Production Method 1

933585-18-3

825644-26-6

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Cyclohexane ;  -78 °C; 1 h, -78 °C
1.2 Reagents: Trimethyl borate ;  1 h, -78 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 3, -78 °C → 5 °C

Reference

Sustainable Passerini-tetrazole three component reaction (PT-3CR): selective synthesis of oxaborol-tetrazoles

Singh, Akansha; et al, Chemical Communications (Cambridge, 2021, 57(76), 9708-9711

Production Method 2

933585-18-3

825644-26-6

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Toluene ,  Hexane ;  1 h, -78 °C; 30 min, -78 °C; -78 °C → -20 °C
1.2 Reagents: Trimethyl borate Solvents: Toluene ;  -78 °C; 1 h, -78 °C; -78 °C → -20 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  -20 °C; -20 °C → rt

Reference

Simple chiral derivatization protocols for 1H NMR and 19F NMR spectroscopic analysis of the enantiopurity of chiral diols

Yeste, Sonia Lozano; et al, Journal of Organic Chemistry, 2009, 74(1), 427-430

Production Method 3

94569-84-3

825644-26-6

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Methanol ;  rt; 1 h, reflux; cooled
1.2 Reagents: Sodium methoxide Solvents: Methanol ;  pH 11
2.1 Reagents: Butyllithium Solvents: Diethyl ether ,  Tetrahydrofuran ,  Hexane ;  -70 °C; 1 h, -70 °C
2.2 Reagents: Triethyl borate ;  -70 °C
2.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 3, -70 °C → 5 °C

Reference

Fluoro-substituted 2-formylphenylboronic acids: Structures, properties and tautomeric equilibria

Kowalska, Kornelia; et al, Journal of Fluorine Chemistry, 2016, 187, 1-8

Production Method 4

825644-26-6

Reaction Conditions

1.1 Reagents: 2,6-Lutidine ,  Boron tribromide Solvents: 1,2-Dichloroethane ;  4 h, rt
2.1 Reagents: Triethylamine Solvents: 1,2-Dichloroethane ;  2 h, rt
3.1 Reagents: Potassium bifluoride Solvents: Methanol ;  rt
4.1 Reagents: Chlorotrimethylsilane ,  Water Solvents: Acetonitrile ;  1 h, rt

Reference

Stereodivergent Access to [6.7]-Fused N-Heterocycles Bearing 1,3-Nonadjacent Stereogenic Centers by Pd-Catalyzed [4 + 2] Annulations

Ma, Zhan-Cai; et al, Organic Letters, 2023, 25(10), 1661-1666

Production Method 5

943310-52-9

825644-26-6

Reaction Conditions

1.1 Reagents: Potassium bifluoride Solvents: Methanol ;  rt
2.1 Reagents: Chlorotrimethylsilane ,  Water Solvents: Acetonitrile ;  1 h, rt

Reference

Stereodivergent Access to [6.7]-Fused N-Heterocycles Bearing 1,3-Nonadjacent Stereogenic Centers by Pd-Catalyzed [4 + 2] Annulations

Ma, Zhan-Cai; et al, Organic Letters, 2023, 25(10), 1661-1666

Production Method 6

139911-29-8

825644-26-6

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide ,  Potassium persulfate ,  Poly(methylhydrosiloxane) Catalysts: Ferrous chloride Solvents: Acetonitrile ,  Water ;  4 h, 80 °C

Reference

Bio-inspired iron-catalyzed oxidation of alkylarenes enables late-stage oxidation of complex methylarenes to arylaldehydes

Hu, Penghui; et al, Nature Communications, 2019, 10(1), 1-9

Production Method 7

933585-18-3

825644-26-6

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Diethyl ether ,  Tetrahydrofuran ;  15 min, rt; rt → -78 °C; 1 h, -78 °C
1.2 Reagents: Trimethyl borate ;  -78 °C → rt; 15 min, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 3, rt

Reference

A Three-Component Derivatization Protocol for Determining the Enantiopurity of Sulfinamides by 1H and 19F NMR Spectroscopy

