1. Product Overview
(S)-(-)-1-Amino-2-propanol (CAS 1715-30-6), also known as (S)-(-)-2-aminopropan-1-ol or L-alaninol, is the chiral enantiomer of 1-amino-2-propanol with the (S) configuration at the α-carbon. With the molecular formula C₃H₉NO and a molecular weight of 75.11 g/mol, this chiral amino alcohol features both a primary amine (–NH₂) and a secondary alcohol (–OH) on adjacent carbon atoms, making it a versatile building block for asymmetric synthesis, chiral resolution, and pharmaceutical manufacturing. The (S) enantiomer is the natural L-alanine-derived configuration and is widely used as a chiral pool starting material for enantiomerically pure target molecules.
------
2. Key Features and Benefits
• Versatile Chiral Building Block: The adjacent amine and alcohol functional groups provide two orthogonal handles for stepwise derivatization—the NH₂ can be acylated/alkylated while preserving the OH, or vice versa.
• High Enantiomeric Purity: Supplied at ≥98% ee, ensuring clean stereochemical outcomes in asymmetric synthesis and chiral resolution processes.
• Natural L-Configuration: The (S) enantiomer corresponds to the L-alanine configuration, making it directly compatible with amino acid-based synthesis and peptide chemistry.
• Water-Miscible Liquid: Unlike many chiral auxiliaries that require organic solvents, (S)-alaninol is fully miscible with water and most organic solvents, simplifying reaction setup and workup.
• Commercially Established: Produced at scale via chiral resolution of racemic 1-amino-2-propanol or asymmetric reduction of amino ketones; >5000 kg/year global production capacity.
------
3. Major Applications
• Pharmaceutical Intermediate: Key building block for synthesizing chiral APIs including β-blockers (e.g., propranolol analogs), ACE inhibitors, and antiviral agents (e.g., oseltamivir precursors).
• Chiral Resolution Agent: Used to resolve racemic acids (e.g., ibuprofen, naproxen) via diastereomeric salt formation with the chiral amine, followed by fractional crystallization.
• Asymmetric Synthesis: Employed as a chiral ligand or auxiliary in enantioselective reactions including reductions (CBS-type), alkylations, and cycloadditions.
• Peptide & Amino Acid Chemistry: Serves as a chiral amine component in peptide coupling reactions, β-amino alcohol synthesis, and N-heterocycle construction (e.g., oxazolidines, morpholines).
• Agrochemical R&D: Used in the synthesis of chiral pesticides and herbicides where the (S)-alaninol scaffold contributes to selective toxicity and environmental safety.
• Catalyst & Ligand Design: Incorporated into chiral phosphine ligands, salen-type ligands, and organocatalysts for asymmetric hydrogenation and C–C bond formation.
• Academic Research: Studied in methodology development for enantioselective transformations, dynamic kinetic resolution, and flow chemistry applications.
------
4. Technical Specifications
Item Description
Product Name (S)-(-)-1-Amino-2-propanol (L-Alaninol)
Synonyms (S)-(-)-2-Aminopropan-1-ol; L-Alaninol; (S)-(-)-1-Aminopropan-2-ol; (2S)-2-Aminopropan-1-ol
CAS Number 1715-30-6
Molecular Formula C₃H₉NO
Molecular Weight 75.11 g/mol
MDL Number MFCD00064271
PubChem CID 442801
Assay (Purity) ≥95% / ≥98% (GC)
Enantiomeric Purity ≥98% ee
Optical Rotation [α]D²⁰ ≈ -18° to -22° (c = 1, H₂O) (Literature)
Appearance Colorless to pale yellow liquid (room temperature)
Boiling Point 159–161 °C (Literature)
Density 0.942–0.952 g/cm³ at 20 °C (Literature)
Refractive Index n²⁰/D ≈ 1.447–1.451 (Literature)
Flash Point ~67 °C (Predicted)
pKa (Predicted) ~9.5 ± 0.3 (NH₃⁺); ~15.5 ± 0.5 (OH)
Calculated LogP ~-0.8 to -0.5 (polar, water-miscible)
Polar Surface Area (PSA) 46.3 Ų
Hydrogen Bond Donors 3 (NH₂ + OH)
Hydrogen Bond Acceptors 2 (N + O)
Rotatable Bonds 1
Solubility Fully Miscible: Water, Methanol, Ethanol, DMSO, DMF, Acetone, THF, DCM, Chloroform, Hexane, Ether.
Spectral Data (Literature) ¹H NMR (CDCl₃, 400 MHz): δ 1.15 (d, J≈6.5 Hz, 3H, CH₃), 2.55 (br s, 2H, NH₂), 2.85–3.05 (m, 1H, CH-NH₂), 3.40 (dd, J≈11.0, 4.0 Hz, 1H, CH₂OH), 3.65 (dd, J≈11.0, 6.0 Hz, 1H, CH₂OH), 4.10 (br s, 1H, OH).
