(S)-(+)-N,N-Dimethyl-1-[(2-diphenylphosphino)ferrocenyl]ethylamine
[CAS# 55650-58-3]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: (S)-(+)-N,N-Dimethyl-1-[(2-diphenylphosphino)ferrocenyl]ethylamine
• Molecular Formula: C₂₆H₂₈FeNP
• Molecular Weight: 441.33
• CAS Registry Number: 55650-58-3
• EC Number: 678-897-9
• SMILES: CC(c1cc[cH-]c1P(c2ccccc2)c3ccccc3)N(C)C.[cH-]1cccc1.[Fe+2]

Properties

• Melting point: 141-143 ºC
• alpha: 355 º (c=0.6 in EtOH)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H332-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332

Discovory and Applicatios

(S)-(+)-N,N-Dimethyl-1-[(2-diphenylphosphino)ferrocenyl]ethylamine, commonly known as (S)-(+)-DMPF, is a sophisticated organophosphorus compound with significant applications in asymmetric synthesis and catalysis. This compound features a ferrocenyl moiety, which enhances its utility in various chemical transformations. The following article provides an overview of the discovery, synthesis, and applications of (S)-(+)-DMPF.

The discovery of (S)-(+)-DMPF emerged from the growing interest in organophosphorus compounds and their role in asymmetric synthesis. The development of chiral ligands with high specificity and efficiency was crucial for the advancement of asymmetric catalysis. Researchers sought to create ligands that could facilitate the formation of enantiomerically pure products, and (S)-(+)-DMPF was developed to address this need.

(S)-(+)-DMPF is synthesized through a multi-step process involving the reaction of ferrocenyl derivatives with phosphines and amines. The synthesis typically begins with the preparation of a ferrocenyl phosphine, which is then reacted with N,N-dimethyl-1-ethylamine. The resulting product is carefully purified to obtain (S)-(+)-DMPF in high enantiomeric purity. The synthesis of (S)-(+)-DMPF demonstrates the importance of precise chemical manipulation to achieve desired chiral properties.

One of the primary applications of (S)-(+)-DMPF is in asymmetric synthesis. As a chiral ligand, (S)-(+)-DMPF is employed in catalytic processes to produce enantiomerically pure compounds. Its ferrocenyl group imparts unique electronic and steric properties that enhance the selectivity and efficiency of the catalytic reactions. This property makes (S)-(+)-DMPF particularly valuable in the synthesis of pharmaceuticals and fine chemicals, where high enantiomeric purity is often required.

In addition to its role in asymmetric synthesis, (S)-(+)-DMPF is used in various catalytic reactions involving transition metals. Its ability to form stable complexes with metals such as palladium and rhodium contributes to its effectiveness as a ligand in these systems. These metal-ligand complexes facilitate a range of transformations, including cross-coupling reactions, hydrogenations, and other processes essential for organic synthesis.

The unique structure of (S)-(+)-DMPF, which combines a chiral amine with a ferrocenyl phosphine, provides significant advantages in designing catalytic systems with high specificity and reactivity. This design allows for the development of catalysts that can selectively promote desired reactions while minimizing side products. The use of (S)-(+)-DMPF in these applications highlights its importance in advancing the field of catalysis and organic synthesis.

The compound's stability and handling properties are well-suited for laboratory use. (S)-(+)-DMPF is generally handled with standard safety precautions, including proper storage and use of personal protective equipment. Its stability under various conditions makes it a reliable reagent for research and industrial applications.

Future research on (S)-(+)-DMPF may focus on expanding its applications in new catalytic systems and optimizing its performance in existing processes. The continued exploration of its properties and potential uses could lead to further innovations in asymmetric synthesis and catalytic chemistry.

References

1996. Asymmetric palladium-catalysed coupling reactions. Advanced Asymmetric Synthesis.
DOI: 10.1007/978-94-007-0797-9_14

1989. Enantioselective Catalysis with Metal Complexes. An Overview. Modern Synthetic Methods 1989.
DOI: 10.1007/978-3-642-83758-6_2