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Chemical Structure| 1308669-74-0 Chemical Structure| 1308669-74-0

Structure of 1308669-74-0

Chemical Structure| 1308669-74-0

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Product Details of [ 1308669-74-0 ]

CAS No. :1308669-74-0
Formula : C16H18BFO2
M.W : 272.12
SMILES Code : CC1(C)C(C)(C)OB(C2=CC=C3C=C(F)C=CC3=C2)O1
MDL No. :MFCD22207164

Safety of [ 1308669-74-0 ]

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

Application In Synthesis of [ 1308669-74-0 ]

* 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 [ 1308669-74-0 ]

[ 1308669-74-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 324-41-4 ]
  • [ 73183-34-3 ]
  • [ 1308669-74-0 ]
YieldReaction ConditionsOperation in experiment
54% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90℃; General procedure: Aryl halide (1 equiv), bis-pinacolato-diboron (1.5-3 equiv), Pd(dppf)Cl2 (0.05-0.1 equiv), and KOAc (3-6 eq.) were suspended in DMF (2-6 mL). The mixture was then heated at 90 C for 2-6 h, cooled to rt, diluted with H2O (10 mL) and extracted with EtOAc (3 × 5 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo. The residue was purified by chromatography using a stepped gradient of 0-10% EtOAc in heptane to yield the desired boronic ester.
  • 2
  • [ 61676-62-8 ]
  • [ 324-41-4 ]
  • [ 1308669-74-0 ]
YieldReaction ConditionsOperation in experiment
67% As follows: the formula (6) Compound 9 (1.0g, 4.44mmol) was added to a single neck flask, pumping Vacuum / nitrogen filling repeated five times, followed by the addition of anhydrous THF30mL, isopropanol / liquid nitrogen after freezing to 78 C In30min slowly added dropwise 2.5M nbutyllithium(1.86mL, 4.66mmol), 1h, add isopropanol Pinacol borate (1.13mL,5.55mmol). Reaction 2h, slowly raising the temperature to room temperature, the reaction 8h, After the reaction was added towater, the product was extracted with methylene chloride, the organic phase was dried over anhydrous magnesium sulfate,separated to The solvent, separated and purified by silica gel column chromatography to give a white solid (6) compound 10co 0.8g, yield 67%.
65% A solution of n-BuLi in n-hexane (2.5M, 1.86mL, 4.67mmol) was added dropwise to a solution of <strong>[324-41-4]2-bromo-6-fluoronaphthalene</strong> (1.00g, 4.44mmol) in anhydrous THF (20mL) under nitrogen at-78C. After the reaction was kept at-78C for 1h, isopropoxyboronic acid pinacol ester (1.12mL, 5.56mmol) was added. The mixture was left to warm up to room temperature overnight. Then it was evaporated under vacuum. The residue was treated with water and extracted with CH2Cl2. The organic phase was further washed with water and brine, and dried over MgSO4. Upon concentration under vacuum, the crude product was purified by column chromatography on silica gel using CH2Cl2 as the eluent to obtain a white solid (0.785g, 65%). 1H NMR (300MHz, DMSO): delta 8.25 (s, 1H), 8.09-8.14 (m, 1H), 7.88 (d, J=8.28Hz, 1H), 7.68-7.75 (m, 2H), 7.40-7.46 (m, 1H), 1.31 (s, 12H).
  • 3
  • [ 1000623-95-9 ]
  • [ 1308669-74-0 ]
  • [ 1469882-38-9 ]
YieldReaction ConditionsOperation in experiment
83% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 90℃;Inert atmosphere; General procedure: Pd(PPh3)4 (35mg, 0.03mmol) was added to a mixture of 3,6-bis(5-bromothiophen-2- yl)-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (0.35g, 0.51mmol) and 2-naphthyl boronic acid (0.22g, 1.29mmol) in toluene (25mL), ethanol (10mL) and aqueous Na2CO3 solution (2M, 5mL) under N2. After the reaction was heated overnight at 90C, the volatile was evaporated. The residue was treated with water and extracted with CH2Cl2. The organic layer was separated, dried over anhydrous MgSO4, filtered and then concentrated. The crude product was purified by column chromatography using petroleum ether/dichloromethane (v/v=3/1) as eluent to afford a deep mulberry solid in 89% yield (0.36g).
83% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; at 135℃; for 3h;Inert atmosphere; Under a nitrogen atmosphere the formula (5) compound 7 (150mg, 0. 22mmol) and the formula (6) Compound 10) (150mg, 0. 55mmol) and 5ml concentration is 2M Na2C03 solution was added to a solution of 5ml of ethanol and toluene 50ml reaction flask, followed by addition of a molar ratio of 5% Pd (PPh3) 4, was heated to 135 C reflux for 3 hours. Cooled to room temperature, extracted with methylene chloride to the aqueous phase as a colorless, organic phase was dried with MgS04, the organic solvent was removed under reduced pressure using a mixed solvent of petroleum ether and methylene chloride as the eluent over a silica gel column to give 150mg FIG on formula (5) compound 8, as shown in 83% yield.
 

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