2-(Methoxymethoxy)-N,N-bis[2-(methoxymethoxy)ethyl]ethan-1-amine
[CAS 211919-60-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: 2-(Methoxymethoxy)-N,N-bis[2-(methoxymethoxy)ethyl]ethan-1-amine
• Molecular Formula: C₁₂H₂₇NO₆
• Molecular Weight: 281.35
• CAS Registry Number: 211919-60-7
• SMILES: COCOCCN(CCOCOC)CCOCOC

Discovery and Applications

2-(Methoxymethoxy)-N,N-bis[2-(methoxymethoxy)ethyl]ethan-1-amine is a multifunctional tertiary amine characterized by the presence of multiple **methoxymethyl (MOM) ether** groups. Its structure consists of a central tertiary amine nitrogen bonded to three alkyl chains, each bearing a methoxymethoxy substituent. This combination makes the molecule both highly polar and capable of acting as a ligand or protecting-group-containing intermediate in organic synthesis.

The molecular structure features a tertiary amine core, N(CH₂CH₂–OMOM)₂–CH₂–OMOM (where OMOM represents –O–CH₂–O–CH₃). The methoxymethyl groups are commonly used as protecting groups for alcohols, and their presence in this molecule imparts flexibility, electron-donating character through oxygen atoms, and increased solubility in organic solvents. The tertiary amine can be protonated under acidic conditions, forming water-soluble salts, or can coordinate to metal centers as a neutral ligand.

Synthesis of this compound typically involves alkylation of a primary amine (such as ethanolamine derivatives) with methoxymethyl-protected haloalkanes. Alternatively, stepwise introduction of methoxymethyl groups onto hydroxyethyl-substituted amines can be employed, ensuring that the protecting groups remain intact under controlled reaction conditions.

This compound is mainly used as an intermediate or auxiliary in organic synthesis. The methoxymethyl groups can serve as removable protecting groups, allowing selective deprotection under acidic conditions to reveal hydroxyl functionalities. The tertiary amine functionality can also participate in base-catalyzed reactions, phase-transfer processes, or coordination chemistry.

In addition, molecules of this type may be used as ligands in coordination chemistry, where the nitrogen and oxygen atoms can interact with metal ions, forming chelates or complexes. Their flexible, multidentate nature can be useful in stabilizing metal centers or tuning catalytic activity.

Overall, 2-(methoxymethoxy)-N,N-bis[2-(methoxymethoxy)ethyl]ethan-1-amine is a structurally flexible, multifunctional tertiary amine bearing multiple MOM ether groups. Its combination of protecting-group functionality, coordination ability, and solubility properties makes it a useful intermediate in synthetic organic chemistry and materials-related applications.

References

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