligands: catalytic alkane dehydrogenation and alkene isomerization

Jia, Xiangqing; et al, Chemical Communications (Cambridge, 2014, 50(75), 11056-11059

Production Method 21

73183-34-3

86308-26-1

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Magnetite (Fe3O4) (complex with hydroxylated copper dichloride) ,  Cupric chloride (hydroxylated complex with magnetite) Solvents: Methanol ,  Toluene ;  96 h, 60 °C

Reference

Impregnated Copper on Magnetite as Recyclable Catalyst for the Addition of Alkoxy Diboron Reagents to C-C Double Bonds

Cano, Rafael; et al, Journal of Organic Chemistry, 2010, 75(10), 3458-3460

Production Method 22

154820-94-7

86308-26-1

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium ,  Poly(oxy-1,2-ethanediyl), α-[4-[[3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trime… Solvents: Water ;  24 h, 1 atm, 45 °C

Reference

Environmentally responsible, safe, and chemoselective catalytic hydrogenation of olefins: ppm level Pd catalysis in recyclable water at room temperature

Takale, Balaram S.; et al, Green Chemistry, 2020, 22(18), 6055-6061

Production Method 23

4050-45-7

25015-63-8

86308-26-1

Reaction Conditions

1.1 Catalysts: [2-(Diphenylphosphino-κP)benzenaminato-κN][(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2… Solvents: Benzene-d6 ;  40 °C

Reference

Addition of a B-H Bond across an Amido-Cobalt Bond: CoII-H-Catalyzed Hydroboration of Olefins

Pang, Maofu; et al, Organometallics, 2018, 37(9), 1462-1467

Production Method 24

3761-92-0

25015-63-8

86308-26-1

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  1 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 25

73183-34-3

86308-26-1

Reaction Conditions

Reference

Reactions of Fluoroalkanes with Mg-Mg Bonds: Scope, sp3C-F/sp2C-F Coupling and Mechanism

Coates, Greg; et al, Chemistry - A European Journal, 2018, 24(61), 16282-16286

Production Method 26

25015-63-8

86308-26-1

Reaction Conditions

1.1 Catalysts: Sodium tert-butoxide ,  2564747-02-8 Solvents: Tetrahydrofuran ;  24 h, 60 °C

Reference

Manganese-Catalyzed Hydroboration of Terminal Olefins and Metal-Dependent Selectivity in Internal Olefin Isomerization-Hydroboration

Garhwal, Subhash ; et al, Inorganic Chemistry, 2021, 60(1), 494-504

2-hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Raw materials

• 2,3-Dimethylbutane-2,3-diol
• (2E)-2-Hexene
• trans-3-hexene
• Hexylmagnesium Bromide, 0.8 M solution in THF
• Boron, dibromohexyl[1,1'-thiobis[methane]]-, (T-4)-
• cis-2-Hexene
• cis-3-Hexene
• 1,3,2-Dioxaborolane,2-(1-hexen-1-yl)-4,4,5,5-tetramethyl-
• 1-Iodohexane
• Bis(pinacolato)diborane
• Pinacolborane
• Hexylboronic Acid
• Boronic acid, hexyl-, dimethyl ester

2-hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Preparation Products

• 2-hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (86308-26-1)

• 1. Emerging investigator series: first-principles and thermodynamics comparison of compositionally-tuned delafossites: cation release from the (001) surface of complex metal oxides?
  Joseph W. Bennett,Diamond T. Jones,Blake G. Hudson,Joshua Melendez-Rivera,Robert J. Hamers,Sara E. Mason Environ. Sci.: Nano, 2020,7, 1642-1651
• 2. Evolution in surface coverage of CH3NH3PbI3?XClXvia heat assisted solvent vapour treatment and their effects on photovoltaic performance of devices
  Dhirendra K. Chaudhary,Pramendra Kumar,Lokendra Kumar RSC Adv., 2016,6, 94731-94738
• 3. Evolution of cellulose into flexible conductive green electronics: a smart strategy to fabricate sustainable electrodes for supercapacitors
  Tengfei Yu,Yuehan Wu,Wei Li,Bin Li RSC Adv., 2014,4, 34134-34143
• 4. Excellent humidity sensor based on ultrathin HKUST-1 nanosheets?
  Qiaoe Wang,Meiling Lian,Xiaowen Zhu,Xu Chen RSC Adv., 2021,11, 192-197
• 5. Establishing plasmon contribution to chemical reactions: alkoxyamines as a thermal probe?
  Olga Guselnikova,Gérard Audran,Jean-Patrick Joly,Andrii Trelin,Evgeny V. Tretyakov,Vaclav Svorcik,Oleksiy Lyutakov,Sylvain R. A. Marque Chem. Sci., 2021,12, 4154-4161

• 1073371-70-6(4,4,5,5-tetramethyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentyl]-1,3,2-dioxaborolane)
• 66217-56-9(1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-octyl-)
• 200432-90-2(Heptyl, 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-)
• 69190-62-1(n-Butylboronic acid, pinacol ester)
• 167692-95-7(2-Cyclohexylethylboronic acid pinacol ester)
• 177035-82-4(1-Dodecylboronic acid pinacol ester)
• 123706-53-6(2-(cyclohexylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 67562-21-4(4,4,5,5-tetramethyl-2-pentyl-1,3,2-dioxaborolane)
• 141091-38-5(2-Decyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 915398-94-6(1,3,2-DIOXABOROLANE, 2-(4,4-DIMETHYLPENTYL)-4,4,5,5-TETRAMETHYL-)