224311-51-7

Basic information

• Product Name: 2-(Di-tert-butylphosphino)biphenyl
• Synonyms: BIPHENYL-2-YL-DI-TERT-BUTYL-PHOSPHANE;(2-biphenyl)di-tert-butylphosphine;(2-BIPHENYLYL)DI-TERT-BUTYLPHOSPHINE;2-(DI-TERT-BUTYLPHOSPHINO)BIPHENYL;2-(DI-T-BUTYLPHOSPHINO)BIPHENYL;2-(Di-t-butylphosphino)biphenyl,99%JohnPhos;2-(Di-t-butylphosphine) biphenyl;PHOSPHINE, [1,1''-BIPHENYL]-2-YLBIS(1,1-DIMETHYLETHYL)-
• CAS NO: 224311-51-7
• Molecular Formula: C₂₀H₂₇P
• Molecular Weight: 298.4
• EINECS: -0
• Product Categories: Benzene derivatives;Phosphines;Ligand;Phosphine Ligands;Synthetic Organic Chemistry;organophosphine ligand;Achiral Phosphine;Aryl Phosphine;Buchwald Ligands Series;Buchwald Ligands&Precatalysts
• Mol File: 224311-51-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 86-88 °C(lit.)
• Boiling Point: 405.5 °C at 760 mmHg
• Flash Point: 210.1 °C
• Appearance: White/Crystals or Crystalline Powder
• Density: 1 g/cm3
• Vapor Pressure: 2.05E-06mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly, Heated, Sonic
• Water Solubility: Insoluble
• Stability: Air Sensitive
• BRN: 8322131
• CAS DataBase Reference: 2-(Di-tert-butylphosphino)biphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Di-tert-butylphosphino)biphenyl(224311-51-7)
• EPA Substance Registry System: 2-(Di-tert-butylphosphino)biphenyl(224311-51-7)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26-22
• WGK Germany: 3
• F: 10-23
• TSCA: No
• HazardClass: AIR SENSITIVE
• Hazardous Substances Data: 224311-51-7(Hazardous Substances Data)

Usage

Reactions

Ligand used in the palladium-catalyzed synthesis of aromatic amines from aryl chlorides, bromides and triflates. Ligand employed in a very active and general catalyst for Suzuki coupling reactions using aryl chlorides, bromides and triflates. Ligand used in palladium-catalyzed synthesis of oxindoles from α-chloroacetanilides. Effective ligand used in palladium-catalyzed arylation of thiazoles. Used in the formation of 2-benzylindolines via sequential palladium-catalyzed N-arylation/cyclization/C-arylation. Selective in the palladium-catalyzed arylation of silyl enol ethers formed from copper-catalyzed reduction of enones.

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 224311-51-7 differently. You can refer to the following data:
1. suzuki reaction
2. 2-(Di-tert-butylphosphino)biphenyl (also known as JohnPhos) is a Buchwald ligand that is highly efficient in palladium-catalyzed reactions.

General Description

JohnPhos is a Buchwald′s sterically bulky biaryl phosphine ligand. It is a reactive dialkylbiaryl phosphine ligand which catalyzes the carbon-nitrogen bond-forming reactions. Coordination chemistry of gold catalysts bearing JohnPhos as ligand has been investigated by NMR spectroscopy.

InChI:InChI=1/C20H27P/c1-19(2,3)21(20(4,5)6)18-15-11-10-14-17(18)16-12-8-7-9-13-16/h7-15H,1-6H3

Upstream product

• 583-55-1 1-Bromo-2-iodobenzene 
• 98-80-6 phenylboronic acid 
• 2052-07-5 2-Bromobiphenyl 
• 819-19-2 di-tert-butylphosphine 
• 583-53-9 2,3-dibromobenzene 
• 17763-65-4 biphenyl-2-yl trifluoromethanesulfonate 
• 13716-10-4 di(tert-butyl)chlorophosphine 
• 82214-69-5 2-biphenylmagnesium bromide 
• 1336-21-6 ammonium hydroxide 

Downstream Products

• 425638-72-8 [3-(4-Methyl-piperazin-1-yl)-5,6,7,8-tetrahydro-naphthalen-1-yl]-acetic Acid Ethyl Ester 
• 404011-08-1 1-(2,6-dihydroxy-4-morpholin-4-yl-phenyl)-ethanone 
• 2928-43-0 2-biphenylmethanol 
• 171092-38-9 3-(pyridin-3-yl)acetophenone 
• 92-91-1 biphenyl-4-acetaldehyde 
• 1625-92-9 4-tert-butylbiphenyl 
• 644-08-6 4-Methylbiphenyl 
• 92495-53-9 2-methoxy-4'-methylbiphenyl 
• 2920-38-9 4-cyano-1,1'-biphenyl 
• 4075-79-0 4-phenylacetanilide 
• 92-69-3 4-Phenylphenol 
• 92-93-3 1-phenyl-4-nitrobenzene 
• 3976-34-9 2,6-dimethyl-1,1′-biphenyl 
• 405308-05-6 dimethyl 2-(3,4-dimethylphenyl)malonate 

Relevant articles and documents

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

A preparation method of compound phosphine benzene apperception (by machine translation)

The invention relates to a method for preparing phosphine benzene apperception compound, the bromine compound is made with the magnesium reaction of Grignard reagent, then using four (triphenylphosphine) palladium-catalyzed bromophenylacetic compound phosphine chlorination reaction with the Grignard reagent. The specific method is, under the protection of inert gas, the bromo compound is made with the magnesium chips and organic solvent Grignard reagent, reflux 2 the [...] 10 hours; joined four at room temperature (triphenylphosphine) palladium, stirring 10 minutes to 3 hours, chlorinated room temperature instillment phosphine composition, reflux reaction the 1 [...] 10 hours; in the ice water bath in the fluid adds by drops full and weak acid to the reaction under weak alkali salt-water solution, liquid, organic phase exsolution, alcohol solvent crystallization, filtering to obtain compound phosphine benzene. The preparation method of this invention not only greatly improves manufacturing yield, and after treatment is simple, the process of repeated washing with ammonia water, the manufacturing process is simplified, is beneficial for large-scale industrial production. (by machine translation)

Process for producing biarylphosphine compound

A process for producing a biarylphosphine compound is disclosed. The process has a step of subjecting a biarylsulfonate compound to coupling reaction with a hydrogen-phosphine compound in the presence of a catalyst and an organic strong base to obtain a biarylphosphine compound. As the catalyst, preferably used is a nickel compound or a palladium compound. As the organic strong base, preferably used is 1,8-diazabicyclo[5.4.0]undecene-7 (DBU).