85150-21-6

Basic information

• Product Name: 1-acetyl-1'-diphenylphosphinoferrocene
• CAS NO: 85150-21-6
• Molecular Weight: 412.251
• Mol File: 85150-21-6.mol

Chemical Properties

• CAS DataBase Reference: 1-acetyl-1'-diphenylphosphinoferrocene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-acetyl-1'-diphenylphosphinoferrocene(85150-21-6)
• EPA Substance Registry System: 1-acetyl-1'-diphenylphosphinoferrocene(85150-21-6)

Safety Data

• Hazardous Substances Data: 85150-21-6(Hazardous Substances Data)

Upstream product

• 591-51-5 phenyllithium 
• 75-36-5 acetyl chloride 
• 185223-97-6 1′-(diphenylphosphino)-1-bromoferrocene 
• 78191-00-1 N-Methoxy-N-methylacetamide 

Downstream Products

• 85150-29-4 (C₅H₄P(C₆H₅)2)Fe(C₅H₄C(OH)(CH₃)C₆H₅) 
• 85150-23-8 1-(α-hydroxyethyl)-1'-diphenylphosphinoferrocene 

Relevant articles and documents

Synthesis and characterisation of palladium(ii) complexes with hybrid phosphinoferrocene ligands bearing additional O-donor substituents

While 1,1′-bis(diphenylphosphino)ferrocene (dppf) is widely used as a ligand in coordination chemistry and catalysis, its congeners with oxygen-containing functional groups have long been overlooked. Accordingly, we studied the coordination behaviour in Pd(ii) complexes of three phosphinoferrocene ligands bearing secondary O-donor groups, Ph2PfcR, wherein R = CHO (1), Ac (2) and CMe2(OH) (3), and fc = ferrocene-1,1′-diyl. Depending on the stoichiometry, reactions of 1-3 (L) with [PdCl2(cod)] (cod = η2:η2-cycloocta-1,5-diene) produced the respective mono- and dipalladium complexes, trans-[PdCl2(L-κP)2] and trans-[PdCl(μ-Cl)(L-κP)]2. Compound [PdCl(μ-Cl)(3-κP)]2 was found to dehydrate readily, giving rise to [PdCl(μ-Cl)(Ph2PfcC(Me)═CH2-κP)]2. Furthermore, ligands 1-3 cleaved [(LNC)Pd(μ-Cl)]2 (LNC = 2-((dimethylamino-κN)methyl)phenyl-κC1), yielding [(LNC)PdCl(L-κP)], which were converted into the cationic complexes [(LNC)PdCl(L)]X (L/X = 1/PF6, 2/SbF6, 3/PF6). Compounds with ligands 1 and 2 were structurally authenticated as stable bis-chelate complexes. In contrast, the product featuring ligand 3 was rather unstable and converted into [(LNC)Pd(AcOEt-κO)(3-κP)][PF6] upon recrystallisation. Weak oxygen coordination was confirmed via reactions of [(LNC)PdCl(L)]X with (PhCH2NEt3)Cl in which the parent chloride complexes were regenerated, and this was further corroborated by DFT computations. Our findings, pointing to hemilabile coordination of 1-3, are relevant for catalysis because de-coordination of the weaker binding O-donor moiety may open a vacant site for a substrate, thereby enhancing the catalytic properties of metal complexes with ligands of this type.

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.