Production Method 1

73183-34-3

78782-17-9

94242-85-0

87100-15-0

25015-63-8

Reaction Conditions

1.1 Catalysts: Rhodium, [(1,2,3,4,5,6-η)-hexamethylbenzene][(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl… Solvents: Cyclohexane ;  14 h, 3500 kPa, 150 °C

Reference

Catalyst-controlled selectivity in the C-H borylation of methane and ethane

Cook, Amanda K.; Schimler, Sydonie D.; Matzger, Adam J.; Sanford, Melanie S., Science (Washington, 2016, 351(6280), 1421-1424

Production Method 2

74-95-3

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ;  24 h, 40 °C

Reference

Copper-Catalyzed/Promoted Cross-coupling of gem-Diborylalkanes with Nonactivated Primary Alkyl Halides: An Alternative Route to Alkylboronic Esters

Zhang, Zhen-Qi; Yang, Chu-Ting; Liang, Lu-Jun; Xiao, Bin; Lu, Xi; et al, Organic Letters, 2014, 16(24), 6342-6345

Production Method 3

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Chloro(1-methylethyl)magnesium Solvents: Tetrahydrofuran ;  20 min, -78 °C; 2.5 h, -78 °C
1.2 30 min, -78 °C; -78 °C → -55 °C; 24 h, -55 °C
1.3 Reagents: Ammonium chloride Solvents: Water ;  -55 °C; -55 °C → rt

Reference

Enantio- and Diastereoselective Synthesis of 1,2-Hydroxyboronates through Cu-Catalyzed Additions of Alkylboronates to Aldehydes

Joannou, Matthew V.; Moyer, Brandon S.; Meek, Simon J., Journal of the American Chemical Society, 2015, 137(19), 6176-6179

Production Method 4

74-95-3

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ;  24 h, 40 °C

Reference

Base-promoted, deborylative secondary alkylation of N-heteroaromatic N-oxides with internal gem-bis[(pinacolato)boryl]alkanes: a facile derivatization of 2,2'-bipyridyl analogues

Hwang, Chiwon; Jo, Woohyun; Cho, Seung Hwan, Chemical Communications (Cambridge, 2017, 53(54), 7573-7576

Production Method 5

1195-66-0

78782-17-9

94242-85-0

Reaction Conditions

1.1 Catalysts: 3,4,7,8-Tetramethyl-1,10-phenanthroline ,  Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]diiridium Solvents: Cyclohexene ;  16 h, 3447 kPa, 150 °C

Reference

Catalytic borylation of methane

Smith, Kyle T.; Berritt, Simon; Gonzalez-Moreiras, Mariano; Ahn, Seihwan; Smith, Milton R. III; et al, Science (Washington, 2016, 351(6280), 1424-1427

Production Method 6

70557-99-2

78782-17-9

364634-18-4

Reaction Conditions

1.1 Reagents: Sodium Solvents: Benzene

Reference

Addition Reactions of Bis(pinacolato)diborane(4) to Carbonyl Enones and Synthesis of (pinacolato)2BCH2B and (pinacolato)2BCH2CH2B by Insertion and Coupling

Ali, Hijazi Abu; Goldberg, Israel; Srebnik, Morris, Organometallics, 2001, 20(18), 3962-3965

Production Method 7

74-95-3

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Tetrabutylammonium iodide ,  Potassium methoxide Catalysts: Copper Solvents: Dimethylformamide ;  24 h, 80 °C

Reference

Facile synthesis of alkyl- and arylboronate esters enabled by a carbon nanotube supported copper catalyst

Saini, Suresh; Gavali, Deepak S.; Bhawar, Ramesh; Thapa, Ranjit; Dhayal, Rajendra S.; et al, Catalysis Science & Technology, 2023, 13(1), 147-156

Production Method 8

73183-34-3

78782-17-9

Reaction Conditions

1.1 Catalysts: Cupric chloride ,  1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene Solvents: Tetrahydrofuran ;  10 min, rt
1.2 Reagents: Potassium methoxide ;  10 min, rt
1.3 1 h, 60 °C

Reference

Highly efficient synthesis of alkylboronate esters via Cu(II)-catalyzed borylation of unactivated alkyl bromides and chlorides in air

Bose, Shubhankar Kumar; Brand, Simon; Omoregie, Helen Oluwatola; Haehnel, Martin; Maier, Jonathan; et al, ACS Catalysis, 2016, 6(12), 8332-8335

