3-Ethoxy-4-methoxy-alpha-[(methylsulfonyl)methyl]-benzenemethanamine
[CAS# 253168-94-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: 3-Ethoxy-4-methoxy-alpha-[(methylsulfonyl)methyl]-benzenemethanamine
• Synonyms: 1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine
• Molecular Formula: C₁₂H₁₉NO₄S
• Molecular Weight: 273.35
• CAS Registry Number: 253168-94-4
• EC Number: 807-312-3
• SMILES: CCOC1=C(C=CC(=C1)C(CS(=O)(=O)C)N)OC

Properties

• Solubility: Slightly soluble (3.8 g/L) (25 °C), Calc.^*
• Density: 1.195±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.528, Calc.^*
• Boiling Point: 469.6±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 237.8±28.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302+H312+H332-H302-H312-H315-H319-H332
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

3-Ethoxy-4-methoxy-alpha-[(methylsulfonyl)methyl]-benzenemethanamine is a synthetic compound known for its versatility in organic and medicinal chemistry, primarily as a building block in the synthesis of pharmacologically active molecules. Its structure, characterized by an aromatic ring substituted with both ethoxy and methoxy groups and a benzenemethanamine core modified by a methylsulfonyl group, grants it unique reactivity and allows for controlled modifications that are beneficial in drug development.

The discovery and utilization of this compound stem from research on aromatic amines with sulfonyl substitutions, which showed potential as intermediates in synthesizing substances with bioactive properties. These findings spurred further exploration into derivatives of benzenemethanamine, leading to the development of 3-ethoxy-4-methoxy-alpha-[(methylsulfonyl)methyl]-benzenemethanamine. Its functional groups, particularly the ethoxy, methoxy, and methylsulfonyl moieties, enhance its reactivity, solubility, and stability, making it ideal for creating compounds that target specific biological pathways.

One of the key applications of this compound is in pharmaceutical research, where it is used as a scaffold for synthesizing drug candidates. Its structural framework enables the formation of analogs that can target enzymes, receptors, or specific cell signaling pathways, with particular relevance to neurological and inflammatory conditions. The methylsulfonyl group, in particular, imparts high bioavailability, aiding in the compound’s solubility and absorption across biological membranes. The compound’s reactivity profile also facilitates the design of selective inhibitors or modulators, allowing medicinal chemists to tune its pharmacokinetic and pharmacodynamic properties for therapeutic purposes.

In addition to its medicinal applications, 3-ethoxy-4-methoxy-alpha-[(methylsulfonyl)methyl]-benzenemethanamine is valuable in agrochemical research. It serves as a precursor in the synthesis of bioactive compounds that can act as insecticides or fungicides, leveraging its stability and reactivity to ensure efficient action in various environmental conditions. Its incorporation into chemical agents designed to disrupt pest and microbial activity highlights its versatility in synthetic organic chemistry.

References

2015. Apremilast. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-01-0207