Chemical Identity and Structural Features

Ethyl 3-amino-3-(pyridin-3-yl)propanoate dihydrochloride is a beta-amino ester in which the alpha-carbon carries a free primary amine and the beta-carbon bears an ethyl ester group. The pyridin-3-yl (nicotinyl) ring attached at the 3-position introduces a basic nitrogen into the aromatic framework, conferring metal-chelating capability and influencing the compound's physicochemical properties such as solubility and pKa.

Presentation as the dihydrochloride salt substantially improves bench stability and aqueous solubility compared with the free base form, making it easier to weigh accurately and dissolve for reaction setup. The two protonation sites correspond to the aliphatic amine and the pyridine nitrogen. Researchers should account for both equivalents of HCl when calculating stoichiometry and when selecting base for neutralization prior to reaction.

Handling, Dissolution, and Storage Guidelines

Personal Protective Equipment: Handle in a well-ventilated fume hood. Wear appropriate PPE including nitrile gloves, safety glasses, and a lab coat. Consult the Safety Data Sheet (SDS) for full hazard information before use.

Dissolution: The dihydrochloride salt is freely soluble in water and polar protic solvents such as methanol and ethanol. For reactions requiring an anhydrous medium, dimethyl sulfoxide (DMSO) or dimethylformamide (DMF) may be used. When the free-base form is required, treat an aqueous solution with a mild base (e.g., sodium bicarbonate or triethylamine) and extract into an appropriate organic solvent, or use an ion-exchange resin protocol.

Stoichiometric Note: Because the compound is supplied as the dihydrochloride salt, the molecular weight used for weighing must reflect both HCl equivalents. Always verify the exact molecular weight from the Certificate of Analysis (CoA) provided with each lot.

Storage: Store tightly sealed in a cool, dry location, protected from light and atmospheric moisture. Refer to the product label and SDS for lot-specific storage temperature recommendations. Prolonged exposure to humidity may cause caking without significant loss of chemical integrity, but accurate weighing will be compromised.

Applications in Synthetic and Medicinal Chemistry

Amide Bond Formation: The free primary amine, once liberated from the salt or neutralized in situ, reacts efficiently with activated carboxylic acids, acyl chlorides, or N-hydroxysuccinimide (NHS) esters to yield beta-amino amide products. These motifs are common in peptidomimetic drug candidates and protease inhibitor scaffolds.

Reductive Amination: The amine group participates in reductive amination reactions with aldehydes and ketones in the presence of reducing agents such as sodium cyanoborohydride or sodium triacetoxyborohydride, enabling rapid diversification of the nitrogen substituent.

Ester Hydrolysis and Further Functionalization: The ethyl ester can be hydrolyzed under mild basic or acidic conditions to afford the corresponding beta-amino acid, which may then be incorporated into peptide chains or cyclized to form beta-lactam or diketopiperazine ring systems.

Heterocyclic Synthesis: The combination of a proximal amine and ester functionality, together with the pyridyl ring, makes this compound a useful precursor for constructing fused bicyclic and polycyclic heterocyclic frameworks relevant to kinase inhibitor and GPCR ligand programs.

Quality, Purity, and Analytical Verification

Each lot of Ethyl 3-amino-3-(pyridin-3-yl)propanoate dihydrochloride from Aladdin Scientific is accompanied by a Certificate of Analysis (CoA) specifying lot-specific purity data. Researchers should request and review the CoA upon receipt to verify that the compound meets the minimum purity threshold required for their application.

Recommended Analytical Methods:

• HPLC: Reverse-phase HPLC (C18 column, UV detection at 254 nm or 270 nm) is the standard method for purity assessment of this compound.
• NMR Spectroscopy: ¹H and ¹³C NMR in D₂O or CD₃OD confirm structural identity and reveal the protonation state. The pyridyl ring protons appear as characteristic multiplets in the 8.5–9.0 ppm region.
• Mass Spectrometry: ESI-MS provides confirmation of the molecular ion corresponding to the free base; m/z assignment should match the expected formula.
• Karl Fischer Titration: Recommended if moisture content is critical for stoichiometric accuracy in your application.

If analytical data indicate degradation (e.g., new HPLC peaks, discoloration), the compound should be discarded and a fresh lot ordered.

Regulatory and Safety Considerations

Ethyl 3-amino-3-(pyridin-3-yl)propanoate dihydrochloride is intended for research use only and is not approved for human therapeutic, veterinary, food, agricultural, or household use. Users are responsible for compliance with all applicable local, national, and international regulations governing the purchase, handling, storage, and disposal of research chemicals.

Waste Disposal: Dispose of residues and solutions in accordance with institutional guidelines and applicable environmental regulations. Do not pour chemical waste down the drain without authorization from your institutional Environmental Health and Safety (EHS) office.

Export Control: Buyers are responsible for confirming that the import and use of this compound complies with all relevant export control and customs regulations in their jurisdiction.

Always consult the current SDS before initiating work with this compound. The SDS is available for download from the Aladdin Scientific product page for SKU E191049.