2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Base Information

• Chemical Name: 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl
• CAS No.: 657408-07-6
• Molecular Formula: C26H35O2P
• Molecular Weight: 410.536
• Hs Code.: 2922299090
• Mol file: 657408-07-6.mol

Synonyms:(2,6-Dimethoxy-1,1'-biphenyl-2-yl)dicyclohexylphosphine;2-(Dicyclohexylphosphino)-2',6'-dimethoxy-1,1'-biphenyl;Dicyclohexyl(2',6'-dimethoxybiphenyl-2-yl)phosphine;S-Phos;

Chemical Property of 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Chemical Property:

• Melting Point: 164-166 °C
• Boiling Point: 513.3 °C at 760 mmHg
• Flash Point: 330.7 °C
• PSA: 32.05000
• LogP: 7.14340
• Storage Temp.: Refrigerated.
• Sensitive.: Air Sensitive
• Solubility.: soluble in Chloroform

Purity/Quality:

98% ^*data from raw suppliers

S-Phos ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 24/25-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Uses: SPhos [2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.? SPhos may be used as a ligand in the following processes: ??Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between Boc-protected aminomethyltrifluoroborate and aryl chlorides or hetaryl chlorides to form the corresponding aminomethylarenes.??Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between 4-methyl-substituted piperidinylzinc reagent and different aryl or heteroaryl iodides to form various substituted piperidines.??Intramolecular Suzuki-Miyaura coupling to form the 18-membered macrocyclic ring during the multi-step synthesis of riccardin C. Utilized in conjunction with palladium to form a highly active catalyst for C-N bond formation. Highly universal ligand for Suzuki-Miyaura coupling; aryl chlorides, hindered biaryls, heterobiaryls. S-Phos is a catalyst that is used in the preparation of thiadiazoles as DGAT1 inhibitors with potential in metabolic diseases treatment. suzuki reaction

Technology Process of 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

There total 12 articles about 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

chlorodicyclohexylphosphane (16523-54-9) + 2'-bromo-2,6-dimethoxybiphenyl (755017-61-9) → dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane (657408-07-6)

Guidance literature:

2'-bromo-2,6-dimethoxybiphenyl; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1.5h; Inert atmosphere; Cooling with acetone-dry ice;

chlorodicyclohexylphosphane; In tetrahydrofuran; at 20 - 45 ℃; Inert atmosphere;

DOI:10.1002/anie.200901643

Reference yield: 87.0%

(2’,6’-dimethoxy-[1,1’-biphenyl]-2-yl)dicyclohexylphosphine oxide → dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane (657408-07-6)

Guidance literature:

With 1,3-diphenyl-disiloxane; In toluene; at 110 ℃; chemoselective reaction; Sealed tube;

DOI:10.1002/chem.201703875

Reference yield: 48.0%

2'-chloro-2,6-dimethoxy-1,1'-biphenyl (1380028-15-8) + chlorodicyclohexylphosphane (16523-54-9) → dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane (657408-07-6)

Guidance literature:

2'-chloro-2,6-dimethoxy-1,1'-biphenyl; With sec.-butyllithium; In diethyl ether; cyclohexane; at -78 - -45 ℃; Inert atmosphere;

chlorodicyclohexylphosphane; In diethyl ether; cyclohexane; at -78 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201200160

upstream raw materials:

chlorodicyclohexylphosphane

2'-bromo-2,6-dimethoxybiphenyl

2-bromo-1-chlorobenzene

1,3-Dimethoxybenzene

Downstream raw materials:

Pd(2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl)₂Cl₂

(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)Pd(Ph)(μ-Cl))2

chloro(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)[2-(2-aminoethylphenyl)]palladium(II)

3-(2,6-diphenylphenyl)-6,7-dimethylimidazo[1,2-f]phenanthridine

Refernces

• 1、 Buonomo, Joseph A.,Eiden, Carter G.,Aldrich, Courtney C.. "Chemoselective Reduction of Phosphine Oxides by 1,3-Diphenyl-Disiloxane". supporting information. p. 14434 - 14438. Retrieved 2017/10/23.
• 2、 Truong, Thanh,Mesgar, Milad,Le, Ky Khac Anh,Daugulis, Olafs. "General method for functionalized polyaryl synthesis via aryne intermediates". . p. 8568 - 8576. Retrieved 2014/07/07.