145964-33-6

Basic information

• Product Name: (R)-MOP
• Synonyms: R-MOP >=94%;[(R)-2'-Methoxy[1,1'-binaphthalen]-2-yl]diphenylphosphine,99%e.e.;(R)-(+)-2-DIPHENYLPHOSPHINO-2'-METHOXY-1,1'-BINAPHTHYL;(S)-(-)-(DIPHENYLPHOSPHINO)-2'-METHOXY-1,1'-BINAPHTHYL;(R)-(+)-MOP;(R)-MOP;(S)-(-)-2-(DIPHENYLPHOSPHINO)-2'-METHOXY-1,1'-BINAPHTHYL;(S)-2-(DIPHENYLPHOSPHINO)-2'-METHOXY-1,1'-BINAPHTHYL
• CAS NO: 145964-33-6
• Molecular Formula: C₃₃H₂₅OP
• Molecular Weight: 468.52
• Product Categories: Chiral Phosphine;API intermediates;Chiral Reagents
• Mol File: 145964-33-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 177-179°C
• Boiling Point: 584.123 °C at 760 mmHg
• Flash Point: 386.078 °C
• Appearance: white/Powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: almost transparency in Toluene
• Sensitive: air sensitive
• CAS DataBase Reference: (R)-MOP(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-MOP(145964-33-6)
• EPA Substance Registry System: (R)-MOP(145964-33-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 145964-33-6(Hazardous Substances Data)

Usage

Description

(R)-MOP, also known as a phosphine ligand with a bis-naphthalene backbone, is a versatile compound that plays a crucial role in various chemical reactions and processes. It is characterized by its unique structure and ability to enhance the selectivity and efficiency of asymmetric reactions.

Uses

Used in Pharmaceutical Industry:
(R)-MOP is used as a catalyst in the preparation of chiral tetrahydrobenzofuranone alkylideneboronates and oxindoles, which are important intermediates in the synthesis of various pharmaceutical compounds. Its application in this industry is crucial for the development of new drugs and the improvement of existing ones.
Used in Antiviral Drug Synthesis:
(R)-MOP is also used as a catalyst in the total synthesis of Oseltamivir Phosphate (O701000), an orally active inhibitor of influenza virus neuraminidase and an antiviral drug. This application highlights the importance of (R)-MOP in the development of treatments for viral infections.
Used in Asymmetric Reactions:
(R)-MOP is used as a ligand in various asymmetric reactions, such as palladium-catalyzed asymmetric hydrosilylation of olefins, palladium-catalyzed reduction of allylic esters, rhodium-catalyzed asymmetric addition reactions, and asymmetric amination reactions catalyzed by copper(I) complexes. These applications are essential in the synthesis of enantiomerically pure compounds, which are often required in the pharmaceutical, agrochemical, and fragrance industries.

Reactions

1. Efficient catalyst for the enantoselective hydrosilyation of 1-alkenes to optically active 2-alcohols. 2. Ligand for palladium-catalyzed asymmetric reduction of allyltc esters. 3. Ligand for the rhodium-catalyzed asymmetric aryiation of imines with organostannanes. 4. Ligand for the rhodiunvcatalyzed asymmetrk: addition of aryl- and alkenyiborontc acids to Isatins. 5. Ligand for desymmetrizatlon of malonamides via an enantiosetective intramolecular Buchwatd-Hartwig reaction.

Downstream Products

• 639464-80-5 [Pd(acac)((R)-2-(diphenylphosphino)-2'-methoxy-1,1'-binaphthyl)]BF₄ 
• 769174-82-5 [PdCl(C₆H₄CH₂NMe₂)((S)-2-(diphenylphosphino)-2'-methoxy-1,1'-binaphthyl)] 
• 164857-69-6 trans-[PdCl₂[(R)-MeO-MOP]2]*Et₂O