443347-10-2

Basic information

• Product Name: (R)-(+)-2,2',6,6'-TETRAMETHOXY-4,4'-BIS(DI(3,5-XYLYL)PHOSPHINO)-3,3'-BIPYRIDINE
• Synonyms: (S)-(-)-2,2',6,6'-Tetramethoxy-4,4'-bis(di(3,5-xylyl)phosphino)-3,3'-bipyridine,min.95%CTH-(S)-Xylyl-P-Phos;(r)-(+)-2,2',6,6'-tetramethoxy-4,4'-bis(di(3,5-xylyl)phosphino)-3,3'-bipyridine *cth-(r)-xylyl-p-phos*;(s)-(-)-2,2',6,6'-tetramethoxy-4,4'-bis(di(3,5-xylyl)phosphino)-3,3'-bipyridine *cth-(s)-xylyl-p-phos*;(R)-(+)-2,2'',6,6''-TETRAMETHOXY-4,4''-BIS(DI(3,5-XYLYL)PHOSPHINO)-3,3''-BIPYRIDINE *CTH-(R)-XYLYL-P-PHO;(S)-(-)-2,2',6,6'-Tetramethoxy-4,4'-bis(di(3,5-xylyl)phosphino)-3,3'-bipyridine, CTH-(S)-Xylyl-P-Phos, 95% Application:Asymmetric hydrogenation Store N2Ar;(S)-(-)-2,2',6,6'-Tetramethoxy-4,4'-bis(di(3,5-xylyl)phosphino)-3,3'-bipyridine *CTH-(S)-Xylyl-P-Pho;(3S)-4,4'-Bis[bis(3,5-dimethylphenyl)phosphino]-2,2',6,6'-tetramethoxy-3,3'-bipyridine;(S)-Xyl-P-Phos
• CAS NO: 443347-10-2
• Molecular Formula: C₄₆H₅₀N₂O₄P₂
• Molecular Weight: 756.85
• Mol File: 443347-10-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 158-162°C
• Appearance: white to pale yellow/Powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: Sparingly soluble in water.
• CAS DataBase Reference: (R)-(+)-2,2',6,6'-TETRAMETHOXY-4,4'-BIS(DI(3,5-XYLYL)PHOSPHINO)-3,3'-BIPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-2,2',6,6'-TETRAMETHOXY-4,4'-BIS(DI(3,5-XYLYL)PHOSPHINO)-3,3'-BIPYRIDINE(443347-10-2)
• EPA Substance Registry System: (R)-(+)-2,2',6,6'-TETRAMETHOXY-4,4'-BIS(DI(3,5-XYLYL)PHOSPHINO)-3,3'-BIPYRIDINE(443347-10-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 443347-10-2(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

(S)-(-)-2,2',6,6'-Tetramethoxy-4,4'-bis(di(3,5-xylyl)phosphino)-3,3'-bipyridine is used in Pharmaceutical and industry applications.

Reactions

Chiral ligand for the asymmetric hydrogenation of β-keto esters. Chiral ligand for enantioselective rhodium-catalyzed [2+2+2] carbocyclization reactions. Chiral ligand for ruthenium catalyzed hydrogenation of (E)-β-(acylamino)acrylates to β-amino acids. The Rhodium complex gives higher enantioselectivity for hydrogenation of (Z)-β-(acylamino)acrylates to β-amino acids. Chiral ligand for copper-catalyzed asymmetric hydrosilylation of ketones. Chiral ligand for asymmetric allylic substitution reactions using boronic acids as nucleophiles. Gives useful selectivity in asymmetric Pauson-Khand-type cyclizations.

Upstream product

• 442686-32-0 4-[bis-(3,5-dimethyl-phenyl)-phosphinoyl]-3-bromo-2,6-dimethoxy-pyridine 
• 442686-31-9 4-[bis-(3,5-dimethyl-phenyl)-phosphanyl]-3-bromo-2,6-dimethoxy-pyridine 
• 74289-57-9 bis-(3,5-dimethylphenyl)chlorophosphine 
• 34696-73-6 3,5-dimethyphenylmagnesium bromide 
• 13445-16-4 3-bromo-2,6-dimethoxypyridine 
• 442905-31-9 4,4'-bis-[bis-(3,5-dimethyl-phenyl)-phosphinoyl]-2,6,2',6'-tetramethoxy-[3,3']bipyridinyl 

Downstream Products

• 1034001-49-4 [RuCl(p-cymene)((R)-xylyl-P-phos)]Cl 

Relevant articles and documents

A new chiral dipyridylphosphine ligand Xyl-P-Phos and its application in the Ru-catalyzed asymmetric hydrogenation of β-ketoesters

A new chiral dipyridylphosphine ligand Xyl-P-Phos has been synthesized and the structure of (S)-Xyl-P-Phos oxide has been characterized by single crystal X-ray diffraction. The ruthenium complex of this ligand, Ru(R-Xyl-P-Phos)(C6H6)Cl2, has been found to be a highly active, enantioselective and air-stable catalyst for the asymmetric hydrogenation of β-ketoesters and shows good potential for industrial applications.