2-Amino-1,3-propanediol (Serinol) 534-03-2 98% White to Off-White Crystalline Powder Chiral Amino Diol / Pharmaceutical Intermediate

1. Product Overview

2-Amino-1,3-propanediol (CAS 534-03-2), also known as Serinol or (R/S)-2-aminopropane-1,3-diol, is a symmetrical β-amino diol with the molecular formula C₃H₉NO₂ and a molecular weight of 91.11 g/mol. It is the reduced form of serine and a valuable chiral/achiral building block bearing both a primary amine and two primary hydroxyl groups. This compound is widely used as a pharmaceutical intermediate—most notably in the synthesis of non-ionic X-ray contrast media (e.g., iopamidol, iohexol precursors) and as a scaffold for β-lactam, antiviral, and peptidomimetic syntheses via selective protection/deprotection of the OH/NH₂ groups.

2. Key Features and Benefits

• Symmetric β-Amino Diol: Two primary –OH groups and a primary –NH₂ provide three orthogonal handles for stepwise derivatization (acylation, alkylation, tosylation).

• Pharmaceutical Intermediate: Key starting material for the side-chain of non-ionic iodinated contrast agents and for chiral auxiliaries in asymmetric synthesis.

• Water-Miscible & Hygroscopic: Freely soluble in water and polar organic solvents; convenient for aqueous-phase reactions.

• High Purity: Supplied at ≥95% or ≥98% (GC/Titration), suitable for multi-step pharmaceutical synthesis.

• Stable Crystalline Form: White to off-white solid, stores well under recommended conditions.

3. Major Applications

• Pharmaceutical Intermediate: Used in the synthesis of iodinated X-ray contrast media (iopamidol, iohexol type) and as a precursor to chiral ligands, β-lactams, and nucleoside analogs.

• Asymmetric Synthesis / Chiral Auxiliary: N- or O-functionalized to generate chiral catalysts or templates for enantioselective alkylation and acylation.

• Polymer & Material Science: Incorporated as a diol monomer in polyester or polyurethane synthesis; used in surfactant design after selective derivatization.

• Organic Synthesis: Employed in the preparation of oxazolidines, morpholines, and other N,O-heterocycles via cyclocondensation.

• Analytical Reference: Serves as a standard for amino diol quantification in process chemistry and quality control.

4. Technical Specifications

Item Description
Product Name 2-Amino-1,3-propanediol (Serinol)
Synonyms Serinol; 2-Aminopropane-1,3-diol; (±)-2-Amino-1,3-propanediol
CAS Number 534-03-2
Molecular Formula C₃H₉NO₂
Molecular Weight 91.11 g/mol
MDL Number MFCD00004549
PubChem CID 11257
Assay (Purity) ≥95% / ≥98% (GC / Titration)
Appearance White to off-white crystalline powder or flakes
Melting Point 52–55 °C (Literature)
Boiling Point ~277 °C
Density ~1.18 g/cm³
pKa (Predicted) ~9.5 ± 0.3 (NH₃⁺); ~14.5 ± 0.5 (OH)
Calculated LogP ~-1.5 to -1.0 (polar, zwitterionic in water)
Polar Surface Area (PSA) 66.5 Ų
Hydrogen Bond Donors 3 (NH₂ + 2×OH)
Hydrogen Bond Acceptors 3 (N + 2×O)
Rotatable Bonds 2
Solubility Very Soluble: Water (>100 mg/mL), Methanol, Ethanol.
Slightly Soluble:Acetone, Isopropanol.
Insoluble:Ether, Hexane, Toluene.
Spectral Data (Literature) ¹H NMR (D₂O, 400 MHz): δ 2.80 (t, J≈5.5 Hz, 2H, CH₂-NH₃⁺), 3.65 (t, J≈5.5 Hz, 2H, CH₂-OH ×2), 4.10 (br s, 3H, OH + NH₃⁺).
¹³C NMR (D₂O):δ 42.0 (CH₂-N), 62.5 (CH₂-OH ×2).
SMILES NCC(CO)O
InChI Key CSCPPACGZOOCGX-UHFFFAOYSA-N
Storage (Powder) 2–8 °C, sealed, protected from light & moisture; highly hygroscopic—store in desiccator
HS Code 2922.19.90 / 3822.90.00

5. Storage and Handling

• Storage: Store in a tightly sealed container at 2–8 °C, protected from moisture (desiccator recommended). The compound is strongly hygroscopic and will absorb atmospheric water—weigh quickly after opening. Stable for ≥18–24 months.

• Handling: Allow sealed vial to warm to room temperature before opening to prevent condensation. Dissolve in water, MeOH, or EtOH. Minimize exposure time to air.

• Solution Preparation: Highly soluble in water (up to ~5 M). For anhydrous reactions, dry over molecular sieves (3Å or 4Å) before use. Can be protected as N-Cbz or N-Boc derivative; OH groups protected as tosylates or silyl ethers.

• Freeze-Thaw: Aqueous stocks stable at 4 °C for several weeks; for long-term, aliquot and freeze at -20 °C. Avoid repeated freeze-thaw.

6. Safety Summary (SDS Highlights)

• GHS Classification: GHS05 (Corrosive) + GHS07 (Warning)

• Signal Word: Danger

• Hazard Statements: H314 (Causes severe skin burns and eye damage), H335 (May cause respiratory irritation)

• Precautionary Statements: P260, P264, P271, P280 (wear face shield + nitrile gloves), P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P405, P501

• First Aid: Skin—flush with water ≥15 min; Eye—irrigate ≥15 min, seek medical attention; Ingestion—rinse mouth, do NOT induce vomiting, seek medical advice.

• Fire-Fighting / Spill: Water spray, alcohol-resistant foam, dry chemical, or CO₂. Sweep up in inert absorbent; prevent entry to drains.

• Intended Use: For laboratory research and development ONLY. Not for human or veterinary therapeutic, diagnostic, or food use.

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