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Chemical Structure| 564483-19-8 Chemical Structure| 564483-19-8
Chemical Structure| 564483-19-8

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Chen, Zhi-Hao ; Daugulis, Olafs ; Brookhart, Maurice ;

Abstract: A well-defined Pd complex [(tBuXPhos)Pd(Me)(BArf)] bearing a bulky monophosphine ligand was synthesized and fully characterized. X-ray diffraction anal. shows that the 1,3,5-triisopropylaryl group of the dialkylbiaryl phosphine ligand exhibits a weak η6-interaction with the Pd(II) center. This catalyst exhibits excellent functional group tolerance and polymerizes propargyl esters containing benzoyl and acetyl groups, propargyl Me ether, propargyl alc., benzyl acetylene, and Ph acetylene to yield polymers with Mn values at 5-15 kDa with monomodal mol. weight distributions between ∼1.4 and 2.1.

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Product Details of t-BuXPhos

CAS No. :564483-19-8
Formula : C29H45P
M.W : 424.64
SMILES Code : CC(C1=C(C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C(C)C)=CC(C(C)C)=C1)C
MDL No. :MFCD06411306
InChI Key :SACNIGZYDTUHKB-UHFFFAOYSA-N
Pubchem ID :11618717

Safety of t-BuXPhos

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

Application In Synthesis of t-BuXPhos

* 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 [ 564483-19-8 ]

[ 564483-19-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 890315-75-0 ]
  • [ 367-27-1 ]
  • [ 131274-22-1 ]
  • [ 564483-19-8 ]
  • [ 890316-65-1 ]
YieldReaction ConditionsOperation in experiment
With citric acid;tris-(dibenzylideneacetone)dipalladium(0); palladium diacetate; In ethyl acetate; toluene; Example 557 0.018 mL of 2,4-difluorophenol was added to 1 mL of toluene suspension containing 10 mg of 60percent sodium hydride at room temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 15 minutes. After the reaction mixture was cooled to room temperature, 0.5 mL of toluene solution containing 4.7 mg of 2-(di-tert-butylphosphino)-2',4',6'-triisopropylbiphenyl, 1.7 mg of palladium acetate and 70 mg of tert-butyl 2-(benzamido)-4-bromobenzoate was added and the resulting mixture was heated to reflux under nitrogen atmosphere for 4 hours. After the reaction mixture was cooled to room temperature, 4.5 mg of 60percent sodium hydride, 4.7 mg of 2-(di-tert-butylphosphino)-2',4',6'-triisopropylbiphenyl and 1.7 mg of palladium acetate were added and the resulting mixture was heated to reflux under nitrogen atmosphere for 2 hours. After the reaction mixture was cooled to room temperature, 0.018 mL of 2,4-difluorophenol, 7.4 mg of 60percent sodium hydride, 4.7 mg of 2-(di-tert-butylphosphino)-2',4',6'-triisopropylbiphenyl and 1.7 mg of palladium acetate were added and the resulting mixture was heated to reflux under nitrogen atmosphere for 2 hours. After the reaction mixture was cooled to room temperature, 1.6 mg of tri-tert-butylphosphine tetrafluoroborate and 5.1 mg of tris(dibenzylideneacetone)dipalladium(0) were added, and the resulting mixture was heated to reflux under nitrogen atmosphere for 1 hour and 30 minutes. 10percent citric acid aqueous solution and ethyl acetate were added after the reaction mixture was cooled to room temperature. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane: ethyl acetate = 4:1] to obtain tert-butyl 2-(benzamido)-4-(2,4-difluorophenoxy)benzoate.
  • 2
  • [ 100-02-7 ]
  • [ 890315-75-0 ]
  • [ 131274-22-1 ]
  • [ 564483-19-8 ]
  • [ 890315-31-8 ]
YieldReaction ConditionsOperation in experiment
With citric acid;tris-(dibenzylideneacetone)dipalladium(0); palladium diacetate; In ethyl acetate; toluene; Example 536 31 mg of 4-nitrophenol was added to 1.0 mL of toluene suspension containing of 8.9 mg of 60percent sodium hydride at room temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 15 minutes. After the reaction mixture was cooled to room temperature, 0.5 mL of toluene solution containing 3.8 mg of 2-(di-tert-butylphosphino)-2',4',6'-triisopropylbiphenyl, 1.3 mg of palladium acetate and 56 mg of tert-butyl 2-(benzamido)-4-bromobenzoate were added and the resulting mixture was heated to reflux under nitrogen atmosphere for 3 hours. After the reaction mixture was cooled to room temperature, 1.3 mg of tri-tert-butylphosphine tetrafluoroborate and 4.1 mg of tris(dibenzylideneacetone)dipalladium(0) were added and the resulting mixture was heated to reflux under nitrogen atmosphere for 4 hours. After the reaction mixture was cooled to room temperature, 10percent citric acid aqueous solution and ethyl acetate were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane: ethyl acetate = 10:1] to obtain 18 mg of tert-butyl 2-(benzamido)-4-(4-nitrophenoxy)benzoate as white solid. 1H-NMR (CDCl3) delta: 1.65 (9H, s), 6.79 (1H, dd, J = 8.8, 2.4 Hz), 7.12-7.17 (2H, m), 7.50-7.61 (3H, m), 8.01-8.06 (2H, m), 8.09 (1H, d, J = 8.8 Hz), 8.23-8.29 (2H, m), 8.74 (1H, d, J = 2.4 Hz), 12.36 (1H, s).
  • 3
  • [ 52522-40-4 ]
  • [ 564483-19-8 ]
  • [ 1354022-32-4 ]
  • [ 1354022-31-3 ]
 

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