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677264 Sigma-Aldrich

APhos

95%

Synonym: (4-(N,N-Dimethylamino)phenyl)di-tert-butyl phosphine, A-taPhos, [4-(Dimethylamino)phenyl]bis(tert-butyl)phosphine

  • CAS Number 932710-63-9

  • Empirical Formula (Hill Notation) C16H28NP

  • Molecular Weight 265.37

  •  MDL number MFCD09265102

  •  PubChem Substance ID 24885360

  •  NACRES NA.22

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Properties

Related Categories Buchwald Ligands and Complexes, Buchwald and Related Ligands, Catalysis and Inorganic Chemistry, Chemical Synthesis, Cross-Coupling,
assay   95%
mp   57-61 °C
functional group   phosphine
reaction suitability   reaction type: Buchwald-Hartwig Cross Coupling Reaction
  reaction type: Heck Reaction
  reaction type: Hiyama Coupling
  reaction type: Negishi Coupling
  reaction type: Sonogashira Coupling
  reaction type: Stille Coupling
  reaction type: Suzuki-Miyaura Coupling
  reagent type: ligand
reaction type: Cross Couplings
SMILES string   CN(C)c1ccc(cc1)P(C(C)(C)C)C(C)(C)C
InChI   1S/C16H28NP/c1-15(2,3)18(16(4,5)6)14-11-9-13(10-12-14)17(7)8/h9-12H,1-8H3
InChI key   IQTHEAQKKVAXGV-UHFFFAOYSA-N

Description

Application

Ligand used to prepare a palladium dichloride catalyst (678740) on treatment with PdCl2(COD). The catalyst effectively cross-couples aryl boronic acids with heteroaryl chlorides.

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS05  GHS05
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Advantages of A-Phos Palladium Complexes for Efficient Suzuki Coupling

The Suzuki-Miyaura cross-coupling reaction of heteroaryl halides is of particular interest to the pharmaceutical industry since many biologically active compounds are accessed through this methodolog...
Keywords: Catalysis, Coupling reactions, Cross couplings, Pharmaceutical, Solvents, Suzuki coupling

Aldrich ChemFiles 2007, 7.10, 6.| Non-Proprietary Phosphine Ligands

In the pharmaceutical industry, Pd-catalyzed processes have frequently been relied on for carrying out key bond formations. While there are many ligands that efficiently mediate C–C and C–N bond form...
William Sommer
Aldrich ChemFiles 2007, 7.10, 6.
Keywords: Aminations, Catalysis, Coupling reactions, Cross couplings, Eliminations, Ligands, Pharmaceutical

Related Content

A-Phos Palladium Complexes for Efficient Suzuki Coupling

Introduction The Suzuki-Miyaura cross-coupling reaction of heteroaryl halides is of particular interest to the pharmaceutical industry since many biologically active compounds are accessed through th...
Keywords: Applications, Catalysis, Coupling reactions, Cross couplings, Pharmaceutical, Solvents, Suzuki coupling

Peer-Reviewed Papers
15

References

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