55650-58-3

Basic information

• Product Name: (S)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE
• Synonyms: FERROCENE, 1-[1-(DIMETHYLAMINO)ETHYL]-2-(DIPHENYL-PHOSPHINO)-, [R-(R*S*)]-;1(S)-[1(R)-(DIMETHYLAMINO)ETHYL]-2-(DIPHENYL-PHOSPHANY)FERROCENE;(S)-(R)-PPFA;(S)-(+)-N,N-DIMETHYL-1-(2-DIPHENYLPHOSPHINO)FERROCENYLETHYLAMINE;(+)-(S)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE;(S)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE;(+)-(S)-N,N-dimethyl-1-((R)-2-(diphenyl-phosphino;(S,R)-1-(1-dimethylaminoethyl)-2-*(diphenylphosph
• CAS NO: 55650-58-3
• Molecular Formula: C₂₆H₂₈FeNP
• Molecular Weight: 441.33
• EINECS: -0
• Product Categories: Asymmetric Synthesis;Classes of Metal Compounds;Fe (Iron) Compounds;Ferrocenes;Metallocenes;Phosphine Ligands;Synthetic Organic Chemistry;Transition Metal Compounds;Chiral Phosphine
• Mol File: 55650-58-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 141-143°C
• Appearance: /solid
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• CAS DataBase Reference: (S)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE(55650-58-3)
• EPA Substance Registry System: (S)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE(55650-58-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-26-36/37/39-36
• RIDADR: 3288
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 55650-58-3(Hazardous Substances Data)

Usage

Uses

(S)-(+)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine is the raw material of asymmetric hydrogenation chiral ligands.

InChI:InChI=1/C21H22NP.C5H4.Fe/c1-17(22(2)3)20-15-10-16-21(20)23(18-11-6-4-7-12-18)19-13-8-5-9-14-19;1-2-4-5-3-1;/h4-14,16-17H,1-3H3;1-4H;/q2*-1;+2/t17-;;/m0../s1/rC26H26FeNP/c1-20(28(2)3)26-24(27-21-12-10-11-13-21)18-19-25(26)29(22-14-6-4-7-15-22)23-16-8-5-9-17-23/h4-20H,1-3H3/t20-/m0/s1

Upstream product

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

Downstream Products

• 214825-64-6 PdClCH₃(2-(1-dimethylaminoethyl)-1-diphenylphosphinoferrocene) 
• 79767-72-9 PdCl₂<(S)-(R)-PPFA> 
• 74311-58-3 (ScRp)-PPFOAc 
• 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 
• 401913-89-1 Os₃H(CO)8(NO₂)C₅H₅FeC₅H₃CHCH₃N(CH₃)2P(C₆H₅)2 
• 258340-41-9 RuCl(C₈H₁₃)((C₅H₅)Fe(C₂₁H₂₃NP)) 
• 86940-10-5 dichloro(triphenylphosphine)(1-(N,N-α-dimethylaminoethyl)-2-diphenylphosphino-ferrocene)ruthenium(II) 

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.