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2-(2-Methoxyphenoxy)ethylamine is an organic amine featuring a two-carbon ethyl chain with a primary amine (-NH₂) at one end and a phenoxy group (aromatic ether) at the other. The phenyl ring bears a methoxy (-OCH₃) group at the ortho position (adjacent to the ether oxygen). This structure combines amine reactivity with aromatic stability, making it useful in pharmaceutical synthesis (e.g., beta-blocker intermediates) and organic chemistry. It is typically a basic liquid/solid with limited water solubility, often forming salts with acids. Synthesis involves ether-forming reactions (e.g., Williamson) between 2-methoxyphenol and amine-containing precursors. Handle with care due to potential skin/eye irritation.
2-(2-Methoxyphenoxy)ethylamine is an organic compound with the following structure and characteristics:
Backbone: Ethylamine (CH₂CH₂NH₂), where the amine group (-NH₂) is attached to the first carbon of a two-carbon chain.
Substituent: A phenoxy group (O-C₆H₄) is attached to the second carbon of the ethyl chain.
Phenoxy Group Modification: The phenyl ring of the phenoxy group has a methoxy group (-OCH₃) at the ortho position (carbon 2 relative to the oxygen connecting to the ethyl chain).
Structural Formula:
NH₂-CH₂-CH₂-O-C₆H₃(2-OCH₃)
Functional Groups:
Primary amine (-NH₂).
Ether linkages (phenoxy and methoxy groups).
Physical Properties:
Likely a liquid or low-melting solid at room temperature.
Basic due to the amine group, capable of forming salts with acids.
Moderate solubility in organic solvents; limited water solubility unless protonated.
Synthesis:
Nucleophilic substitution: Reacting 2-methoxyphenol with a bromoethylamine derivative.
Williamson ether synthesis: Using 2-methoxyphenoxide and a tosylated ethanolamine.
Gabriel synthesis: Converting 2-(2-methoxyphenoxy)ethanol to an amine via intermediate steps.
Possible routes include:
Applications:
Pharmaceutical Intermediate: Similar structures are found in beta-blockers or other amine-based drugs.
Organic Synthesis: Building block for ligands, polymers, or bioactive molecules.
Safety:
Typical amine hazards: Irritant to skin/eyes. Requires standard lab precautions (gloves, goggles).
This compound is a functionalized ethylamine with aromatic ether groups, notable for its potential use in medicinal chemistry and organic synthesis. Its structure combines reactivity from the amine group with the stability of methoxy-substituted aromatic rings.
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