Production Method 1

79230-20-9

73183-34-3

94242-85-0

Reaction Conditions

1.1 2 - 3 s, rt

Reference

Palladium-Catalyzed Remote Diborylative Cyclization of Dienes with Diborons via Chain Walking

Kanno, Shota; Kakiuchi, Fumitoshi ; Kochi, Takuya, Journal of the American Chemical Society, 2021, 143(46), 19275-19281

Production Method 2

73183-34-3

94242-85-0

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Solvents: Methanol ,  Water ;  48 h, 50 °C

Reference

Transition-Metal-Free Borylation of Alkyl Iodides via a Radical Mechanism

Liu, Qianyi; Hong, Junting; Sun, Beiqi; Bai, Guangcan; Li, Feng; et al, Organic Letters, 2019, 21(17), 6597-6602

Production Method 3

73183-34-3

94242-85-0

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Solvents: Methanol ,  Water ;  48 h, 50 °C

Reference

Method for preparing alkyl borate through boron esterification of alkyl halide without transition metal catalysis

, China, , ,

Production Method 4

76-09-5

13061-96-6

94242-85-0

Reaction Conditions

1.1 Catalysts: Calcium hydride Solvents: Pentane

Reference

Calcium Hydride

Gawley, Robert E.; Davis, Arnold, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

Production Method 5

76-09-5

13061-96-6

94242-85-0

Reaction Conditions

Reference

The Influence of Boryl Substituents on the Formation and Reactivity of Adjacent and Vicinal Free Radical Centers

Walton, John C.; McCarroll, Andrew J.; Chen, Qiao; Carboni, Bertrand; Nziengui, Roger, Journal of the American Chemical Society, 2000, 122(23), 5455-5463

Production Method 6

76-09-5

13061-96-6

94242-85-0

Reaction Conditions

1.1 Reagents: Calcium hydride Solvents: Pentane

Reference

Addition compounds of alkali metal hydrides. 28. Preparation of potassium dialkoxymonoalkylborohydrides from cyclic boronic esters. A new class of reducing agents

Brown, Herbert C.; Park, Won Suh; Cha, Jin Soon; Cho, Byung Tae; Brown, Charles A., Journal of Organic Chemistry, 1986, 51(3), 337-42

Production Method 7

94242-85-0

Reaction Conditions

Reference

Method for preparation of 2-trifluoromethyl-4,5-dihydrooxepin derivatives

, Japan, , ,

Production Method 8

25015-63-8

94242-85-0

Reaction Conditions

1.1 Solvents: p-Xylene ,  Benzene-d6 ;  rt

Reference

Mechanistic Studies of Copper-Catalyzed Asymmetric Hydroboration of Alkenes

Xi, Yumeng; Hartwig, John F., Journal of the American Chemical Society, 2017, 139(36), 12758-12772

Production Method 9

76-09-5

13061-96-6

94242-85-0

Reaction Conditions

1.1 Reagents: Sulfuric acid magnesium salt (1:1) Solvents: Diethyl ether ;  48 h, 25 °C

Reference

Suzuki-Miyaura cross-couplings of secondary allylic boronic esters

Glasspoole, Ben W.; Ghozati, Kazem; Moir, Jonathon W.; Crudden, Cathleen M., Chemical Communications (Cambridge, 2012, 48(9), 1230-1232

Production Method 10

76-09-5

13061-96-6

94242-85-0

Reaction Conditions

1.1 Reagents: Sulfuric acid magnesium salt (1:1) Solvents: Diethyl ether ;  48 h, rt

Reference

Ring-Opening Lithiation-Borylation of 2-Trifluoromethyl Oxirane: A Route to Versatile Tertiary Trifluoromethyl Boronic Esters

Nandakumar, Meganathan; Rubial, Belen; Noble, Adam ; Myers, Eddie L. ; Aggarwal, Varinder K., Angewandte Chemie, 2020, 59(3), 1187-1191

Production Method 11

73183-34-3

94242-85-0

Reaction Conditions

1.1 Catalysts: 2922856-92-4 (silica supported) Solvents: Cyclooctane ;  16 h, 500 psi, 150 °C

Reference

Silica Supported Organometallic IrI Complexes Enable Efficient Catalytic Methane Borylation

