2-(t-Butyloxy)-ethylamine hydrochloride
[CAS# 335598-67-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: 2-(t-Butyloxy)-ethylamine hydrochloride
• Synonyms: 2-[(2-methylpropan-2-yl)oxy]ethanamine;hydrochloride
• Molecular Formula: C₆H₁₆ClNO
• Molecular Weight: 153.65
• CAS Registry Number: 335598-67-9
• SMILES: CC(C)(C)OCCN.Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

2‑(t‑Butyloxy)ethylamine hydrochloride is the hydrochloride salt of a tertiary amino ether. The compound features an ethylamine backbone modified with a bulky tert‑butoxy group. Its molecular formula is C₆H₁₅NO·HCl, and its molecular weight is approximately 153.7 g/mol. The structure combines a primary amine with a sterically demanding tert‑butoxy substituent, which imparts unique physical and chemical properties to the molecule.

The compound is typically supplied as a crystalline white solid, stable under normal conditions and easily stored at refrigerated temperatures (around 2 °C to 8 °C). The hydrochloride form markedly enhances water solubility and crystallinity, facilitating handling and formulation compared to the free base, which may be more volatile and less stable.

2‑(t‑Butyloxy)ethylamine hydrochloride serves primarily as a **synthetic intermediate** in medicinal chemistry and industrial chemistry. Its dual functional groups—an amine and an ether—allow it to participate in diverse chemical transformations. The tert‑butoxy moiety acts as a protective group or structural modifier, making the molecule useful in multi-step syntheses where selective reactivity is required. Reported uses include intermediacy in the development of pharmaceuticals, agrochemicals, specialty polymers, and surfactants.

In peptide and amino acid chemistry, this compound functions as a **deprotecting agent** for Boc-protected amines, enabling the release of the free amine under controlled conditions. The steric bulk and lipophilicity of the tert‑butoxy group can also enhance the compound's stability and reduce unwanted side reactions.

Applications extend to **formulation science**, where the compound’s structure can improve solubility and chemical stability of active ingredients. Its inclusion in synthesis workflows, particularly those involving sensitive functional groups, underscores its value in the design of complex molecules and novel chemical entities.

Safety considerations align with standard practices for amine compounds. The hydrochloride form is corrosive and may cause irritation upon skin or eye contact, or if inhaled. Proper PPE (gloves, eye protection) and adequate ventilation are recommended during handling. It should be stored away from heat and incompatible substances.

In summary, 2‑(t‑Butyloxy)ethylamine hydrochloride is a versatile and stable amino ether salt used chiefly as a functional synthetic intermediate. The presence of both a primary amine and tert‑butyl ether grants it flexibility in chemical transformations, while the hydrochloride form ensures practical handling and formulation compatibility in laboratory and industrial settings.

References

2024. Substituted aminothiazoles as DGKzeta inhibitors for immune activation. US Patent, US-11964953-B2.
Priority Date: 2020-04-24; Grant Date: 2024-04-23
URL: https://patents.google.com/patent/US11964953B2

2023. Substituted aminothiazoles as DGKzeta inhibitors for immune activation. US Patent Application, US-2023167078-A1.
Priority Date: 2020-04-24
URL: https://patents.google.com/patent/US2023167078A1

2023. Substituted aminothiazoles as DGKzeta inhibitors for immune activation. European Patent Application, EP-4139286-A1.
Priority Date: 2020-04-24
URL: https://patents.google.com/patent/EP4139286A1