224311-55-1

Basic information

• Product Name: [1,1′-Biphenyl]-2-yldi[(3S,5S,7S)-1-adamantanyl]phosphine
• Synonyms: (2-Biphenyl)di-1-adamantylphosphine;[1,1′-Biphenyl]-2-yldi[(3S,5S,7S)-1-adamantanyl]phosphine;(2-Biphenyl)di-1-adamantylphosphine 97%
• CAS NO: 224311-55-1
• Molecular Formula: C32H39P
• Molecular Weight: 454.63
• Mol File: 224311-55-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 220-225°C
• Appearance: /
• CAS DataBase Reference: [1,1′-Biphenyl]-2-yldi[(3S,5S,7S)-1-adamantanyl]phosphine(CAS DataBase Reference)
• NIST Chemistry Reference: [1,1′-Biphenyl]-2-yldi[(3S,5S,7S)-1-adamantanyl]phosphine(224311-55-1)
• EPA Substance Registry System: [1,1′-Biphenyl]-2-yldi[(3S,5S,7S)-1-adamantanyl]phosphine(224311-55-1)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 36/37/39-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 224311-55-1(Hazardous Substances Data)

Usage

Uses

Phosphine ligand for cross coupling.

Upstream product

• 57680-77-0 adamantylmagnesium bromide 
• 82214-69-5 2-biphenylmagnesium bromide 
• 2052-07-5 2-Bromobiphenyl 
• 157282-19-4 di-1-adamantylchlorophosphane 

Relevant articles and documents

Ligands for metals and improved metal-catalyzed processes based thereon

One aspect of the present invention relates to ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in transition metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.

Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers

A general method for the palladium-catalyzed formation of diaryl ethers is described. Electron-rich, bulky aryldialkylphosphine ligands, in which the two alkyl groups are either tert-butyl or 1-adamantyl, are the key to the success of the transformation. A wide range of electron-deficient, electronically neutral and electron-rich aryl bromides, chlorides, and triflates can be combined with a variety of phenols with the use of sodium hydride or potassium phosphate as base in toluene at 100 °C. The bulky yet basic nature of the phosphine ligand is thought to be responsible for increasing the rate of reductive elimination of the diaryl ether from palladium.