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
• Article Data: 5

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

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.

Uses

Different sources of media describe the Uses of 1070663-78-3 differently. You can refer to the following data:
1. Ligand for the Suziki-Miyaura coupling of tosylates and mesylates.
2. Buchwald Phosphine Ligands for chemical Synthesis

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

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

Downstream Products

• 1334547-75-9 chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl]gold (I) 

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.

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

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