204862-91-9

Basic information

• Product Name: racemic BINAP
• CAS NO: 204862-91-9
• Molecular Weight: 638.685
• Mol File: 204862-91-9.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: racemic BINAP(CAS DataBase Reference)
• NIST Chemistry Reference: racemic BINAP(204862-91-9)
• EPA Substance Registry System: racemic BINAP(204862-91-9)

Safety Data

• Hazardous Substances Data: 204862-91-9(Hazardous Substances Data)

Upstream product

• 4559-70-0 Diphenylphosphine oxide 
• 187742-81-0 (R)-2-diphenylphosphino-2'-(trifluoromethanesulfonyloxy)-1,1'-binaphthyl 
• 499992-61-9 bis((R)-2-(diphenylphosphino)-2'-(diphenylphosphinyl)-1,1'-binaphthyl)dichloropalladium(II) 
• 76144-87-1 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl 
• 130164-89-5 2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene 
• 141807-44-5 (+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl 
• 132532-04-8 (R)-2-diphenylphosphinyl-2'-trifluoromethanesulfonyloxy-1,1'-binaphthalene 

Downstream Products

• 499992-64-2 phenyl((S)-2-(diphenylphosphino)-2'-(diphenylphosphinyl)-1,1'-binaphthyl-kappa⁽²⁾P,O)fluoropalladium(II) 
• 268545-63-7 (RRu)-[(p-cymene)RuCl(η2-(S)-BINPO-P,O)]SbF6 
• 267899-87-6 [(p-cymene)RuCl(η(2)-(S)-BINAP monoxide-P,O)]Cl 
• 268545-63-7 [(p-cymene)RuCl(η(2)-(R)-BINPO-P,O)]SbF6 
• 268545-59-1 [(p-cymene)RuCl(η(2)-(R)-BINAP monoxide-P,O)]Cl 
• 500116-40-5 bis((S)-2-(diphenylphosphino)-2'-(diphenylphosphinyl)-1,1'-binaphthyl)palladium⁽⁰⁾ 
• 213177-76-5 [PtCl₂((C₁₀H₆P(O)(C₆H₅)2)(C₁₀H₆P(C₆H₅)2))] 
• 499992-61-9 bis((R)-2-(diphenylphosphino)-2'-(diphenylphosphinyl)-1,1'-binaphthyl)dichloropalladium(II) 
• 500116-40-5 bis((R)-2-(diphenylphosphino)-2'-(diphenylphosphinyl)-1,1'-binaphthyl)palladium⁽⁰⁾ 
• 329362-53-0 [(η6-Cy)OsCl(η2-(S)-BINPO)]SbF6 
• 76144-87-1 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl 

Relevant articles and documents

Asymmetric C-C bond-formation reaction with Pd: How to favor heterogeneous or homogeneous catalysis?

The enantioselective allylic alkylation of (E)-1,3-diphenylallyl acetate was studied to clarify the heterogeneous or homogeneous character of the Pd/Al2O3-(R)-BINAP catalyst system. A combined approach was applied: the catalytic test

Palladium(II) and palladium(0) complexes of BINAP(O) (2-(diphenylphosphino)-2′-(diphenylphosphinyl)-1,1′-binaphthyl)

The coordination organopalladium chemistry of 2-(diphenylphosphino)-2′-(diphenylphosphinyl)-1,1′-binaphthyl (BINAP(O)) was found to be totally different from that of other phosphine-phosphine oxide ligands, as well as of BINAP. The reaction of [(MeCN)2PdCl2] with BINAP(O) (1 equiv) afforded [(BINAP(O))PdCl2] (1), in which BINAP(O) is P,O-chelated to Pd in the solid state (X-ray) and in solution (NMR). Treatment of 1 with free BINAP(O) led to the reversible formation of a P,P-bonded nonchelate, [(BINAP(O))2PdCl2] (2), which could not be isolated due to the equilibrium being strongly shifted toward 1. Reduction of 1 with LiBH4 in the presence of BINAP(O) afforded a new zerovalent Pd complex [(BINAP(O))2Pd] (3), in which both BINAP(O) ligands are P-bonded to Pd and one provides η2-arene coordination via the C=C bond adjacent to the phosphinyl group (X-ray). Oxidative addition of PhI to 3 led cleanly to [(BINAP(O))Pd(Ph)I] (4; Ph trans to O; X-ray) which was also prepared by the reaction of [Pd2(dba)3] with BINAPO and PhI. The ultrasound-promoted I/F exchange reaction of [(BINAPO)Pd(Ph)I] with AgF afforded [(BINAP(O))Pd(Ph)F] (5), which was decomposed thermally to produce a mixture of P-F and C-P reductive elimination products.

Method for making an optically active diphosphine ligand

The present invention provides a method for making compound (1) by reacting compound (2) with phosphine oxide (3) in the presence of a transition metal/phosphine complex and optionally reducing the reaction product: STR1 where n represents 0 or 1; the double line having a continuous line and a dotted line represents a double bond or a single bond such that the ring having the double line forms a naphthalene ring or an octahydronaphthalene ring with an adjacent benzene ring; Tf represents a trifluoromethanesulfonyl group; and Ar represents a phenyl group, a substituted phenyl group or a naphthyl group. The present invention provides an economical way to produce compound (1) as a ligand of a complex useful as a catalyst for a variety of asymmetric synthesis reactions.