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699616 Sigma-Aldrich

Chloro[tris(2,4-di-tert-butylphenyl)phosphite]gold

Synonym: [Tris(2,4-di-tert-butylphenyl)phosphite]gold chloride

  • CAS Number 915299-24-0

  • Empirical Formula (Hill Notation) C42H63AuClO3P

  • Molecular Weight 879.34

  •  MDL number MFCD11045473

  •  PubChem Substance ID 329762147

  •  NACRES NA.22

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Properties

Related Categories Catalysis and Inorganic Chemistry, Chemical Synthesis, Gold Catalysts, Gold Complexes
Quality Level   100
reaction suitability   core: gold
  reagent type: catalyst
mp   200-202 °C
SMILES string   Cl[Au].CC(C)(C)c1ccc(OP(Oc2ccc(cc2C(C)(C)C)C(C)(C)C)Oc3ccc(cc3C(C)(C)C)C(C)(C)C)c(c1)C(C)(C)C
InChI   1S/C42H63O3P.Au.ClH/c1-37(2,3)28-19-22-34(31(25-28)40(10,11)12)43-46(44-35-23-20-29(38(4,5)6)26-32(35)41(13,14)15)45-36-24-21-30(39(7,8)9)27-33(36)42(16,17)18;;/h19-27H,1-18H3;;1H/q;+1;/p-1
InChI key   GCWCLHMEYZKZRO-UHFFFAOYSA-M

Description

Application

Gold Catalysts — 21st Century ′Gold Rush′

• Intermolecular addition of carbon nucleophiles to 1,5 and 1,6 enynes

Catalyst for:
• [4C+2C] cycloadditions
• Cis-selective single-cleavagte skeletal cycloisomerization
• Diastereoselective Au-catalyzed intermolecular cyclopropanation
• Elucidating the mechanism of "endocyclic" skeletal rearrangement of 1,6-enynes
• Addition reactions

Packaging

500 mg in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Intramolecular Cycloaddition of 1,3-Enynes with Alkenes | Aldrich ChemFiles 2009, 9.5, 5.

In 2008, Echavarren and co-workers in their quest for finding more active gold catalysts for new reactions, reported the synthesis of pycnantuquinones A derivatives, catalyzed by [4+2] cycloaddition ...
William Sommer
Aldrich ChemFiles 2009, 9.5, 5.
Keywords: Catalysis, Chemfiles, Cycloadditions, Isomerizations, Ligands, Substitutions

Related Content

Gold Catalyst in Chemical Synthesis

Introduction Hashmi, Toste, Echavarren, and Haruta, among others, have fueled the advance of gold into the forefront of transition metal catalysis.1,2 Phosphine ligated gold(I) complexes have risen a...
Keywords: Asymmetric synthesis, Building blocks, Catalysis, Claisen rearrangement, Conia-Ene Reaction, Cyclizations, Cycloadditions, Cycloisomerizations, Cyclopropanations, Deprotonations, Ene reaction, Hydroaminations, Hydrogenations, Isomerizations, Ligands, Rautenstrauch rearrangements, Rearrangements, Reductions, Schmidt Reaction, Substitutions

Peer-Reviewed Papers
15

References

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