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Chemical Structure| 351019-18-6 Chemical Structure| 351019-18-6
Chemical Structure| 351019-18-6

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Synonyms: 6-Fluoropyridine-3-boronic acid

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Product Details of 2-Fluoropyridine-5-boronic acid

CAS No. :351019-18-6
Formula : C5H5BFNO2
M.W : 140.91
SMILES Code : C1=C(C=CC(=N1)F)B(O)O
Synonyms :
6-Fluoropyridine-3-boronic acid
MDL No. :MFCD03411559
InChI Key :OJBYZWHAPXIJID-UHFFFAOYSA-N
Pubchem ID :2783397

Safety of 2-Fluoropyridine-5-boronic acid

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

Application In Synthesis of 2-Fluoropyridine-5-boronic acid

* 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 [ 351019-18-6 ]

[ 351019-18-6 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 5467-57-2 ]
  • [ 351019-18-6 ]
  • [ 1165800-27-0 ]
YieldReaction ConditionsOperation in experiment
94% With potassium carbonate;[1,3-bis(2,6-diisopropylphenyl)imidazolidene](3-chloropiridyl)palladium(II) dichloride; In 1,4-dioxane; water; at 100℃; i) 2-(6-Fluoropyridin-3-yl)quinoline-4-carboxylic acid6-Fluoropyridine-3-boronic acid (1.6 g, 12 mmol), a IM aq. solution OfK2CO3 (25 mL) and PEPPSI (0.18 g, 0.26 mmol) were added sequentially to a solution of 2-chloro- quinoline-4-carboxylic acid (2.0 g, 9.6 mmol) in dioxane (25 mL). The reaction mixture was degassed and then heated at 1000C under a nitrogen atmosphere for 2h and then cooled to rt. The dioxane was removed by concentration in vacuo and the remaining residue was diluted with MeOH and citric acid to give a mixture of pH ~ 4. The layers were separated <n="244"/>and the aqueous phase was extracted with EtOAc. The combined organic layers were dried followed by concentration in vacuo to give the title compound (2.8 g, 94percent). 1H NMR (400 MHz, DMSO-J6) delta 9.10 (s, IH), 8.87-8.78 (m, IH), 8.60 (d, IH), 8.49 (s, IH), 8.15 (d, IH), 7.84 (t, IH), 7.74-7.67 (m, IH), 7.39-7.32 (m, IH); m/z (M+H)+ 269.1.
  • 2
  • [ 868656-97-7 ]
  • [ 351019-18-6 ]
  • [ 1093631-88-9 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 15h;Inert atmosphere; Reflux; 13c) Methyl 6-(6-fluoro-3-pyridinyl)-lH-indole-3-carboxylateMethyl 6-bromo-lH-indole-3-carboxylate (0.63 g, 2.48 mmol), 2- fluoropyridyl-5-boronic acid (0.435 g, 3.09 mmol), tetrakistriphenylphosphine palladium (0) (0.14 g, 0.012 mmol), 2 M sodium carbonate (5 mL, 10 mmol), and 1,2- dimethoxyethane (20 mL) were combined and heated at reflux with stirring under a nitrogen atmosphere for 15 hours. The reaction mixture was allowed to cool at room temperature and partitioned between water and ethyl acetate. The organic phase was separated, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give the crude product as a yellow solid. The crude product was purified by flash chromatography over silica gel with a dichloromethane methanol gradient (100:0 to 97:3) to give 0.606 g of methyl 6-(6-fluoro-3-pyridinyl)-lH-indole-3-carboxylate as a yellow solid. 1H NMR indicates that a minor impurity is present. The compound was used without further purification. 1H NMR (J6-DMSO, 400 MHz): delta 12.09 (br s, IH), 8.54 (d, J = 2 Hz, IH), 8.28 (dt, J = 8, 3 Hz, IH), 8.13 (d, J = 3 Hz, IH), 8.06 (d, J = 8 Hz, IH), 7.73 (s, IH), 7.51 (dd, J = 8, 2 Hz, IH), 7.27 (dd, J = 9, 3 Hz, IH), 3.80 (s, 3H). ES-LCMS m/z 269 (M - H)".
  • 3
  • [ 13067-94-2 ]
  • [ 351019-18-6 ]
  • [ 1374109-14-4 ]
YieldReaction ConditionsOperation in experiment
87% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; for 3.0h;Inert atmosphere; Reflux; Synthesis of 135 To a mixture of 79 (627 mg, 3.0 mmol), 99 (465 mg, 3.3 mmol) and 1,2-dimethoxyethane (20 ml), an aqueous 2M sodium carbonate solution (3 ml, 6.0 mmol) and tetrakistriphenylphosphine palladium (173 mg, 0.15 mmol) were added under an argon atmosphere, and the mixture was heated at reflux for 3 hours. The reaction solution was allowed to return to room temperature, diluted with ethyl acetate and then washed in turn with water and saturated saline. The organic layer was dried and the solvent was distilled off under reduced pressure, and then the residue was purified by silica gel flash column chromatography (eluting solvent: n-hexane/ethyl acetate = 4/1, 3/1) to obtain 135 (700 mg, 87%) as a pale yellow solid. mp 159-161C APCI-MS m/z 270[M+H]+
  • 4
  • [ 207399-07-3 ]
  • [ 351019-18-6 ]
  • C41H47FN3(1+) [ No CAS ]
  • 5
  • [ 7499-66-3 ]
  • [ 351019-18-6 ]
  • 6-(6-fluoropyridin-3-yl)naphthalen-2-amine [ No CAS ]
  • 6
  • [ 7499-66-3 ]
  • [ 351019-18-6 ]
  • tert-butyl [6-(6-fluoropyridin-3-yl)naphthalen-2-yl]carbamate [ No CAS ]
  • 7
  • [ 53848-17-2 ]
  • [ 351019-18-6 ]
  • C12H11FN2 [ No CAS ]
 

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