(S)-N,N-Dimethyl-1-ferrocenylethylamine (L)-tartrate
[CAS# 111614-65-4]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic iron
• Name: (S)-N,N-Dimethyl-1-ferrocenylethylamine (L)-tartrate
• Molecular Formula: C₁₈H₁₆FeNO₆
• Molecular Weight: 398.17
• CAS Registry Number: 111614-65-4
• EC Number: 695-682-5
• SMILES: CN([C@H]([C-]12C3=C4[Fe+2]5678923(C1=C45)[C-]1C6=C8C9=C71)C)C.OC(=O)[C@@H]([C@H](C(=O)O)O)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H331
Flammable liquids	Flam. Liq.	2	H225
Specific target organ toxicity - single exposure	STOT SE	1	H370
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H311

Discovery and Applications

(S)-N,N-Dimethyl-1-ferrocenylethylamine (L)-tartrate is a chiral organometallic compound that has garnered attention for its unique structure and versatile applications, particularly in asymmetric synthesis. The compound consists of a ferrocenyl group attached to an ethylamine moiety, which is further modified with N,N-dimethylation. The chirality is introduced through the (S)-configuration of the ferrocenylethylamine, and it is paired with (L)-tartrate, a naturally occurring chiral acid, to form a stable salt.

The discovery of (S)-N,N-Dimethyl-1-ferrocenylethylamine (L)-tartrate was driven by the need for efficient chiral auxiliaries and ligands in asymmetric catalysis. The ferrocenyl group, known for its stability and redox properties, serves as an excellent scaffold for creating chiral environments. The combination of this ferrocenyl group with the (L)-tartrate provides a robust chiral structure that can be utilized in various enantioselective processes.

One of the primary applications of (S)-N,N-Dimethyl-1-ferrocenylethylamine (L)-tartrate is in the resolution of racemic mixtures, where it is used as a resolving agent to separate enantiomers. Its ability to form diastereomeric salts with racemic compounds allows for the selective crystallization of one enantiomer, facilitating the production of optically pure substances. This property is especially valuable in the pharmaceutical industry, where the chirality of drug molecules often determines their efficacy and safety.

Additionally, this compound has found use as a chiral ligand in asymmetric catalysis. In particular, it has been employed in catalytic asymmetric hydrogenation and other enantioselective reactions. The presence of the ferrocenyl group enhances the stability and reactivity of the catalyst, while the chiral environment provided by the (S)-N,N-dimethyl-1-ferrocenylethylamine ensures high enantioselectivity in the formation of chiral products.

In summary, (S)-N,N-Dimethyl-1-ferrocenylethylamine (L)-tartrate is a valuable chiral compound with significant applications in asymmetric synthesis and chiral resolution. Its unique structure, combining a ferrocenyl group with a chiral amine and (L)-tartrate, makes it a versatile tool in the production of optically pure compounds, which are essential in various chemical industries.

References

none