130004-33-0

Basic information

• Product Name: (R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENECHLORO(P-CYMENE)RUTHENIUM CHLORIDE
• Synonyms: [(S)-2,2'-BIS-(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]-CHLORO-(P-CYMENE)-RUTHENIUMCHLORIDE;(S)-(-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENECHLORO(P-CYMENE)RUTHENIUM CHLORIDE;S-(-)-BINAP-CHLORO(P-CYMENE)RUTHENIUM CHLORIDE;(S)-(-)-2,2''-BIS(DIPHENYLPHOSPHINO)-1,1''-BINAPHTHYL]CHLORO(P-CYMENE)RUTHENIUM;[bis(diphenylphosphino)binaphthyl]chloro(p-cumene)RuCl;(S)-RuCl[(p-cymene(BINAP)Cl;(S)-(-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENECHLORO(P-CYMENE)RUTHENIUM CHLO;(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalenechloro(p-cymene)ruthenium chloride, ca 5% MeOH of cryst.
• CAS NO: 130004-33-0
• Molecular Formula: C₅₄H₄₆ClP₂Ru*Cl
• Molecular Weight: 928.87
• Product Categories: Ru
• Mol File: 130004-33-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: >100°C
• Boiling Point: 724.3 °C at 760 mmHg
• Flash Point: 419 °C
• Appearance: orange/Powder
• Storage Temp.: Freezer (-20°C)
• Solubility: Chloroform (Sparingly)
• Sensitive: Air Sensitive
• CAS DataBase Reference: (R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENECHLORO(P-CYMENE)RUTHENIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENECHLORO(P-CYMENE)RUTHENIUM CHLORIDE(130004-33-0)
• EPA Substance Registry System: (R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENECHLORO(P-CYMENE)RUTHENIUM CHLORIDE(130004-33-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 130004-33-0(Hazardous Substances Data)

Usage

Reaction

This catalyst has shown to effect the highly enantioselective hydrogenation of functionalized ketones where the substituents are dialkylamino, hydoxy, siloxy, carbonyl, ester, amide or thioester.

Chemical Properties

Brown crystalline powder

Uses

Takasago Ligands and Complexes for Asymmetric Reactions

Upstream product

• 52462-29-0 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 
• 76144-87-1 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl 
• 76144-87-1 (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) 

Relevant articles and documents

The Total Synthesis of Epothilone D as a Yardstick for Probing New Methodologies

Here, a concise and highly convergent synthesis of epothilone D was investigated, relying on fragments of equal complexity that could be prepared in gram scale quantities. The strategy to construct the fragments includes the use of a previously reported enantiospecific zinc-catalyzed cross-coupling of an α-hydroxy ester triflate with a Grignard reagent, the application of a hydroboration/boron–magnesium exchange sequence for the rapid construction of the Z-substituted trisubstituted double bond present in the natural product, and a Noyori-type hydrogenation to install the β-hydroxy ester moiety of the southern part. The key to success is the diastereoselective head-to-tail macrolactonization by an intramolecular addition of the corresponding ω-alkynyl-substituted carboxylic acids to construct a new stereocenter in the macrocyclic core structure in one single step.

On the mechanism of an asymmetric α,β-unsaturated carboxylic acid hydrogenation: Application to the synthesis of a PGD2 receptor antagonist

Ruthenium complexes employing axially chiral ligands were found to be effective asymmetric hydrogenation catalysts for the reduction of α,β-unsaturated ene acid 1-E to give 2, a prostaglandin D2 (PGD2) receptor antagonist. With [(S-B

Synthesis of New Cationic BINAP-Ruthenium(II) Complexes and their Use in Asymmetric Hydrogenation

Reaction of 2 (1) and (S)-BINAP gives cationic BINAP-ruthenium complexes of the formula Y (2) (X = Cl, Br, and I; Y = Cl, Br, I, BF4, and BPh4; arene = C6H6 and p-MeC6H4CHMe2) which are efficient catalyst precursors for enantioselective hydrogenation of various prochiral alkenic and ketonic substrates ; a crystal structure of (2) (with X = Cl, Y = BF4) was obtained.