108280-65-5

Basic information

• Product Name: 1,1'-Bis(phosphino)ferrocene,
• Synonyms: 1,1'-Bis(phosphino)ferrocene,
• CAS NO: 108280-65-5
• Molecular Formula: C₁₀H₁₂FeP₂
• Molecular Weight: 241.93
• Mol File: 108280-65-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,1'-Bis(phosphino)ferrocene,(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-Bis(phosphino)ferrocene,(108280-65-5)
• EPA Substance Registry System: 1,1'-Bis(phosphino)ferrocene,(108280-65-5)

Safety Data

• Hazardous Substances Data: 108280-65-5(Hazardous Substances Data)

Usage

General Description

1,1'-Bis(phosphino)ferrocene is a chemical compound that consists of a ferrocene core with two phosphine groups attached to the cyclopentadienyl rings. It is commonly used as a ligand in organometallic chemistry, serving as a stabilizing agent for transition metal complexes. The compound’s symmetric and rigid structure allows for the formation of stable and selective metal complexes, making it a valuable tool for catalytic reactions in asymmetric synthesis and other industrial processes. Its unique properties have also made it a popular choice in materials science and chemical research, where its stability and reactivity can be leveraged for a variety of applications.

Upstream product

• 7732-18-5 water 
• 16853-85-3 lithium aluminium tetrahydride 
• 399043-68-6 1,1'-ferrocenyl-bis(diethylphosphonate) 
• 911141-76-9 1,1'-ferrocenediyl bis(dibromophosphane) 

Downstream Products

• 866394-07-2 (S,S)-f-binaphane 

Relevant articles and documents

'User-friendly' primary phosphines and an arsine: Synthesis and characterization of new air-stable ligands incorporating the ferrocenyl group

Reaction of FcCH2CH2P(O)(OH)2 or FcCH2P(O)(OH)(OEt) [Fc = FcCH2CH2PH2 and the previously reported analogue FcCH2PH2 in high yields. Reduction of 1,1′-Fc'[CH'2P(O)(OEt)2][Fc' = Fe(η5-C5H4)2] and 1,2-Fc″[CH2P(O)(OEt)2] [Fc″ = Fe(η5 -C5H5) (η5-C5H3)] similarly gives the new primary phosphines 1,1′-Fc'(CH2PH2)2 and 1,2-Fc″ (CH2PH2)2, respectively. The arsine FcCH2CH2AsH2, which is also air-stable, has been prepared by reduction of the arsonic acid FcCH2CH2As(O)(OH)2 using Zn/HCl. An X-ray structure has been carried out on the arsine, which is only the second structure determination of a free primary arsine. The molybdenum carbonyl complex [1,2-Fc″(CH2PH2)2Mo(CO)4] was prepared by reaction of the phosphine with [Mo(CO)4(pip)2] (pip = piperidine), and characterized by a preliminary X-ray structure determination. However, the same reaction of 1,1′-Fc'(CH2PH2)2 with [Mo(CO)4(pip)2] gave [1,1′-Fc'(CH2PH2)2Mo(CO)4] and the dimer [1,1′-Fc'(CH2PH2)2Mo(CO)4] 2, characterized by electrospray mass spectrometry. 1,1′-Fc'[CH2PH2Mo(CO)5]2 and 1,2-Fc″[CH2PH2Mo(CO)5]2 were likewise prepared from the phosphines and excess [Mo(CO)5(THF)].

The homologous series of 1,1′-ferrocenylenebisdihalophosphanes (C5H4PX2)2Fe (X = F, Cl, Br, I): Precursors for the first metallocene bridged bisphosphaalkene

A facile synthetic access to the homologous series of 1,1′- ferrocenylene bisdihalophosphanes Fc′(PX2)2 (X = F, Cl, Br, I; Fc′ = 1,1′-ferrocenediyl = ferrocenylene = -C 5H4FeC5H4-) is reported. The 31P NMR spectroscopic data of this series suggest a similar electronic interaction of the -PX2 unit with the ferrocene system as in monofunctional ferrocenyldihalophosphanes. Crystal structures for Fc′(PCl2)2 and Fc′(PBr2) 2 reveal that the nature of the halogen atom within the phosphane unit strongly influences the twist angle of the ferrocene system, while leaving the other structural parameters mostly unaffected. Based on these bisdihalophosphanes, a synthetic access to the first metallocene bridged bisphosphaalkene ((C5H4PC(t-Bu)OTMS)2Fe) is reported in which the tert-butyl substituents provide sufficient steric pressure to control the E/Z isomeric ratio which leads to the almost exclusive formation of the most stable Z,Z isomer out of the three possible isomers. The Royal Society of Chemistry 2006.

Chiral phospholanes via chiral 1,4-diol cyclic sulfates

This invention relates to novel chiral 1,4-diol cyclic sulfates and their use as precursors in the preparation of chiral phospholane ligands, and chiral complexes useful as catalysts for carrying out enantioselective reactions.