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

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

Uses

Used in Pharmaceutical Industry:
2-(Di-tert-butylphosphino)biphenyl is used as a catalyst in the Suzuki reaction for the synthesis of biologically active compounds and pharmaceuticals. Its high efficiency and selectivity make it a valuable tool in the development of new drugs and drug candidates.
Used in Chemical Synthesis:
2-(Di-tert-butylphosphino)biphenyl is used as a ligand in palladium-catalyzed reactions for the formation of carbon-nitrogen bonds. This application is crucial in the synthesis of various organic compounds, including those with potential applications in materials science, agrochemicals, and other industries.
Used in Coordination Chemistry:
2-(Di-tert-butylphosphino)biphenyl is used as a ligand in the study of gold catalysts' coordination chemistry. Its unique steric properties and reactivity make it an interesting candidate for understanding the structure and function of gold catalysts in various chemical processes.

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.

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

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

Downstream Products

• 92-91-1 biphenyl-4-acetaldehyde 
• 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 
• 2142-66-7 1-([1,1'-biphenyl]-2-yl)ethanone 
• 403612-06-6 2-methyl-2-(4-{2-[5-methyl-2-(4-phenoxy-phenyl)-oxazol-4-yl]-ethoxy}-phenoxy)-propionic acid ethyl ester 
• 403612-07-7 2-Methyl-2-(4-{2-[5-methyl-2-(3-phenoxy-phenyl)-oxazol-4-yl]-ethoxy}-phenoxy)-propionic Acid Ethyl Ester 
• 405308-05-6 dimethyl 2-(3,4-dimethylphenyl)malonate 
• 854045-93-5 2-(di-tert-butylphosphino)-1,1'-biphenylgold(I) chloride 
• 19853-10-2 2-(biphenyl-2-yl)acetonitrile 
• 644-08-6 4-Methylbiphenyl 
• 92495-53-9 2-methoxy-4'-methylbiphenyl 
• 1625-92-9 4-tert-butylbiphenyl 

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.

Synthesis of di-tert-butylphenol [...] biphenyl compounds (by machine translation)

The invention discloses a method for synthesizing tert-[...] biphenyl compounds, which belongs to the field of organic synthesis. In the oxygen free atmosphere, in order to di-tert-butylphenol [...] as raw material, under the action of the palladium catalyst, with the O-bromophenylacetic reaction, then the obtained by coupling with aryl boric acid di-tert-butylphenol [...] biphenyl compound. Compared with the prior art the invention less reaction steps, the operation is simple, high yield, is more suitable for industrial production. (by machine translation)

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)

Palladium-catalyzed P(O)R2 directed C-H arylation to synthesize electron-rich polyaromatic monophosphorus ligands

Palladium-catalyzed arylation of (diisopropylphosphoryl)biphenyl skeleton derivatives by the P(O)R2 directed C-H functionalization was reported. The related products were obtained in high regioselectivity and good functional group tolerance was observed. This reaction provided a new and efficient pathway for the synthesis of polyaromatic monophosphorus ligands. The Royal Society of Chemistry.

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).

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.

PROCESS FOR PRODUCING TERTIARY PHOSPHINE HAVING BULKY HYDROCARBON GROUP BONDED

The present invention provides a production process by which tertiary phosphine with an attached sterically bulky hydrocarbon group, said tertiary phosphine being useful as a ligand of a transition metal catalyst in organic synthesis reactions, can be produced in a high yield and with high purity on an industrial scale through simple and safe operations. The present invention comprises allowing a dialkylphosphinous halide to react with a Grignard reagent in the presence of a copper compound in an amount corresponding to 0.1 to 5% by mol based on the dialkylphosphinous halide to produce tertiary phosphine represented by the following formula (3) : wherein R1 and R2 are each a tertiary hydrocarbon group of 4 to 13 carbon atoms, and R3 is an alkyl group, an alkenyl group, an aryl group or the like.

Ligands for metals and improved metal-catalyzed processes based thereon

One aspect of the present invention relates to novel 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.

Highly active palladium catalysts for Suzuki coupling reactions

Mixtures of palladium acetate and o-(di-tert-butylphosphino)biphenyl (4) catalyze the room-temperature Suzuki coupling of aryl bromides and aryl chlorides with 0.5-1.0 mol % Pd. Use of o-(dicyclohexylphosphino)biphenyl (2) allows Suzuki couplings to be carried out at low catalyst loadings (0.000001-0.02 mol % Pd). The process tolerates a broad range of functional groups and substrate combinations including the use of sterically hindered substrates. This is the most active catalyst system in terms of reaction temperature, turnover number, and steric tolerance which has been reported to date.

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.