What Is N-Boc-DL-2-amino-1-propanol?

N-Boc-DL-2-amino-1-propanol is the tert-butoxycarbonyl (Boc) protected form of DL-2-amino-1-propanol (DL-alaninol). It bears two key functional groups: a Boc-protected secondary amine at the 2-position and a free primary hydroxyl group at the 1-position. Because the compound is the racemic (DL) form, it contains equal amounts of the R and S enantiomers, making it cost-effective for applications where stereochemistry at this center is not critical or where subsequent resolution steps are planned.

The Boc group provides orthogonal, acid-labile protection of the amine, allowing selective manipulation of the hydroxyl group under basic or neutral conditions. This orthogonality makes it a highly practical intermediate in multi-step synthesis workflows.

Physicochemical Properties and Storage

N-Boc-DL-2-amino-1-propanol typically presents as a white to off-white crystalline solid at room temperature. Key physicochemical data are summarized in the Key Facts section above. The compound is soluble in common organic solvents including dichloromethane, tetrahydrofuran, ethyl acetate, methanol, and dimethylformamide.

For long-term storage, keep the compound in a tightly sealed container under cool, dry conditions (2–8 °C is recommended) and protect from moisture. The Boc protecting group is stable under these conditions but can be cleaved by strong acids such as trifluoroacetic acid (TFA) or hydrochloric acid in dioxane, which is precisely the basis for its utility as a protecting group. Exposure to strong acids or prolonged heating should therefore be avoided during storage and general handling.

Applications in Organic and Medicinal Chemistry

N-Boc-DL-2-amino-1-propanol is widely employed as a bifunctional building block in the synthesis of pharmaceuticals, natural product analogs, and specialty materials. Its two differentially protected functional groups—a free hydroxyl and a Boc-masked amine—allow sequential, chemoselective transformations such as:

• Hydroxyl activation: Conversion to mesylate, tosylate, or halide intermediates for subsequent nucleophilic substitution.
• Amine deprotection and functionalization: Removal of the Boc group with TFA or HCl to reveal the free amine, followed by acylation, sulfonylation, or reductive amination.
• Cyclization reactions: Formation of morpholine, oxazolidinone, or other heterocyclic scaffolds relevant to drug discovery.
• Peptide and peptidomimetic synthesis: Incorporation as a beta-amino alcohol component.

The racemic nature of the compound is suitable for early-stage library synthesis or screening, while enantiopure derivatives can be accessed via chiral resolution or by using the corresponding L- or D-alaninol Boc derivatives.

Handling, Safety and Regulatory Notes

As with most amine-containing reagents, standard laboratory precautions apply when handling N-Boc-DL-2-amino-1-propanol. Use appropriate personal protective equipment (PPE) including gloves, safety glasses, and a lab coat. Work in a well-ventilated area or fume hood. Avoid contact with eyes, skin, and clothing.

Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific (SKU: I131988) for specific hazard classifications, first-aid measures, disposal instructions, and transport information before use. This compound is intended for research use only and is not for human or veterinary therapeutic use.

Ordering and Specifications at Aladdin Scientific

N-Boc-DL-2-amino-1-propanol is available from Aladdin Scientific under SKU I131988. When placing an order, researchers and procurement teams should confirm the required pack size, purity grade, and certificate of analysis (CoA) requirements. Standard purity specifications and analytical data (including HPLC, NMR) are typically available upon request or downloadable from the product page.

For bulk quantities, custom purity grades, or questions about availability, please contact Aladdin Scientific's technical support or sales team directly. Volume pricing and institutional purchase agreements may be available for qualified accounts.