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

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

Uses

Used in Pharmaceutical Industry:
(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENECHLORO(P-CYMENE)RUTHENIUM CHLORIDE is used as a chiral catalyst for asymmetric reactions in the synthesis of pharmaceutical compounds. Its ability to selectively produce enantiomerically pure products is essential for the development of effective and safe drugs.
Used in Chemical Synthesis:
(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENECHLORO(P-CYMENE)RUTHENIUM CHLORIDE is used as a catalyst in various chemical synthesis processes, particularly in the production of enantiomerically pure compounds. Its high selectivity and reactivity make it a valuable tool in the synthesis of complex organic molecules.
Used in Research and Development:
(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENECHLORO(P-CYMENE)RUTHENIUM CHLORIDE is used as a research tool in the development of new asymmetric reaction methodologies and the study of reaction mechanisms. Its unique properties allow chemists to gain insights into the factors that govern enantioselectivity and develop new strategies for asymmetric synthesis.

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.

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.

PROCESS FOR MAKING CGRP RECEPTOR ANTAGONIST

The invention encompasses a novel process for making 2-[(8R)-8-(3,5-Difluorophenyl)-10-oxo-6,9-diazaspiro[4.5]dec-9-yl]-N-[(2R)-2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl]acetamide, which is a CGRP receptor antagonist useful for the treatment of migraine, using an asymmetric phase-transfer catalysis route. The invention also encompasses an efficient and practical synthesis of the (R)-acid intermediate, and generates the benzylic stereocenter in an enantioselective manner.

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

Asymmetric hydrogenation process

The present invention provides an asymmetric hydrogenation process for the preparation of chiral cycloalkanoindole DP receptor antagonists in high enantiomeric excess.

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.