Production Method 1

76-09-5

62260-98-4

83622-41-7

Reaction Conditions

1.1 Reagents: Sulfuric acid magnesium salt (1:1) Solvents: Dichloromethane ;  18 h, rt

Reference

Diastereoselective Borocyclopropanation of Allylic Ethers Using a Boromethylzinc Carbenoid

Benoit, Guillaume; et al, Journal of the American Chemical Society, 2017, 139(4), 1364-1367

Production Method 2

76-09-5

83622-41-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -100 °C; 30 min, -100 °C
1.2 Reagents: Trimethyl borate ;  30 min, -100 °C
1.3 Reagents: Water
1.4 Solvents: Benzene ;  4 h, reflux

Reference

Efficient Total Synthesis of Bongkrekic Acid and Apoptosis Inhibitory Activity of Its Analogues

Matsumoto, Kenji; et al, Chemistry - A European Journal, 2015, 21(32), 11590-11602

Production Method 3

83622-41-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  45 min, -100 °C; 40 min, -100 °C
1.2 40 min, -100 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  -100 °C; 1 h, rt
2.1 Reagents: Sulfuric acid magnesium salt (1:1) Solvents: Dichloromethane ;  18 h, rt

Reference

Diastereoselective Borocyclopropanation of Allylic Ethers Using a Boromethylzinc Carbenoid

Benoit, Guillaume; et al, Journal of the American Chemical Society, 2017, 139(4), 1364-1367

Production Method 4

83622-41-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  45 min, -100 °C; 40 min, -100 °C
1.2 Reagents: Trimethyl borate ;  40 min, -100 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  cooled; 1 h, rt
2.1 Reagents: Sulfuric acid magnesium salt (1:1) Solvents: Dichloromethane ;  16 h, rt

Reference

Borocyclopropanation of Styrenes Mediated by UV-light Under Continuous Flow Conditions

Sayes, Morgane; et al, Angewandte Chemie, 2018, 57(41), 13514-13518

Production Method 5

76-09-5

62260-98-4

83622-41-7

Reaction Conditions

1.1 Reagents: Sulfuric acid magnesium salt (1:1) Solvents: Dichloromethane ;  16 h, rt

Reference

Borocyclopropanation of Styrenes Mediated by UV-light Under Continuous Flow Conditions

Sayes, Morgane; et al, Angewandte Chemie, 2018, 57(41), 13514-13518

Production Method 6

76-09-5

62260-98-4

83622-41-7

Reaction Conditions

Reference

Preparation of halomethaneboronates

Wuts, Peter G. M.; et al, Journal of Organometallic Chemistry, 1982, 234(2), 137-41

Production Method 7

76-09-5

83622-41-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  40 min, -100 °C; 30 min, -100 °C
1.2 Reagents: Trimethyl borate ;  30 min, -100 °C
1.3 Reagents: Hydrochloric acid Solvents: Water
1.4 Solvents: Benzene ;  rt; 48 h, reflux

Reference

Catalytic Asymmetric Total Syntheses of Quinine and Quinidine

Raheem, Izzat T.; et al, Journal of the American Chemical Society, 2004, 126(3), 706-707

Production Method 8

76-09-5

83622-41-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  45 min, -100 °C; 30 min, -100 °C
1.2 Reagents: Trimethyl borate ;  30 min, -100 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  -100 °C → rt
1.4 Solvents: Toluene ;  72 h, reflux

Reference

Asymmetric Synthesis and Biological Screening of Quinoxaline-Containing Synthetic Lipoxin A4 Mimetics (QNX-sLXms)

de Gaetano, Monica; et al, Journal of Medicinal Chemistry, 2021, 64(13), 9193-9216

Production Method 9

83622-41-7

Reaction Conditions

1.1 -
2.1 Reagents: Sulfuric acid magnesium salt (1:1) Solvents: Chloroform ;  12 h, rt

Reference

Chiral Phosphoric Acid Dual-Function Catalysis: Asymmetric Allylation with α-Vinyl Allylboron Reagents

Gao, Shang; et al, Angewandte Chemie, 2020, 59(26), 10540-10548

Production Method 10

83622-41-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  45 min, -100 °C; 30 min, -100 °C
1.2 Reagents: Trimethyl borate ;  30 min, -100 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  1 h, rt
2.1 Solvents: Benzene ;  48 h, reflux

Reference

Discovery of LOU064 (Remibrutinib), a Potent and Highly Selective Covalent Inhibitor of Bruton's Tyrosine Kinase

Angst, Daniela ; et al, Journal of Medicinal Chemistry, 2020, 63(10), 5102-5118

Dichloromethyl pinacolboronate Raw materials

• 2,3-Dimethylbutane-2,3-diol
• (dichloromethyl)boronic acid

Dichloromethyl pinacolboronate Preparation Products

• Dichloromethyl pinacolboronate (83622-41-7)

• 1. An astrophysically-relevant mechanism for amino acid enantiomer enrichment
  Stephen P. Fletcher,Richard B. C. Jagt,Ben L. Feringa Chem. Commun., 2007, 2578-2580
• 2. Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers
  P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. Buda Phys. Chem. Chem. Phys., 2011,13, 10270-10279
• 3. An amide probe as a selective Al3+ and Fe3+ sensor inside the HeLa and a549 cell lines: Pictet–Spengler reaction for the rapid detection of tryptophan amino acid?
  Bidyut Kumar Kundu,Rinky Singh,Ritudhwaj Tiwari,Debasis Nayak New J. Chem., 2019,43, 4867-4877
• 4. An alumina stabilized graphene oxide wrapped SnO2 hollow sphere LIB anode with improved lithium storage?
  Xiang Liu,Qian Sun,A. B. Djuri?i?,Maohai Xie,Baohu Dai,Jinyao Tang,Charles Surya,Changzhong Liao,Kaimin Shih RSC Adv., 2015,5, 100783-100789
• 5. 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

• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Boronic acid derivatives Boronic acid esters

• 109737-45-3(1,3,2-Dioxaborolane, 2-(dichloromethyl)-4,5-bis(1-methylethyl)-,(4S,5S)-)
• 110744-85-9(4,6-Methano-1,3,2-benzodioxaborole, 2-(chloromethyl)hexahydro-3a,5,5-trimethyl-, (3aS,4S,6S,7aR)-)
• 3036778-81-8(dichlorobis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methane)
• 98632-84-9(1,3,2-Dioxaborolane, 2-(dichloromethyl)-4,5-dimethyl-, trans-)
• 89618-71-3(1,3,2-Dioxaborolane, 2-(dichloromethyl)-4,5-dimethyl-, (4R-trans)-)
• 83622-42-8(2-(Chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)