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665185 Sigma-Aldrich

Bis(chlorogold(I)) bis(diphenylphosphino)methane


Synonym: Methylenebis[diphenyl]phosphine gold complex

  • CAS Number 37095-27-5

  • Empirical Formula (Hill Notation) C25H22Au2Cl2P2

  • Molecular Weight 849.23

  •  MDL number MFCD08705280

  •  PubChem Substance ID 24884721

  •  NACRES NA.22



Related Categories Catalysis and Inorganic Chemistry, Chemical Synthesis, Gold Catalysts, Gold Complexes
Quality Level   100
assay   97%
reaction suitability   core: gold
  reagent type: catalyst
SMILES string   Cl[Au][PH](C[PH]([Au]Cl)(c1ccccc1)c2ccccc2)(c3ccccc3)c4ccccc4
InChI   1S/C25H22P2.2Au.2ClH/c1-5-13-22(14-6-1)26(23-15-7-2-8-16-23)21-27(24-17-9-3-10-18-24)25-19-11-4-12-20-25;;;;/h1-20H,21H2;;;2*1H/q;2*+1;;/p-2



Gold Catalysts — 21st Century ′Gold Rush′

Used for
• Pharmacological studies involving the anticancer activity of gold(I)-phosphine complexes as autophagy-inducing agents
• Triplet luminescent light emitting diodes with low turn-on voltage

Catalyst for:
• Stereoselective preparation of vinyltetrahydrofuran via intramolecular hydroalkoxylation
• Hydroamination and hydroalkoxylation reactions
• Asymmetric transition metal catalysis
• Gold(I) catalyzed intramolecular Schmidt reactions of homopropargyl azides


1 g in glass bottle

250 mg in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
NONH for all modes of transport
WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable


Certificate of Analysis (COA)

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Protocols & Articles


Acetylenic Schmidt Reaction

Pyrroles are important synthons in the synthesis of natural products. Toste and co-workers utilized the affinity and electron-donating property to synthesize pyrroles via the acetylenic Schmidt react...
William Sommer
Aldrich ChemFiles 2009, 9.5, 3.
Keywords: Chemfiles, Schmidt Reaction, Substitutions

DuPhos and BPE Phospholane Ligands

Asymmetric hydrogenation reactions represent the ideal process for the commercial manufacture of single-enantiomer compounds, because of the ease by which these robust procedures can be scaled up and...
Aldrich ChemFiles 2006, 6.8, 3.
Keywords: Addition reactions, Alkylations, Allylborations, Amidations, Aminations, Asymmetric catalysis, Asymmetric synthesis, Building blocks, Catalysis, Chemfiles, Crotylborations, Cycloadditions, Electronics, Hydrogenations, Ligands, Purification, Reductions, Reductive aminations, transformation

Gold Catalysis - Aldrich ChemFiles 2007, 7.5, 10.

Gold catalysis is playing an increasing role in organic synthesis for the facile construction of complex architectures not readily accessed by standard methods. Gold catalysts mediate unique C–C, C–O...
Aldrich ChemFiles 2007, 7.5, 10.
Keywords: Catalysis, Chemfiles, Enyne rearrangements, Heterocycle formation, Isomerizations, Methods, Organic synthesis, Rearrangements

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

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