Production Method 9

74-95-3

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ;  24 h, 40 °C

Reference

Direct Light-Enabled Access to α-Boryl Radicals: Application in the Stereodivergent Synthesis of Allyl Boronic Esters

Marotta, Alessandro; Fang, Hao; Adams, Callum E.; Sun Marcus, Kailey; Daniliuc, Constantin G.; et al, Angewandte Chemie, 2023, 62(34),

Production Method 10

74-95-3

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ;  24 h, 40 °C

Reference

Direct light-enabled access to α-boryl radicals: application in the stereodivergent synthesis of allyl boronic esters

Marotta, Alessandro; Fang, Hao; Adams, Callum E.; Marcus, Kailey Sun; Daniliuc, Constantin G.; et al, ChemRxiv, 2023, 1, 1-9

Production Method 11

74-95-3

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Lithium methoxide Catalysts: Triphenylphosphine ,  Cuprous iodide Solvents: Dimethylformamide ;  24 h, rt

Reference

A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates

Sun, Chunrui; Potter, Bowman; Morken, James P., Journal of the American Chemical Society, 2014, 136(18), 6534-6537

Production Method 12

74-95-3

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ;  10 min, rt
1.2 12 h, rt

Reference

A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal

Liu, Xun; Deaton, T. Maxwell; Haeffner, Fredrik; Morken, James P., Angewandte Chemie, 2017, 56(38), 11485-11489

Production Method 13

74-95-3

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ;  10 min, rt
1.2 12 h, rt

Reference

Simple access to elusive α-boryl carbanions and their alkylation: an umpolung construction for organic synthesis

Hong, Kai; Liu, Xun; Morken, James P., Journal of the American Chemical Society, 2014, 136(30), 10581-10584

Production Method 14

73183-34-3

78782-17-9

Reaction Conditions

1.1 Catalysts: Cupric chloride ,  1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene Solvents: Tetrahydrofuran ;  10 min, rt
1.2 Reagents: Potassium methoxide ;  10 min, rt; 60 °C

Reference

A site-selective and stereospecific cascade Suzuki-Miyaura annulation of alkyl 1,2-bisboronic esters and 2,2'-dihalo 1,1'-biaryls

Willems, Suzanne; Toupalas, Georgios; Reisenbauer, Julia C.; Morandi, Bill, Chemical Communications (Cambridge, 2021, 57(32), 3909-3912

Production Method 15

74-95-3

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ;  rt; 24 h, rt

Reference

Enantiomerically Enriched Tris(boronates): Readily Accessible Conjunctive Reagents for Asymmetric Synthesis

Coombs, John R.; Zhang, Liang; Morken, James P., Journal of the American Chemical Society, 2014, 136(46), 16140-16143

Production Method 16

76-09-5

74-95-3

78782-17-9

Reaction Conditions

1.1 Reagents: 2,2′-Bi-1,3,2-benzodioxaborole Solvents: Dimethylformamide ;  6 h, 50 °C
1.2 Reagents: Triethylamine ;  1 h, rt

Reference

Electrooxidative Activation of B-B Bond in B2cat2: Access to gem-Diborylalkanes via Paired Electrolysis

Wang, Bingbing; Zhang, Xiangyu; Cao, Yangmin; Zou, Long; Qi, Xiaotian ; et al, Angewandte Chemie, 2023, 62(14),

Production Method 17

74-95-3

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ;  rt

Reference

Synthesis of a Biomimetic Tetracyclic Precursor of Aspochalasins and Formal Synthesis of Trichoderone A

Gayraud, Oscar; Laroche, Benjamin; Casaretto, Nicolas; Nay, Bastien, Organic Letters, 2021, 23(15), 5755-5760

Production Method 18

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Tetrabutylammonium iodide ,  Potassium tert-butoxide Catalysts: Dopamine (anchored on ferrite) ,  Copper (nano-Fe-DOPA supported) Solvents: Dimethylformamide ;  24 h, 80 °C

Reference

Efficient synthesis of alkylboronic esters via magnetically recoverable copper nanoparticle-catalyzed borylation of alkyl chlorides and bromides

Shegavi, Mahadev L.; Agarwal, Abhishek; Bose, Shubhankar Kumar, Green Chemistry, 2020, 22(9), 2799-2803

