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Chemical Structure| 481681-02-1 Chemical Structure| 481681-02-1
Chemical Structure| 481681-02-1

4-Fluoro-3-(hydroxymethyl)benzeneboronic acid

CAS No.: 481681-02-1

4.5 *For Research Use Only !

Cat. No.: A129856 Purity: 98%

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Product Details of [ 481681-02-1 ]

CAS No. :481681-02-1
Formula : C7H8BFO3
M.W : 169.95
SMILES Code : OCC1=CC(B(O)O)=CC=C1F
MDL No. :MFCD08235075
InChI Key :PWMOQHMTXJYUGE-UHFFFAOYSA-N
Pubchem ID :21865588

Safety of [ 481681-02-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of [ 481681-02-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 481681-02-1 ]

[ 481681-02-1 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 99725-13-0 ]
  • [ 481681-02-1 ]
YieldReaction ConditionsOperation in experiment
To a solution of 5-bromo-2-fluoro-benzylalcohol [(L.] Oeq. ) from Step 1 in THF (0. [1M)] at-78C was added dropwise n-BuLi (2.2eq.). The mixture was stirred at-78C for 15min then [TRI-ISOPROPYLBORONATE] (2.2eq.) was added. The final mixture was warm slowly to rt, stirred for lh and quenched with HCl [(1M).] After stirring for lh, the mixture was extracted with EtOAc (2x). The combined organic extracts were washed with water, brine, dried over [NA2SO4,] filtered and concentrated. Stirring in Hex: EtOAc: H20 (90: 9: 1) for 12h afforded the title compound which was isolated by filtration as a white solid.
  • 2
  • [ 481681-02-1 ]
  • [ 942189-39-1 ]
  • [ 1093064-47-1 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 80℃; A suspension of 3-bromo-5-nitro-1-trityl-1 H-indazole 1 (6 g, 12.41 mmol), 4- fluoro-3-hydroxymethylphenylboronic acid 10AV (2 g, 12.87 mmol), Pd(dppf)CI2 (800 mg, 0.98 mmol) and K3PO4 (6 g, 28.30 mmol) in 124 ml_ of dioxane/H2O (25:6) was heated to 80C for overnight. After removal of most of the solvent, the black residue was diluted with EtOAc (250 ml_) and H2O (60 ml_). The resulting mixture was filtered through a pad of Celite. Additional 150 ml_ of EtOAc was used to wash the Celite cake. The filtrates were combined. The aqueous layer was separated and the organic layer was washed with brine, dried (MgSO4) and concentrated to give crude 3-(4- fluoro-3-hydroxymethylphenyl)-5-nitro-1-trityl-1 H-indazole 11AV (8.2 g) as a greenish yellow solid.
  • 3
  • [ 3934-20-1 ]
  • [ 481681-02-1 ]
  • [ 1312603-21-6 ]
  • 4
  • [ 481681-02-1 ]
  • [ 1312603-28-3 ]
  • 5
  • [ 481681-02-1 ]
  • C28H31FN4O3 [ No CAS ]
  • C28H31FN4O3 [ No CAS ]
  • 6
  • [ 481681-02-1 ]
  • [ 1312603-66-9 ]
  • 7
  • [ 481681-02-1 ]
  • 5-bromo-2-(3-(methylsulfonyl)propoxy)-3-(trifluoromethyl)pyridine [ No CAS ]
  • (2-fluoro-5-(6-(3-(methylsulfonyl)propoxy)-5-(trifluoromethyl)pyridin-3-yl)phenyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate; In tetrahydrofuran; water; at 70℃; for 2.0h; Step C.(2-Fluoro-5-(6-(3-(methylsulfonyl)propoxy)-5-(trifluoromethyl)pyridin-3- yDphenvDmethanol The solution of 5-bromo-2-(3-(methylsulfonyl)propoxy)-3-(trifluoromethyl)pyridine (500 mg, 1.381 mmol), <strong>[481681-02-1][4-fluoro-3-(hydroxymethyl)phenyl]boronic acid</strong> (352 mg, 2.071 mmol), PdOAc2 (12.40 mg, 0.055 mmol), potassium carbonate (382 mg, 2.76 mmol) and 2- dicyclohexylphosphino-2',6'-dimethoxybiphenyl (34.0 mg, 0.083 mmol) in THF (4 ml)/Water (0.8 ml) was heated at 70 C for 2h. The reaction mixture was diluted with H2O, and extracted with EtOAc three times. The combined extracts were washed with brine, dried over MgS04, filtered, concentrated and purified by flash chromatography on silica gel (0-60%EtOAc/hexanes) to give the title compound. MS m/e (M+H+): 408.
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate; In tetrahydrofuran; water; at 70℃; for 2.0h; Step C.(2-Fluoro-5-(6-(3-(methylsulfonyl)propoxy)-5-(trifluoromethyl)pyridin-3- yDphenvDmethanol The solution of 5-bromo-2-(3-(methylsulfonyl)propoxy)-3-(trifluoromethyl)pyridine (500 mg, 1.381 mmol), <strong>[481681-02-1][4-fluoro-3-(hydroxymethyl)phenyl]boronic acid</strong> (352 mg, 2.071 mmol), PdOAc2 (12.40 mg, 0.055 mmol), potassium carbonate (382 mg, 2.76 mmol) and 2- dicyclohexylphosphino-2',6'-dimethoxybiphenyl (34.0 mg, 0.083 mmol) in THF (4 ml)/Water (0.8 ml) was heated at 70 C for 2h. The reaction mixture was diluted with H2O, and extracted with EtOAc three times. The combined extracts were washed with brine, dried over MgS04, filtered, concentrated and purified by flash chromatography on silica gel (0-60%EtOAc/hexanes) to give the title compound. MS m/e (M+H+): 408.
  • 8
  • [ 481681-02-1 ]
  • 7-bromo-N-(3-fluorophenyl)-2-oxo-1,2-dihydroquinoline-4-carboxamide [ No CAS ]
  • 7-(4-fluoro-3-(hydroxymethyl)phenyl)-N-(3-fluorophenyl)-2-oxo-1,2-dihydroquinoline-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 24.0h;Inert atmosphere; General procedure: To a suspension of compound 6i (0.76 mmol) in 3mL dioxane:water (4:1), the boronic acid reagent (0.76 mmol) and Cs2CO3(270 mg, 0.83 mmol) was added. The mixture was purged using nitrogen gas then PdCl2(dppf) (10 mg, 0.014 mmol) was added under inert condition. The mixture was heated to 100 C for 24 h under argon and then cooled to room temperature. Filtration using celite, then water (30 mL) was added and the resulting mixture was extracted with EtOAc. The organic phase was dried over MgSO4, filtered, and dried under vacuum. The crude product was purified by flash chromatography (dichloromethane:MeOH 9.8:0.2) to afford the compounds described below.
  • 9
  • [ 481681-02-1 ]
  • [ 1093064-49-3 ]
  • 10
  • [ 481681-02-1 ]
  • [ 1093064-48-2 ]
 

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