2-(tert-Butylthio)ethanamine: Properties, Uses & Handling FAQ

2-(tert-Butylthio)ethanamine is a bifunctional organic building block bearing both a primary amine and a sterically hindered tert-butyl thioether group, making it a versatile reagent for medicinal chemistry, peptide modification, and heterocyclic synthesis.

Chemical Name

2-(tert-Butylthio)ethanamine

SKU

t168763

Molecular Formula

C6H15NS

Molecular Weight

133.26 g/mol

Functional Groups

Primary amine (–NH2) and tert-butyl thioether (–S–C(CH3)3)

Appearance

Colorless to pale yellow liquid

Recommended Storage

Store at 2–8 °C under inert atmosphere, away from oxidizing agents

Chemical Identity and Structure

2-(tert-Butylthio)ethanamine (SKU t168763) has the molecular formula C₆H₁₅NS and a molecular weight of approximately 133.26 g/mol. Its IUPAC name reflects two key structural features: a two-carbon ethylamine backbone bearing a primary amino group (–NH₂) at one terminus and a tert-butyl sulfide (–S–C(CH₃)₃) at the other. The tert-butyl group imparts significant steric bulk around the sulfur atom, which influences both the reactivity and selectivity of the molecule in synthetic transformations. The compound is classified as a thioether-amine, belonging to the broader family of sulfur-containing aliphatic amines used as bifunctional building blocks in organic and medicinal chemistry.

Applications in Research and Synthesis

The dual functionality of 2-(tert-Butylthio)ethanamine makes it a valuable intermediate in multiple research contexts. The primary amine group readily participates in acylation, reductive amination, sulfonamide formation, and Schiff base condensation reactions, while the thioether moiety can serve as a latent thiol precursor upon deprotection of the tert-butyl group under acidic conditions. This allows chemists to introduce a free thiol at a controlled synthetic stage, which is particularly useful in the preparation of cysteine analogs, thiol-containing linkers for bioconjugation, and peptidomimetic scaffolds. Additionally, the compound finds use as a building block for the synthesis of heterocyclic compounds, coordination ligands, and pharmacophore fragments in drug discovery programs.

Storage, Handling and Safety

2-(tert-Butylthio)ethanamine should be stored at 2–8 °C in a tightly sealed container under an inert atmosphere (nitrogen or argon) to prevent oxidation of the thioether and potential amine degradation. As with most low-molecular-weight aliphatic amines, the compound may have a characteristic odor and should be handled in a well-ventilated fume hood. Appropriate personal protective equipment (PPE) including chemical-resistant gloves, safety goggles, and a lab coat is required. Contact with skin, eyes, and mucous membranes should be avoided. The compound should be kept away from strong oxidizing agents and strong acids. Consult the Safety Data Sheet (SDS) provided with the product before use, as it contains specific hazard classifications, first-aid measures, and disposal guidance.

Purity, Quality and Regulatory Information

Aladdin Scientific supplies 2-(tert-Butylthio)ethanamine (t168763) as a research-grade reagent. Purity specifications and analytical data, including NMR and GC purity, are provided on the product certificate of analysis (CoA) available upon request or via the Aladdin website. Researchers should verify the CoA for each lot before use, particularly for sensitive applications such as asymmetric synthesis or biological assays. The compound is intended for research and development purposes only and is not suitable for use in clinical, diagnostic, or food applications without further validation. Customers are advised to check applicable local regulations regarding the import, storage, and use of sulfur-containing amine reagents.

Ordering and Technical Support

2-(tert-Butylthio)ethanamine is available from Aladdin Scientific under SKU t168763. Orders can be placed through the Aladdin website, by contacting your regional sales representative, or via established procurement channels. For bulk quantity inquiries, custom packaging, or specific purity grades, please reach out to Aladdin's sales team directly. Technical questions regarding the compound's reactivity, compatibility with specific synthetic protocols, or application troubleshooting can be directed to Aladdin's technical support team. Standard lead times and shipping conditions apply; please consult the shipping and delivery information on the Aladdin website for cold-chain requirements relevant to this product.

Frequently asked questions

What is the molecular formula and molecular weight of 2-(tert-Butylthio)ethanamine?

2-(tert-Butylthio)ethanamine has the molecular formula C6H15NS and a molecular weight of approximately 133.26 g/mol. It contains both a primary amine and a tert-butyl thioether functional group.

What is the tert-butylthio group used for in organic synthesis?

The tert-butylthio group functions as an S-tert-butyl protected thiol. Under acidic deprotection conditions, it can be removed to reveal a free thiol (–SH), enabling sequential synthetic strategies where thiol introduction is needed at a later stage. This is especially useful in bioconjugation, peptide synthesis, and preparation of cysteine analogs.

How should 2-(tert-Butylthio)ethanamine be stored to maintain stability?

The compound should be stored at 2–8 °C in a tightly sealed container under an inert atmosphere such as nitrogen or argon. It should be kept away from strong oxidizing agents and strong acids, which could degrade either the thioether or the amine functionality.

Is 2-(tert-Butylthio)ethanamine suitable for biological or clinical applications?

No. The compound is supplied as a research-grade reagent intended solely for research and development purposes. It is not validated for clinical, diagnostic, therapeutic, or food applications. Researchers should review the product CoA and SDS before use in any biological assay.

Can the primary amine group of 2-(tert-Butylthio)ethanamine participate in standard amine coupling reactions?

Yes. The primary amine group is reactive and can participate in a variety of standard transformations including acylation with activated esters or acid chlorides, reductive amination with aldehydes or ketones, sulfonamide formation, and condensation with carbonyl compounds to form imines. Chemists should optimize reaction conditions to preserve the thioether group during such transformations.

Where can I find the Certificate of Analysis (CoA) for SKU t168763?

The Certificate of Analysis for 2-(tert-Butylthio)ethanamine (t168763) can be accessed through the Aladdin Scientific website by searching the SKU or by contacting Aladdin's customer service team. Lot-specific CoA documents are recommended to verify purity and analytical data before use.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley: New York, 1992. (General reference for amine and thioether chemistry.)
2. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 4th ed.; Wiley: Hoboken, NJ, 2006. (Reference for S-tert-butyl thiol protection strategy.)
3. Aladdin Scientific product page for 2-(tert-Butylthio)ethanamine, SKU t168763. Aladdin Scientific Corp.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.