Production Method 19

74-95-3

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ;  24 h, 40 °C

Reference

Chemoselective Coupling of 1,1-Bis[(pinacolato)boryl]alkanes for the Transition-Metal-Free Borylation of Aryl and Vinyl Halides: A Combined Experimental and Theoretical Investigation

Lee, Yeosan; Baek, Seung-yeol; Park, Jinyoung; Kim, Seoung-Tae ; Tussupbayev, Samat ; et al, Journal of the American Chemical Society, 2017, 139(2), 976-984

Production Method 20

74-95-3

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ;  24 h, 40 °C
1.2 Solvents: Ethyl acetate

Reference

Organophotocatalytic N-O Bond Cleavage of Weinreb Amides: Mechanism-Guided Evolution of a PET to ConPET Platform

Soika, Julia; McLaughlin, Calum; Nevesely, Tomas; Daniliuc, Constantin G.; Molloy, John. J.; et al, ACS Catalysis, 2022, 12(16), 10047-10056

Production Method 21

74-95-3

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Lithium methoxide Catalysts: Cuprous iodide Solvents: Dimethylformamide ;  24 h, 40 °C
1.2 Reagents: Ethyl acetate

Reference

Organophotocatalytic N-O bond cleavage of Weinreb amides: mechanism-guided evolution of a PET to ConPET platform

Soika, Julia; McLaughlin, Calum; Nevesely, Tomas; Daniliuc, Constantin; Molloy, John. J.; et al, ChemRxiv, 2022, 1, 1-15

Production Method 22

73183-34-3

78782-17-9

Reaction Conditions

1.1 Reagents: Ethylmagnesium bromide Catalysts: N,N,N′,N′-Tetramethylethylenediamine ,  Manganese dibromide Solvents: 1,2-Dimethoxyethane ;  10 h
1.2 4 h, rt

Reference

Manganese-Catalyzed Borylation of Unactivated Alkyl Chlorides

Atack, Thomas C.; Cook, Silas P., Journal of the American Chemical Society, 2016, 138(19), 6139-6142

Bis[(pinacolato)boryl]methane Raw materials

• Methoxyboronic acid pinacol ester
• 2,3-Dimethylbutane-2,3-diol
• 2-Iodomethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Dibromomethane
• Bis(pinacolato)diborane

Bis[(pinacolato)boryl]methane Preparation Products

• 1,2-Bis((pinacolato)boryl)ethane (364634-18-4)
• Bis[(pinacolato)boryl]methane (78782-17-9)
• 2,4,4,5,5-Pentamethyl-1,3,2-dioxaborolane (94242-85-0)
• 2-Cyclohexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (87100-15-0)
• Pinacolborane (25015-63-8)

• 1. Exciting clusters, what does off-resonance actually mean??
  Goonay Yousefalizadeh,Shideh Ahmadi,Nicholas J. Mosey,Kevin G. Stamplecoskie Nanoscale, 2021,13, 242-252
• 2. Enabling stable MnO2 matrix for aqueous zinc-ion battery cathodes?
  Yiding Jiao,Liqun Kang,Jasper Berry-Gair,Kit McColl,Jianwei Li,Haobo Dong,Hao Jiang,Ryan Wang,Furio Corà,Dan J. L. Brett,Ivan P. Parkin J. Mater. Chem. A, 2020,8, 22075-22082
• 3. Examination of deposit in commercial diluted phosphoric acid
  Analyst, 1880,5, 146-147
• 4. Enantio- & chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330
  Sowmyalakshmi Venkataraman RSC Adv., 2015,5, 73807-73813
• 5. EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis?
  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739

• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Boronic acid derivatives Boronic acid esters
• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

• 339166-89-1(2,2'-Ethenylidenebis4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 94242-85-0(2,4,4,5,5-Pentamethyl-1,3,2-dioxaborolane)
• 2831416-43-2(2,2'-(iodomethylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane))
• 129422-12-4(iodozinc(1+),2-methanidyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 2413695-26-6(2-(2H3)methyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 1227056-25-8(1,3,2-Dioxaborolane, 2,2'-ethylidenebis[4,4,5,5-tetramethyl-)
• 1891091-47-6(4,4,5,5-tetramethyl-2-(methyl-13C)-1,3,2-dioxaborolane)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)