1070663-78-3

Basic information

• Product Name: 2-(Dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl, min. 98% BrettPhos
• Synonyms: 2-(Dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl, min. 98% BrettPhos;2-(Dicyclohexylphosphino)3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl;Dicyclohexyl(2',4',6'-triisopropyl-3,6-diMethoxy-[1,1'-biphenyl]-2-yl)phosphine;Dicyclohexyl[3,6-dimethoxy-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine;2-(Dicyclohexylphosphino)-3,6-diMethoxy-2'-4' -6'-tri-i-propyl-1,1'-biphenyl;2-Dicyclohexylphosphino-2',4',6'-triisopropyl-3,6-diMethoxybiphenyl, 97+%;2-Dicyclohexylphosphino-2',4',6'-tri-i-propyl-3,6-diMethoxy-1,1'-biphenyl, 98% (BrettPhos);BrettPhos 96%
• CAS NO: 1070663-78-3
• Molecular Formula: C₃₅H₅₃O₂P
• Molecular Weight: 536.767881
• Product Categories: Achiral Phosphine;Aryl Phosphine;Buchwald Ligands Series;Buchwald Ligands&Precatalysts
• Mol File: 1070663-78-3.mol

Chemical Properties

• Melting Point: 191-193℃
• Boiling Point: 607.671 °C at 760 mmHg
• Flash Point: 404.5 °C
• Appearance: white/crystal
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: 2-(Dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl, min. 98% BrettPhos(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl, min. 98% BrettPhos(1070663-78-3)
• EPA Substance Registry System: 2-(Dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl, min. 98% BrettPhos(1070663-78-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-37-60
• WGK Germany: nwg
• TSCA: No
• Hazardous Substances Data: 1070663-78-3(Hazardous Substances Data)

Usage

Uses

Used in Cross-Coupling Reactions:
2-(Dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl, min. 98% BrettPhos is used as a ligand for the Suzuki-Miyaura coupling of tosylates and mesylates. Its unique steric and electronic properties enable efficient coupling reactions, leading to the formation of carbon-carbon bonds in a wide range of organic compounds.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-(Dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl, min. 98% BrettPhos is utilized as a Buchwald phosphine ligand. Its strong electron-donating ability and bulky substituents make it an effective ligand for various palladium-catalyzed reactions, such as C-N and C-O bond formations, which are crucial for the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
2-(Dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl, min. 98% BrettPhos is used as a ligand in the synthesis of complex pharmaceutical molecules. Its ability to facilitate challenging cross-coupling reactions allows for the efficient production of biologically active compounds, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical industry, 2-(Dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl, min. 98% BrettPhos is employed as a ligand for the synthesis of active ingredients in pesticides and herbicides. Its role in facilitating key chemical reactions enables the production of more effective and targeted agrochemicals, promoting sustainable agriculture and crop protection.
Overall, 2-(Dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl, min. 98% BrettPhos is a valuable ligand with a wide range of applications in various industries, particularly in the synthesis of complex organic compounds and the development of new pharmaceuticals and agrochemicals.

Reactions

Ligand for palladium-catalyzed cross-coupling reactions using aryl mesylates with electron-deficient anilines. Ligand for palladium-catalyzed cross-coupling of primary arylamines at low catalyst loading. Ligand for palladium-catalyzed cross-coupling of aryl iodides and primary amines. Ligand for the Suziki-Miyaura coupling of tosylates and mesylates. Ligand for the palladium-catalyzed trifluoromethylation of aryl chlorides. Ligand for the palladium-catalyzed formation of aryl-SCF3 compounds from aryl bromides. Ligand for the nickel-catalyzed cross-coupling of styrenyl epoxides with boronic acids. Ligand for the palladium-catalyzed intramolecular CH difluoroalkylation.