Groleau, Robin R. ; et al, Journal of Organic Chemistry, 2020, 85(2), 1208-1215

Production Method 8

825644-26-6

Reaction Conditions

1.1 Reagents: Chlorotrimethylsilane ,  Water Solvents: Acetonitrile ;  1 h, rt

Reference

Stereodivergent Access to [6.7]-Fused N-Heterocycles Bearing 1,3-Nonadjacent Stereogenic Centers by Pd-Catalyzed [4 + 2] Annulations

Ma, Zhan-Cai; et al, Organic Letters, 2023, 25(10), 1661-1666

Production Method 9

94569-84-3

825644-26-6

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Methanol ;  rt; 1 h, rt → reflux; reflux → rt
1.2 Reagents: Sodium methoxide Solvents: Methanol ;  pH 11, rt
2.1 Reagents: Butyllithium Solvents: Diethyl ether ,  Tetrahydrofuran ,  Hexane ;  -78 °C; 1 h, -78 °C
2.2 Reagents: Triethyl borate ;  -78 °C; 1 h, -78 °C; -78 °C → rt
2.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 3, rt

Reference

Polycyclic heteroaromatics via hydrazine-catalyzed ring-closing carbonyl-olefin metathesis

Cho, Eun Kee; et al, Chemical Science, 2022, 13(8), 2418-2422

Production Method 10

94569-84-3

825644-26-6

Reaction Conditions

1.1 Reagents: Montmorillonite ((Al1.33-1.67Mg0.33-0.67)(Ca0-1Na0-1)0.33Si4(OH)2O10.xH2O) Solvents: Dichloromethane ;  rt; 0.5 h, rt
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Cyclohexane ;  -78 °C; 1 h, -78 °C
2.2 Reagents: Trimethyl borate ;  1 h, -78 °C
2.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 3, -78 °C → 5 °C

Reference

Sustainable Passerini-tetrazole three component reaction (PT-3CR): selective synthesis of oxaborol-tetrazoles

Singh, Akansha; et al, Chemical Communications (Cambridge, 2021, 57(76), 9708-9711

Production Method 11

94569-84-3

825644-26-6

Reaction Conditions

1.1 Catalysts: Sulfuric acid Solvents: Methanol ;  1.5 h, reflux; reflux → rt
1.2 Reagents: Triethylamine ;  rt
2.1 Reagents: Butyllithium Solvents: Diethyl ether ,  Tetrahydrofuran ;  15 min, rt; rt → -78 °C; 1 h, -78 °C
2.2 Reagents: Trimethyl borate ;  -78 °C → rt; 15 min, rt
2.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 3, rt

Reference

A Three-Component Derivatization Protocol for Determining the Enantiopurity of Sulfinamides by 1H and 19F NMR Spectroscopy

Groleau, Robin R. ; et al, Journal of Organic Chemistry, 2020, 85(2), 1208-1215

Production Method 12

94569-84-3

73183-34-3

825644-26-6

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  8 h, 90 °C
2.1 Reagents: Sodium periodate Solvents: Tetrahydrofuran ,  Water ;  20 min, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  2 h, rt

Reference

Discovery of 3-aryl substituted benzoxaboroles as broad-spectrum inhibitors of serine- and metallo-β-lactamases

Yan, Yu-Hang; et al, Bioorganic & Medicinal Chemistry Letters, 2021, 41,

Production Method 13

76-09-5

825644-26-6

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: 1,2-Dichloroethane ;  2 h, rt
2.1 Reagents: Potassium bifluoride Solvents: Methanol ;  rt
3.1 Reagents: Chlorotrimethylsilane ,  Water Solvents: Acetonitrile ;  1 h, rt

Reference

Stereodivergent Access to [6.7]-Fused N-Heterocycles Bearing 1,3-Nonadjacent Stereogenic Centers by Pd-Catalyzed [4 + 2] Annulations

Ma, Zhan-Cai; et al, Organic Letters, 2023, 25(10), 1661-1666

Production Method 14

456-48-4

75-64-9

825644-26-6

Reaction Conditions

1.1 overnight, 100 °C
2.1 Reagents: 2,6-Lutidine ,  Boron tribromide Solvents: 1,2-Dichloroethane ;  4 h, rt
3.1 Reagents: Triethylamine Solvents: 1,2-Dichloroethane ;  2 h, rt
4.1 Reagents: Potassium bifluoride Solvents: Methanol ;  rt
5.1 Reagents: Chlorotrimethylsilane ,  Water Solvents: Acetonitrile ;  1 h, rt