Staples, Orion; Ferrandon, Magali S.; Laurent, Guillaume P.; Kanbur, Uddhav; Kropf, A. Jeremy; et al, Journal of the American Chemical Society, 2023, 145(14), 7992-8000

Production Method 12

73183-34-3

94242-85-0

Reaction Conditions

1.1 Reagents: Cyclohexane Catalysts: Diaquatetrakis[μ-[4′-[bis(4′-carboxy[1,1′-biphenyl]-4-yl)phosphino][1,1′-bipheny… (reaction products with di-μ-chlorobis(1,5-cyclooctadiene)diiridium) ;  15 h, 50 bar, 110 °C; cooled

Reference

Metal-Organic Framework Stabilizes a Low-Coordinate Iridium Complex for Catalytic Methane Borylation

Feng, Xuanyu ; Song, Yang; Li, Zhe; Kaufmann, Michael; Pi, Yunhong; et al, Journal of the American Chemical Society, 2019, 141(28), 11196-11203

Production Method 13

76-09-5

13061-96-6

94242-85-0

Reaction Conditions

1.1 Reagents: Calcium hydride Solvents: Pentane

Reference

Calcium hydride

Gawley, Robert E.; Davis, Arnold, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-2

Production Method 14

76-09-5

13061-96-6

94242-85-0

Reaction Conditions

Reference

Determination of methylboronic acid in teboroxime by capillary gas chromatography

Both, Douglas A.; Ribick, Michael; Jemal, Mohammed, Journal of Chromatography, 1991, 585(2), 348-52

Production Method 15

1195-66-0

94242-85-0

78782-17-9

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 16

73183-34-3

94242-85-0

78782-17-9

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

2,4,4,5,5-Pentamethyl-1,3,2-dioxaborolane Raw materials

• Methoxyboronic acid pinacol ester
• 2,3-Dimethylbutane-2,3-diol
• Methylboronic acid
• Borate(1-), tetrakis[3,5-bis(trifluoromethyl)phenyl]-
• Bis(pinacolato)diborane
• Pinacolborane

2,4,4,5,5-Pentamethyl-1,3,2-dioxaborolane Preparation Products

• 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. An intramolecular tryptophan-condensation approach for peptide stapling?
  Eunice Y.-L. Hui,Bhimsen Rout,Yaw Sing Tan,Kok-Ping Chan,Charles W. Johannes Org. Biomol. Chem., 2018,16, 389-392
• 2. An artificial CO-releasing metalloprotein built by histidine-selective metallation?
  Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?o Chem. Commun., 2015,51, 3993-3996
• 3. An atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta[b]indoles from aniline-tethered alkylidenecyclopropanes with alkynes?
  Bo Cao,Yin Wei Chem. Commun., 2018,54, 2870-2873
• 4. An assessment of strategies for the development of solid-state adsorbents for vehicular hydrogen storage
  Mark D. Allendorf,Alauddin Ahmed,Tom Autrey,Jeffrey Camp,Eun Seon Cho,Maciej Haranczyk,Abhi Karkamkar,Di-Jia Liu,Katie R. Meihaus,Iffat H. Nayyar,Roman Nazarov,Donald J. Siegel,Vitalie Stavila,Jeffrey J. Urban,Srimukh Prasad Veccham,Brandon C. Wood Energy Environ. Sci., 2018,11, 2784-2812
• 5. An artificial photosynthetic system for photoaccumulation of two electrons on a fused dipyridophenazine (dppz)–pyridoquinolinone ligand?
  Philipp Traber,Stephan Kupfer,Stefanie Gr?fe,Isabelle Baussanne,Martine Demeunynck,Jean-Marie Mouesca,Serge Gambarelli,Vincent Artero,Murielle Chavarot-Kerlidou Chem. Sci., 2018,9, 4152-4159

• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

• 75927-49-0(Vinylboronic Acid Pinacol Ester)
• 364634-18-4(1,2-Bis((pinacolato)boryl)ethane)
• 70557-99-2(2-Iodomethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 76347-13-2(4,4,5,5-tetramethyl-2-(propan-2-yl)-1,3,2-dioxaborolane)
• 78782-17-9(Bis[(pinacolato)boryl]methane)
• 347389-74-6(2-Ethynyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 67562-19-0(1-Propylboronic Acid Pinacol Ester)
• 166330-03-6(2-(Bromomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 82954-89-0(2-Ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 83622-42-8(2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)