InChI:InChI=1S/C35H53O2P/c1-23(2)26-21-29(24(3)4)33(30(22-26)25(5)6)34-31(36-7)19-20-32(37-8)35(34)38(27-15-11-9-12-16-27)28-17-13-10-14-18-28/h19-25,27-28H,9-18H2,1-8H3

Upstream product

• 13716-10-4 di(tert-butyl)chlorophosphine 
• 1402393-56-9 2-bromo-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl 
• 108894-99-1 (2,4,6-triisopropylphenyl)magnesium bromide 
• 82830-49-7 2-fluoro-1,4-dimethoxybenzene 
• 16523-54-9 chlorodicyclohexylphosphane 
• 1070663-76-1 2-iodo-2’,4’,6’-triisopropyl-3,6-dimethoxybiphenyl 

Downstream Products

• 1070664-36-6 PdCl(P(C₆H₁₁)2(C₆H₂(OCH₃)2C₆H₂(CH(CH₃)2)3))(C₆H₅) 
• 1070664-36-6 PdCl(P(C₆H₁₁)2(C₆H₂(OCH₃)2C₆H₂(CH(CH₃)2)3))(C₆H₅) 
• 1070664-38-8 PdBr(P(C₆H₁₁)2(C₆H₂(OCH₃)2C₆H₂(CH(CH₃)2)3))(C₆H₃(CH₃)2) 
• 1070664-38-8 PdBr(P(C₆H₁₁)2(C₆H₂(OCH₃)2C₆H₂(CH(CH₃)2)3))(C₆H₃(CH₃)2) 
• 1070664-34-4 PdBr(P(C₆H₁₁)2(C₆H₂(OCH₃)2C₆H₂(CH(CH₃)2)3))(C₆H₅) 
• 1070664-34-4 PdBr(P(C₆H₁₁)2(C₆H₂(OCH₃)2C₆H₂(CH(CH₃)2)3))(C₆H₅) 
• 1599466-83-7 C₄₉H₆₈NO₅PPdS 
• 1599466-84-8 C₅₄H₇₀NO₅PPdS 

Relevant articles and documents

PRODUCTION METHOD OF BIARYLPHOSPHINE

A production method by which a biarylphosphine useful as a Buchwald phosphine ligand can be obtained in high purity is provided through an industrially advantageous process. The production method of a biarylphosphine comprises a step A of reacting a lithiated product obtained through lithiation of a halogenated benzene derivative with a benzene derivative to obtain a biphenyl derivative, and a step B of the reacting the biphenyl derivative with a halogenated phosphine. In the step A, the charge molar ratio of the halogenated benzene derivative to the benzene derivative is preferably 1.0 to 5.0.

Method for synthesizing large-steric-hindrance biphenyl organic phosphine compound

The invention discloses a method for synthesizing a large-steric-hindrance biphenyl organic phosphine compound, relates to a synthesis method of 2-dialkylphosphine-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl, and belongs to the field of organic synthesis. In a water-free oxygen-free atmosphere, dialkyl phosphine chloride is used as a raw material to react with magnesium to generate dialkyl phosphine magnesium chloride, and then dialkyl phosphine magnesium chloride reacts with 2-halo-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl under the action of a nickel catalyst to generate 2-dialkylphosphine-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl. Compared with the prior art, the method has the advantages of mild reaction conditions, high yield and simple post-treatment, and is suitable for industrial production.

An improved synthesis of brettphos- and rockphos-type biarylphosphine ligands

Improved processes for the preparation of biphenyl-based phosphine ligands t-BuBrettPhos, RockPhos, and BrettPhos are presented. The new methods, featuring the use of Grignard reagents and catalytic amounts of copper, are superior to the previous methods, which require the use of tert-butyllithium and stoichiometric amounts of copper. Specifically, the use of less dangerous reagents provides a safer process, while the use of catalytic amounts of copper allows for the isolation of pure products in high yield. These improvements are particularly significant for the large-scale preparation of these ligands. Copyright

LIGANDS FOR TRANSITION-METAL-CATALYZED CROSS-COUPLINGS, AND METHODS OF USE THEREOF

Ligands for transition metals are disclosed herein, which may be used in various transition-metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The disclosed methods provide improvements in many features of the transition-metal-catalyzed reactions, including the range of suitable substrates, number of catalyst turnovers, reaction conditions, and efficiency. For example, improvements have been realized in transition-metal-catalyzed cross-coupling reactions.

A highly active catalyst for Pd-catalyzed amination reactions: Cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides

A catalyst system based on a new biarylmonophosphine ligand (BrettPhos) that shows excellent reactivity for C-N cross-coupling reactions is reported. This catalyst system enables the use of aryl mesylates as a coupling partner in C-N bond-forming reactions. Additionally, the use of BrettPhos permits the highly selective monoarylation of an array of primary aliphatic amines and anilines at low catalyst loadings and with fast reaction times, including the first monoarylation of methylamine. Lastly, oxidative addition complexes of BrettPhos are included, which provide insight into the origin of reactivity for this system. Copyright