(S)-1',1-bis(diphenylphosphino)-2-(dimethylaminomethyl)ferrocene

Base Information

• Chemical Name: (S)-1',1-bis(diphenylphosphino)-2-(dimethylaminomethyl)ferrocene
• CAS No.: 74286-14-9
• Molecular Formula: C₃₇H₃₅FeNP₂
• Molecular Weight: 611.486
• Mol file: 74286-14-9.mol

Synonyms:

Chemical Property of (S)-1',1-bis(diphenylphosphino)-2-(dimethylaminomethyl)ferrocene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1',1-bis(diphenylphosphino)-2-(dimethylaminomethyl)ferrocene

There total 2 articles about (S)-1',1-bis(diphenylphosphino)-2-(dimethylaminomethyl)ferrocene 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: 65.0%

1,1'-dibromo-2-N,N-dimethylaminomethylferrocene + chloro-diphenylphosphine (1079-66-9,74391-44-9) → rac-2-(N,N-dimethylaminomethyl)-1,1'-bis(diphenylphosphanyl)ferrocene (74286-14-9,409095-06-3) + 1-diphenylphosphino-1’-bromo-2-N,N-dimethylaminomethylferrocene + 1-bromo-1’-diphenylphosphino-2-N,N-dimethylaminomethylferrocene

Guidance literature:

1,1'-dibromo-2-N,N-dimethylaminomethylferrocene; With n-butyllithium; In hexane; at -40 - -10 ℃; for 4h; Schlenk technique; Inert atmosphere;

chloro-diphenylphosphine; In hexane; at -40 - 20 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1021/om400449v

Reference yield:

(S)-1-diphenylphosphino-2-dimethylaminomethyl-3-(trimethylsilyl)ferrocene (74286-48-9) + chloro-diphenylphosphine (1079-66-9,74391-44-9) → (S)-1',1-bis(diphenylphosphino)-2-(dimethylaminomethyl)ferrocene (409095-06-3,74286-14-9)

Guidance literature:

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In diethyl ether; hexane; addition of BuLi in hexane and TMEDA to a soln. of complex, addition ofClPPh2 at 0°C to a stirred mixture, refluxed for 1.5 h, N2 atm.; addition of 30% NaOH at 0°C, extn. (benzene), washing with brine, drying over Na2SO4, evapn., column chromy. (alumina, hexane/benzene 1/1), treatment with t-BuOK in DMSO, preparative TLC (silica gel, benzene/acetone 1/1); elem. anal.;

DOI:10.1246/bcsj.53.1138

Reference yield: 68.0%

diethyl phosphorylchloridite (589-57-1) + rac-2-(N,N-dimethylaminomethyl)-1,1'-bis(diphenylphosphanyl)ferrocene (74286-14-9,409095-06-3) → rac-1-diethoxyphosphanyl-2-N,N-dimethylaminomethyl-3,1'-bis(diphenylphosphanyl)ferrocene (1242240-36-3)

Guidance literature:

With n-C₄H₉Li; In diethyl ether; hexane; (N2); a soln. of n-C4H9Li in n-hexane added slowly to a soln. of Fe complex in Et2O, stirred, cooled to -80°C, ClP(OC2H5)2 added slowly, warmed to room temp.; filtered, evapd., dried (vac., at 50°C), recrystd. from EtOH at -64°C and from n-hexane at -64°C; elem. anal.;

DOI:10.1021/om1004012

upstream raw materials:

chloro-diphenylphosphine

(S)-1-diphenylphosphino-2-dimethylaminomethyl-3-(trimethylsilyl)ferrocene

Downstream raw materials:

2-(acetoxymethyl)-1,1'-bis(diphenylphosphino)ferrocene

rac-1-diethoxyphosphanyl-2-N,N-dimethylaminomethyl-3,1'-bis(diphenylphosphanyl)ferrocene

rac-1-dichlorophosphanyl-2-N,N-dimethylaminomethyl-3,1'-bis(diphenylphosphanyl)ferrocene