¹³C NMR (CDCl₃):δ 20.0 (CH₃), 48.0 (CH-NH₂), 65.0 (CH₂OH).
SMILES CC@@H(CO)N
InChI Key WGQWUSNSNOXEIG-SSDOTTSWSA-N
Storage (Liquid) 2–8 °C or room temperature, sealed, protected from air (N₂/Ar); stable ≥12–18 months
Sensitivity Air-sensitive (amine oxidizes slowly); hygroscopic; store under inert atmosphere
HS Code 2922.19.90 / 2933.99.90
------
5. Storage and Handling
• Storage: Store in a tightly sealed container at 2–8 °C (or room temperature for short-term), under an inert atmosphere (N₂ or Ar), protected from moisture. The primary amine is susceptible to aerial oxidation and CO₂ absorption; the container should be purged with N₂/Ar after each use. Stable for ≥12–18 months under proper conditions.
• Handling: Allow sealed container to warm to room temperature before opening to prevent condensation. Handle quickly in a fume hood with minimal air exposure. The compound is a low-viscosity liquid—use pipettes or syringes for accurate measurement.
• Solution Preparation: Readily miscible with water and all common organic solvents. For anhydrous reactions, dry over molecular sieves (3Å or 4Å) before use.
• Reactivity: The NH₂ group can be acylated (acid chlorides, anhydrides), alkylated (alkyl halides, Michael acceptors), or condensed (aldehydes, ketones). The OH group can be tosylated, mesylated, or oxidized to aldehyde/acid. The two groups can be cyclized to form oxazolidines with aldehydes.
• CO₂ Absorption: Amines absorb atmospheric CO₂ to form carbamates—this appears as a white precipitate in aged material. Remove by distillation or passing through a short column (SiO₂, elute with MeOH/NH₄OH).
------
6. Safety Summary (Full SDS Highlights)
• GHS Classification: GHS05 (Corrosive) + GHS07 (Warning)
• Signal Word: Warning
• Hazard Statements:
• H302: Harmful if swallowed.
• H312: Harmful in contact with skin.
• H315: Causes skin irritation.
• H319: Causes serious eye irritation.
• H335: May cause respiratory irritation.
• H412: Harmful to aquatic life with long lasting effects.
• Precautionary Statements:
• P261: Avoid breathing vapor/mist. Use only in a well-ventilated area or fume hood.
• P264: Wash hands, forearms, and face thoroughly after handling.
• P270: Do not eat, drink, or smoke in areas where this material is used.
• P271: Use only outdoors or in a well-ventilated area.
• P280: Wear protective gloves (nitrile), safety glasses with side shields, and lab coat.
• P301+P312: IF SWALLOWED: Call a POISON CENTER or physician if you feel unwell.
• P302+P352: IF ON SKIN: Wash with plenty of soap and water.
• P304+P340: IF INHALED: Remove person to fresh air and keep comfortable for breathing.
• P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
• P330: Rinse mouth if swallowed.
• P337+P313: If eye irritation persists: Get medical advice/attention.
• P403+P233: Store in a well-ventilated place. Keep container tightly closed.
• P501: Dispose of contents/container in accordance with local, regional, and national regulations.
• First Aid Measures:
• Inhalation: Remove to fresh air. If breathing difficult, administer oxygen and seek medical attention.
• Skin Contact: Immediately wash with plenty of soap and water. Remove contaminated clothing. Seek medical advice if irritation or rash develops.
• Eye Contact: Flush immediately with copious lukewarm water for at least 15 minutes. Remove contact lenses if possible. Seek medical attention.
• Ingestion: Rinse mouth. Do NOT induce vomiting. Give water to drink if conscious. Seek medical advice.
• Fire-Fighting Measures:
• Suitable Extinguishing Media: Water spray, alcohol-resistant foam, dry chemical, or CO₂.
• Special Hazards: Combustion may produce irritating/acrid smoke (CO, NOₓ). Nitrogen oxides are toxic.
• Protective Equipment: Wear self-contained breathing apparatus (SCBA) and full protective clothing.
• Spill Response:
• Absorb with inert material (sand, vermiculite). Do NOT use combustible materials. Prevent runoff from entering waterways or drains. Ventilate area after cleanup.
• Handling & Storage:
• Handle in fume hood. Keep container closed when not in use. Store at 2–8 °C (or room temperature), protected from moisture, under N₂/Ar. Keep away from strong oxidizers and strong acids.
• Hazardous Decomposition Products: Nitrogen oxides (NOₓ), carbon monoxide (CO), carbon dioxide (CO₂).
• Intended Use: For laboratory research and development ONLY. Not for human or veterinary therapeutic, diagnostic, or food use without appropriate regulatory approval. Handle as a hazardous amine.
