866641-66-9

Basic information

• Product Name: (Acetonitrile)[(2-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate
• Synonyms: (Acetonitrile)[(2-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate;(Acetonitrile)[(biphenyl-2-yl)di-tert-butylphosphine]gold(1+) hexafluoroantimonate;2-(Di-t-butylphosphino)biphenyl(acetonitrile)gold(I) hexafluoroantiMonate, 99%;JohnPhos Au(MeCN)SbF6;2-(Di-t-butylphosphino))-1,1'-biphenyl(acetonitrile)gold(I) hexafluoroantimonate, 99%
• CAS NO: 866641-66-9
• Molecular Formula: C₂₂H₃₀AuNP*F₆Sb
• Molecular Weight: 0
• Product Categories: Catalysis and Inorganic Chemistry;Chemical Synthesis;Gold Catalysis;Gold Catalysts;GoldCatalysis and Inorganic Chemistry;Au
• Mol File: 866641-66-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 198-203 °C (D)
• Appearance: white to off-white/Powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive: air sensitive, moisture sensitiv
• CAS DataBase Reference: (Acetonitrile)[(2-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate(CAS DataBase Reference)
• NIST Chemistry Reference: (Acetonitrile)[(2-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate(866641-66-9)
• EPA Substance Registry System: (Acetonitrile)[(2-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate(866641-66-9)

Safety Data

• Hazard Codes: Xn,N
• Statements: 20/22-51/53
• Safety Statements: 61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 866641-66-9(Hazardous Substances Data)

Usage

Reaction

Gold catalyst used in the regio-and stereoselective synthesis of functionalized benzo[b]oxepines. Gold catalyst used in the cyclization reactions of o-(buta-1,3-diyn-1-yl-)-substituted N-aryl ureas. Gold catalyst used in the cycloisomerization of 1,7-enyne esters to structurally diverse cis-tetrahydropyridin-4-yl?ketones. Catalyst used in the synthesis of coumarin-containing natural products. Catalyst used in the synthesis of benzo[4,5]imidazo[1,2-a]quinazolinones.

InChI:InChI=1S/C20H27P.C2H3N.Au.6FH.Sb/c1-19(2,3)21(20(4,5)6)18-15-11-10-14-17(18)16-12-8-7-9-13-16;1-2-3;;;;;;;;/h7-15H,1-6H3;1H3;;6*1H;/q;;+1;;;;;;;+5/p-6

Upstream product

• 883995-03-7 [Ph₃P-Au-(NCCH₃)]⁽¹⁺⁾*SbF₆^(1-) 
• 1426437-86-6 Au(4-picoline)(tBu)2P(C₆H₄C₆H₅) 

Downstream Products

• 1426438-53-0 C₅₂H₆₇Au₂OP₂⁽¹⁺⁾*F₆Sb^(1-) 
• 1426438-65-4 C₅₁H₆₂Au₂NOP₂⁽¹⁺⁾*F₆Sb^(1-) 
• 883995-03-7 [Ph₃P-Au-(NCCH₃)]⁽¹⁺⁾*SbF₆^(1-) 
• 1426437-86-6 Au(4-picoline)(tBu)2P(C₆H₄C₆H₅) 

Relevant articles and documents

Quantitative evaluation of the stability of gem -diaurated species in reactions with nucleophiles

The reactivity of diaurated species toward nucleophiles was investigated. The reaction yields vinyl gold species and is described as simple SN2 ligand exchange at gold. Using suitably strong nucleophiles, equilibrium constants were determined to measure the stability of various diaurated species. On the basis of these equilibrium constants the influence of ligand and the nature of vinyl cores on the stability were analyzed. These results have direct implication for gold catalysis: it was demonstrated that vinyl gold intermediates bind the catalytic LAu+ species generally stronger than an alkyne (the substrate) by a factor of 106-109. This demonstrates that the formation of diaurated species from vinyl gold intermediates is thermodynamically favored in a catalytic reaction.