Reference

Stereodivergent Access to [6.7]-Fused N-Heterocycles Bearing 1,3-Nonadjacent Stereogenic Centers by Pd-Catalyzed [4 + 2] Annulations

Ma, Zhan-Cai; et al, Organic Letters, 2023, 25(10), 1661-1666

Production Method 15

933585-18-3

825644-26-6

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Diethyl ether ,  Tetrahydrofuran ,  Hexane ;  -70 °C; 1 h, -70 °C
1.2 Reagents: Triethyl borate ;  -70 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 3, -70 °C → 5 °C

Reference

Fluoro-substituted 2-formylphenylboronic acids: Structures, properties and tautomeric equilibria

Kowalska, Kornelia; et al, Journal of Fluorine Chemistry, 2016, 187, 1-8

Production Method 16

943310-52-9

825644-26-6

Reaction Conditions

1.1 Reagents: Sodium periodate Solvents: Tetrahydrofuran ,  Water ;  20 min, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  2 h, rt

Reference

Discovery of 3-aryl substituted benzoxaboroles as broad-spectrum inhibitors of serine- and metallo-β-lactamases

Yan, Yu-Hang; et al, Bioorganic & Medicinal Chemistry Letters, 2021, 41,

Production Method 17

139911-29-8

825644-26-6

Reaction Conditions

1.1 Reagents: Hydrogen peroxide Catalysts: 1-Hexadecanaminium, N,N,N-trimethyl-, (PB-7-34-111′1′2)-oxodiperoxy(2-pyridineca… Solvents: Water ;  24 h, 50 °C

Reference

Controlled and Predictably Selective Oxidation of Activated and Unactivated C(sp3)-H Bonds Catalyzed by a Molybdenum-Based Metallomicellar Catalyst in Water

Thiruvengetam, Prabaharan; et al, Journal of Organic Chemistry, 2022, 87(6), 4061-4077

(4-Fluoro-2-formylphenyl)boronic acid Raw materials

• 3-Fluorobenzaldehyde
• 2,3-Dimethylbutane-2,3-diol
• (4-Fluoro-2-methylphenyl)boronic Acid
• 2-Bromo-5-fluorobenzaldehyde
• 5-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
• Bis(pinacolato)diborane
• 2-methylpropan-2-amine
• 2-BROMO-5-FLUOROBENZALDEHYDE DIMETHYL ACETAL

(4-Fluoro-2-formylphenyl)boronic acid Preparation Products

• (4-Fluoro-2-formylphenyl)boronic acid (825644-26-6)

• 1. Elusive 2-aminofuran Diels–Alder substrates for a straightforward synthesis of polysubstituted anilines?
  Ana G. Neo,Ana Bornadiego,Jesús Díaz,Stefano Marcaccini,Carlos F. Marcos Org. Biomol. Chem., 2013,11, 6546-6555
• 2. Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation
  Matthew J. Gaunt,Jinquan Yu,Jonathan B. Spencer Chem. Commun., 2001, 1844-1845
• 3. Excited-state proton-coupled electron transfer within ion pairs?
  Gerald J. Meyer,Leif Hammarstr?m Chem. Sci., 2020,11, 3460-3473
• 4. Excimer–monomer switch: a reaction-based approach for selective detection of fluoride?
  Qiao Song,Angela Bamesberger,Lingyun Yang,Haley Houtwed,Haishi Cao Analyst, 2014,139, 3588-3592
• 5. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
  Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341

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

• 40138-16-7((2-formylphenyl)boronic acid)
• 139911-29-8((4-Fluoro-2-methylphenyl)boronic Acid)
• 163517-62-2(2-methyl-5-fluorophenylboronic acid)
• 871126-15-7((3-Fluoro-2-formylphenyl)boronic acid)
• 871126-22-6((2-fluoro-4-formylphenyl)boronic acid)
• 874290-62-7(2-Carboxy-5-fluorophenylboronic acid)
• 40138-17-8(2-Formyl-5-methylphenylboronic acid)
• 1256355-30-2((5-fluoro-2-formylphenyl)boronic acid)
• 874290-63-8(2-Borono-5-fluorobenzoic acid)
• 1072946-10-1(4-Fluoro-2,5-dimethylphenylboronic Acid)