246231-79-8

Basic information

• Product Name: (R)-1-[(S)-2-[BIS[4-(TRIFLUOROMETHYL)PHENYL]PHOSPHINO]FERROCENYL]-ETHYLDI-TERT-BUTYLPHOSPHINE
• Synonyms: JOSIPHOS SL-J011-1;JOSIPHOS SL-J011-2;(S,S)-1-[1-(DI-TERT-BUTYLPHOSPHINO)ETHYL]-2-[BIS[4-(TRIFLUOROMETHYL)PHENYL]PHOSPHINO]FERROCENE;(S)-1-[(R)-2-[BIS[4-(TRIFLUOROMETHYL)PHENYL]PHOSPHINO]FERROCENYL]-ETHYLDI-TERT-BUTYLPHOSPHINE;(R,R)-1-[1-(DI-TERT-BUTYLPHOSPHINO)ETHYL]-2-[BIS[4-(TRIFLUOROMETHYL)PHENYL]PHOSPHINO]FERROCENE;(R)-(-)-1-[(S)-2-(BIS(4-TRIFLUOROMETHYLPHENYL)PHOSPHINO)FERROCENYL]ETHYL-DI-T-BUTYLPHOSPHINE;(R)-1-[(S)-2-[BIS[4-(TRIFLUOROMETHYL)PHENYL]PHOSPHINO]FERROCENYL]-ETHYLDI-TERT-BUTYLPHOSPHINE;(R)-(-)-1-[(S)-(2-DI-TERT-BUTYLPHOSPHINO)FERROCENYL]ETHYLDI-(4-TRIFLUOROMETHYLPHENYL)PHOSPHINE
• CAS NO: 246231-79-8
• Molecular Formula: C34H38F6FeP2 10*
• Molecular Weight: 678.45
• Product Categories: metallocene;Chiral Phosphine;Ferrocene Series;Josiphos Series
• Mol File: 246231-79-8.mol
• Article Data: 0

Chemical Properties

• Appearance: orange/Powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: (R)-1-[(S)-2-[BIS[4-(TRIFLUOROMETHYL)PHENYL]PHOSPHINO]FERROCENYL]-ETHYLDI-TERT-BUTYLPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-[(S)-2-[BIS[4-(TRIFLUOROMETHYL)PHENYL]PHOSPHINO]FERROCENYL]-ETHYLDI-TERT-BUTYLPHOSPHINE(246231-79-8)
• EPA Substance Registry System: (R)-1-[(S)-2-[BIS[4-(TRIFLUOROMETHYL)PHENYL]PHOSPHINO]FERROCENYL]-ETHYLDI-TERT-BUTYLPHOSPHINE(246231-79-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 246231-79-8(Hazardous Substances Data)

Usage

Reaction

Ferrocenylphosphine ligands of the type cpFecp(PR2)(*CH(CH3)PR'2) are a class of asymmetric ligands developed at Solvias in Basel, Switzerland. Ligands of this type are currently used industrially in the stereoselective synthesis of commercial products. A unique feature of these bidentate ligands is the presence of a fixed phosphine moiety and a stereogenic, functionalized side chain, which can be easily modified to accommodate electronic and steric requirements. Based on a versatile synthetic procedure starting with optically active ferrocenes of the type cpFecp(PR2)(*CH(CH3)X) [X = OAc or NR2], a variety of donor atoms can be introduced into the side chain. These ferrocene based phosphine ligands have wide application in the stereoselective hydrogenation of substituted acetamidoacrylates, enol acetates, β-ketoesters and simple alkenes. Useful as a ligand in Pd-catalyzed C-N bond-forming reactions. Pd-catalyzed enantioselective alkylative desymmetrization of meso-succinic anhydrides. Asymmetric hydrogenation of ketones and phosphinylketimines. Michael addition of Grignard reagents to α,α-unsaturated esters and thioesters. Boration of α,α-unsaturated esters and nitriles. Reaction of aryl halides with ammonia. Cu-catalyzed reduction of activated C=C bonds with PMHS. Regio- and enantioselective hydroboration of vinyl arenes. Rh-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes. 1,2-Migrations in Pd-catalyzed Negishi couplings with JosiPhos ligands. Catalyst for the homodimerization of ketoketenes. Ligand for the Rh catalyzed synthesis of lactones. Ligand for the Cu-catalyzed synthesis of syn and anti γ-amino alcohols.

Chemical Properties

Orange powder

General Description

sold in collaboration with Solvias AG

InChI:InChI=1/C29H33F6P2.C5H5.Fe/c1-19(37(26(2,3)4)27(5,6)7)24-9-8-10-25(24)36(22-15-11-20(12-16-22)28(30,31)32)23-17-13-21(14-18-23)29(33,34)35;1-2-4-5-3-1;/h8-19H,1-7H3;1-5H;/t19-;;/m0../s1

Downstream Products

• 942628-05-9 (C₅H₅)Fe(C₅H₃(CH(CH₃)P(C(CH₃)3)2)P(C₆H₄CF₃)2)PdCl₂