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Chemical Structure| 168267-41-2

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Product Details of 3,4-Difluorophenylboronic acid

CAS No. :168267-41-2
Formula : C6H5BF2O2
M.W : 157.91
SMILES Code : C1=C(C=CC(=C1F)F)B(O)O
MDL No. :MFCD00807405
InChI Key :RMGYQBHKEWWTOY-UHFFFAOYSA-N
Pubchem ID :2734337

Safety of 3,4-Difluorophenylboronic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of 3,4-Difluorophenylboronic 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 [ 168267-41-2 ]

[ 168267-41-2 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 621-38-5 ]
  • [ 168267-41-2 ]
  • <i>N</i>-(3',4'-difluoro-biphenyl-3-yl)-acetamide [ No CAS ]
  • 2
  • [ 79832-89-6 ]
  • [ 168267-41-2 ]
  • [ 134412-17-2 ]
  • 3
  • [ 479691-42-4 ]
  • [ 168267-41-2 ]
  • [ 1567327-00-7 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; at 95℃;Inert atmosphere; A mixture of tert-butyl 4-(2-chloropyrimidin-4-yl)piperazine-1-carboxylate (10.0g, 33.5mmol), (3,4-difluorophenyl)boronic acid (7.90g, 50.2mmol), 1M aq Na2CO3 (45 mL, 90.0 mmol), tetrakis(triphenylphosphine)palladium (0) (4.6 g, 4.02 mmol), and DME (300 mL) was stirred at 95 C overnight under N2 atmosphere. After cooling to room temperature, the mixture was stirred at room temperature for 15h, diluted with water, and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, and concentrated in vacuo to give 14 as a brown oil. This product was used for next reaction without further purification.
  • 4
  • [ 7343-33-1 ]
  • [ 168267-41-2 ]
  • 3-bromo-1-(3,4-difluorophenyl)-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With pyridine; copper diacetate; In dichloromethane; at 20℃; for 72h;Molecular sieve; Diacetoxycopper (18.4 g, 101.4 mmol), bromo-triazole (lOg, 67.6 mmol), and 4A molecular sieves (250 mg, 0.33 mmol) were mixed in DCM, to which 4-difluorophenyl)boronic acid (14.9g, 94.6 mmol), pyridine (10.9 mL, 135.2 mmol) was added. The mixture was stined at RT under air for 3 days. LCMS showed that no starting material remaining and desired product was formed. The reaction was filtered and the solid was washed with additional DCM (200 ml). The combined organic layer was concentrated with silica gel and dry-loaded to purify on silica gel (240 grams column, 10-90percent ethyl acetate:hexanes) to afford 10.5 g (60percent) of desired product JW3-c. ?H NMR (400 MHz, DMSO-D6) oe 9.30 (s, 1H), 8.08 - 7.96 (m, 1H), 7.77 - 7.62 (m, 2H) ppm. ESI-MS m/z calc. 25 8.95566, found 260.32 (M+1)+; Retention time: 0.96 minutes.
54% With pyridine; In dichloromethane; at 20℃; for 72h;Molecular sieve; Copper(II) acetate (approximately 18.42 g, 101.4 mmol), <strong>[7343-33-1]3-bromo-1H-1,2,4-triazole</strong> (10 g, 67.59 mmol), and 4 A molecular sieves (250 mg/0.33 mmol) were combined in dichloromethane and treated with 3,4-difluorophenyl boronic acid (14.94 g, 94.63 mmol), and pyridine (approximately 10.69 g, 10.93 mL, 135.2 mmol). The mixture was stirred at room temperature under air for 3 days. The reaction was filtered and the solid was washed with additional dichloromethane (200 mL). The combined organic layers were concentrated with silica gel and dry-loaded to purify on silica gel to afford 3-bromo-1-(3,4-difluorophenyl)-1,2,4-triazole (10.5 g, 54percent). MR (400 MHz, DMSO-^e) delta 9.30 (s, 1H), 8.08 - 7.96 (m, 1H), 7.77 - 7.62 (m, 2H) ppm. ESI-MS m/z calc. 258.95566, found 260.32 (M+l)+; Retention time: 0.96 minutes.
  • 5
  • [ 20358-03-6 ]
  • [ 168267-41-2 ]
  • 2-amino-5-(3,4-difluorophenyl)benzothiazole [ No CAS ]
  • 6
  • [ 39549-79-6 ]
  • [ 168267-41-2 ]
  • 2-(3,4-difluorophenyl)-7-methyl-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one [ No CAS ]
  • 7
  • [ 885588-14-7 ]
  • [ 168267-41-2 ]
  • methyl 2-(3,4-difluorophenyl)-5-fluoroisonicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; at 100℃; for 16.0h;Inert atmosphere; A mixture of compound <strong>[885588-14-7]methyl 2-bromo-5-fluoroisonicotinate</strong> (110 g, 470.04 mmol, 1.0 eq.), (3,4-difluorophenyl)boronic acid (111.34 g, 705.06 mmol, 1.5 eq), Pd(dppf)Cl2 (8.60 g, 11.75 mmol, 0.025 eq) and potassium carbonate (129.92 g, 940.08 mmol, 2.0 eq) in 1,4-dioxane (1. Pd(dppf)Cl21 L) was heated to 100C for 16 hours under N2. The mixture was diluted with H2O (500 mL) and EtOAc(1.3 L) and stirred for 15 mins. The organic layer was separated, washed with brine (500 mL), dried over Na2SO4 and concentrated, the residue purified by combi-flash (5%~50% EtOAcin PE) and trituration (PE:EA=50/1, 100 mL) to afford methyl 2-(3,4- difluorophenyl)-5-fluoroisonicotinate (Intermediate A).1H NMR (CDCl3400MHz): d 8.56 (d, J=2.0 Hz, 1H), 8.05 (d, J=5.6 Hz, 1H), 7.79 (ddd, J=2.4, 8.4, 10.8 Hz, 1H), 7.64 (td, J=2.8, 8.8 Hz, 1H), 7.26 - 7.11 (m, 1H), 3.94 (s, 3H).
 

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