1070663-78-3 Usage
Description
2-(Dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl, min. 98% BrettPhos is a phosphine ligand with a unique structure that features a dicyclohexylphosphino group, a biphenyl core with methoxy and tri-isopropyl substituents. This complex structure endows BrettPhos with specific properties that make it a versatile and efficient ligand in various chemical reactions.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 1070663-78-3 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,0,7,0,6,6 and 3 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1070663-78:
(9*1)+(8*0)+(7*7)+(6*0)+(5*6)+(4*6)+(3*3)+(2*7)+(1*8)=143
143 % 10 = 3
So 1070663-78-3 is a valid CAS Registry Number.
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
1070663-78-3Relevant articles and documents
PRODUCTION METHOD OF BIARYLPHOSPHINE
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, (2022/06/03)
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
Hoshiya, Naoyuki,Buchwald, Stephen L.
, p. 2031 - 2037 (2012/10/08)
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
Fors, Brett P.,Watson, Donald A.,Biscoe, Mark R.,Buchwald, Stephen L.
supporting information; body text, p. 13552 - 13554 (2009/02/06)
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
