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Chemical Structure| 14243-64-2 Chemical Structure| 14243-64-2
Chemical Structure| 14243-64-2

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Synonyms: Chloro(triphenylphosphine)gold(I)

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Product Citations

Product Citations

Hintzsche, Samuel J. ; Vang, Zoua Pa ; Rivera Torres, Emanuel ; Podoski, Mykaela ; Clark, Joseph R. ;

Abstract: Selective deuterium installation into small molecules is becoming increasingly desirable not only for the elucidation of mechanistic pathways and studying biological processes but also because of deuterium's ability to favorably adjust the pharmacokinetic parameters of bioactive molecules. Fused bicyclic moieties, especially those containing heteroatoms, are prevalent in drug discovery and pharmaceuticals. Herein, we report a copper-catalyzed transfer hydrodeuteration of cyclic and heterocyclic alkenes, which enables the synthesis of chromans, quinolinones, and tetrahydronaphthalenes that are precisely deuterated at the benzylic position. We also demonstrate the ability to place one deuterium atom at the homobenzylic site of these scaffolds with high regioselectivity by swapping transfer reagents for their isotopic analogs. Furthermore, examples of chemoselective transfer hydrogenation and transfer deuteration are disclosed, allowing for the simultaneous incorporation of two vicinal hydrogen or deuterium atoms into a double bond.

Keywords: copper ; deuteration ; hydrodeuteration ; hydrogenation ; transition metal catalysis

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Product Details of Triphenylphosphinechlorogold

CAS No. :14243-64-2
Formula : C18H15AuClP
M.W : 494.71
SMILES Code : [Au]Cl.P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
Synonyms :
Chloro(triphenylphosphine)gold(I)
MDL No. :MFCD00009588
InChI Key :IFPWCRBNZXUWGC-UHFFFAOYSA-M
Pubchem ID :10874691

Safety of Triphenylphosphinechlorogold

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501

Application In Synthesis of Triphenylphosphinechlorogold

* 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 [ 14243-64-2 ]

[ 14243-64-2 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 103987-81-1 ]
  • [ 14243-64-2 ]
  • 8-quinolylethynyl(triphenylphosphine)gold [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With sodium ethanolate; In ethanol; at 20.0℃; for 17.0h; Under an argon atmosphere, Au(PPh3)Cl (0.20 g, 0.40 mmol), <strong>[103987-81-1]8-quinolylethyne</strong> (92 mg, 0.60 mmol) and ethanol (8 ml) were added to a Schlenk tube (25 mL) and sodium ethoxide (165 mul, 0.42 mmol; 2.55 M, ethanol solution) was added dropwise thereto, followed by stirring of the mixture at room temperature for 17 hours. After completion of the reaction, the resulting white precipitate was filtered and washed with ethanol (5 ml×three times), water (5 ml×four times) and ethanol (5 ml×three times) and dried under vacuum to give 0.23 g of the desired compound as a pale yellow powder (yield: 96%). 1H-NMR (400MHz, CDCl3) delta: 9.07 (dd, 1H), 8.12 (dd, 1H), 7.99 (dd, 1H), 7.68 (dd, 1H), 7.62-7.36 (m, 17H) 31P-NMR (160 MHz, CDCl3): 42.8 FAB-MS (M/Z) : 612 (M+H)+ Luminescence analysis: (CHCl3, 77K, Ex250nm) lambda (nm): 380, 526, 567 Elemental analysis: Found C: 57.06, H: 3.45, N: 2.33 Theoretical C: 56.97, H: 3.46, N: 2.29
  • 2
  • [ 14243-64-2 ]
  • [ 884494-34-2 ]
  • 5-fluoro-2-pyridylethynyl(triphenylphosphine)gold [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With sodium ethanolate; In ethanol; at 20℃; for 17h; Under an argon atmosphere, Au(PPh3)Cl (474 mg, 0.96 mmol), <strong>[884494-34-2]5-fluoro-2-pyridylethyne</strong> (174 mg, 1.44 mmol) and ethanol (19 ml) were added to a 20 ml Schlenk tube, and then sodium ethoxide (395 mul, 1.01 mmol: 2.55 mol/L (liter) in ethanol solution) was added dropwise thereto and the mixture was stirred at room temperature for 17 hours. After completion of the reaction, the resulting white precipitate was filtered and successively washed with ethanol (12 mlxthree times), water (12 mlxthree times) and ethanol (6 mlxthree times), followed by drying under vacuum to give 0.48 g of the desired compound as a yellow powder (yield: 86%). 1H-NMR (400 MHz, CDCl3) delta: 8.37 (d, 1H), 7.23-7.59 (m, 18H), (FAB-MS) (M/Z): 580 (M+H)+ Luminescence analysis: (CHCl3, 77K, Ex250nm) lambda (nm): 418, 446, 457 Elemental analysis: Found C: 51.51, H: 3.02, N: 2.47 Theoretical C: 51.83, H: 3.13, N: 2.42
  • 3
  • [ 14243-64-2 ]
  • [ 853909-08-7 ]
  • 6-fluoro-3-pyridylethynyl(triphenylphosphine)gold [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With sodium ethanolate; In ethanol; at 20℃; for 17h; Under an argon atmosphere, Au(PPh3)Cl (488 mg, 0.99 mmol), <strong>[853909-08-7]6-fluoro-3-pyridylethyne</strong> (179 mg, 1.48 mmol) and ethanol (20 ml) were added to a 20 ml Schlenk tube, and then sodium ethoxide (408 mul, 1.04 mmol: 2.55 mol/L (liter) in ethanol solution) was added dropwise thereto and the mixture was stirred at room temperature for 17 hours. After completion of the reaction, the resulting white precipitate was filtered and successively washed with ethanol (12 ml .x. three times), water (12 ml .x. three times) and ethanol (6 ml .x. three times), followed by drying under vacuum to give 0.42 g of the desired compound as a yellow powder (yield: 73percent). 1H-NMR (400 MHz, CDCl3) delta: 8.35 (s, 1H), 7.81-7.87 (m, 1H), 6.80-6.84 (m, 1H) (FAB-MS) (M/Z): 580 (M+H)+ Luminescence analysis: (CHCl3, 77K, Ex250nm) lambda (nm): 413, 433, 442, 452 Elemental analysis: Found C: 51.76, H: 3.05, N: 2.51 Theoretical C: 51.83, H: 3.13, N: 2.42
  • 4
  • [ 288-16-4 ]
  • [ 14243-64-2 ]
  • [ 167637-13-0 ]
  • 5
  • [ 14243-64-2 ]
  • [ 75-09-2 ]
  • [ 19362-77-7 ]
  • C48H38Au2P2S3*0.5CH2Cl2 [ No CAS ]
  • 6
  • [ 1554512-06-9 ]
  • [ 182482-25-3 ]
  • [ 14243-64-2 ]
  • [ 41860-46-2 ]
 

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