74311-54-9

Basic information

• Product Name: (-)-(R)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE
• Synonyms: (-)-(R)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE;(2S)-1-[(1R)-1-(dimethylamino)ethyl]-2-(diphenylphosphino)-Ferrocene;(2S)-1-[(1R)-1-(Dimethylamino)ethyl]-2-(diphenylphosphino)ferrocene,99%e.e.
• CAS NO: 74311-54-9
• Molecular Formula: C₂₆H₂₈FeNP
• Molecular Weight: 435.29
• Mol File: 74311-54-9.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: (-)-(R)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(R)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE(74311-54-9)
• EPA Substance Registry System: (-)-(R)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE(74311-54-9)

Safety Data

• Hazardous Substances Data: 74311-54-9(Hazardous Substances Data)

Usage

Uses

Used in Catalytic Asymmetric Synthesis:
(-)-(R)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE is utilized as a chiral ligand for catalytic asymmetric synthesis, enabling the production of enantiomerically pure compounds. Its application is crucial in creating compounds with specific stereochemistry, which is essential for the effectiveness, selectivity, and reduction of side effects in pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (-)-(R)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE is employed for the development of new drugs with improved efficacy and selectivity. Its role in creating enantiomerically pure compounds is vital for ensuring that drugs target specific biological pathways without affecting others, thereby reducing potential side effects.
Used in Agrochemical Industry:
(-)-(R)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE is also used in the agrochemical industry for the synthesis of enantiomerically pure pesticides and herbicides. The ability to control the stereochemistry of these compounds allows for the development of more effective and environmentally friendly agrochemicals with reduced off-target effects.
Used in Research and Development:
In the field of research and development, (-)-(R)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE serves as an important tool for exploring new synthetic methodologies and understanding the role of stereochemistry in chemical reactions. Its unique properties make it a valuable asset in advancing scientific knowledge and innovation in organic chemistry.

Upstream product

• 83560-65-0 [2-(α-(dimethylamino)ethyl)-1,1'-ferrocenediyl]phenylphosphine 
• 591-51-5 phenyllithium 

Downstream Products

• 401913-89-1 Os₃H(CO)8(NO₂)C₅H₅FeC₅H₃CHCH₃N(CH₃)2P(C₆H₅)2 
• 193815-90-6 Pd((C₅H₅)Fe(C₅H₃(CH(CH₃)N(CH₃)2)P(C₆H₅)2))(C₄H₂O₃) 
• 193815-95-1 [Pd(η(3)-2-Me-C3H4)Pd((C5H5)Fe(C5H3(CH(Me)NMe2)P(C6H5)2))]OSO2CF3 
• 214825-64-6 PdClCH₃(2-(1-dimethylaminoethyl)-1-diphenylphosphinoferrocene) 
• 86940-10-5 dichloro(triphenylphosphine)(1-(N,N-α-dimethylaminoethyl)-2-diphenylphosphino-ferrocene)ruthenium(II) 
• 74311-58-3 (ScRp)-PPFOAc 
• 258340-41-9 RuCl(C₈H₁₃)((C₅H₅)Fe(C₂₁H₂₃NP)) 

Relevant articles and documents

The synthesis of α-N,N-dimethyl-1'-diphenylphosphinoferrocenylethylamine and related ligands

Routes to the title compound were explored based on the cleavage of -ferrocenophanes with aryllithium.Thus the cleavage of (ν5-C5H4)Fe(ν5-C5H3(CHMeNMe2)PPh) with phenyllithium affords (ν5-C5H4Li)Fe(ν5-C5H3(CHMeNMe2)PPh2) and (ν5-C5H4PPh2)Fe(ν5-C5H3Li(CHMeNMe2)) in the ratio 15:85.Hydrolysis of this mixture affords the title compound 4.The lithio-ferrocenes can be treated with XER2 to yield other mixed ligands (E = As, P).A route to 4 via (ν5-C5H4PPh2)Fe(ν5-C5H4C(O)Me) was also established but it is complicated by low yields and many side products such as 5-C5H4PPh2)Fe(ν5-C5H4)>2C=CH2.