(S)-3-Amino-3-phenylpropan-1-ol RC00259

Manufacturer: Hangzhou Royalchem Co.,LTD.

Website:   www.cnroyalchem.com

Here is a detailed product description for  (S)-3-Amino-3-phenylpropan-1-ol  (CAS # 82769-76-4):

1. Chemical Identity:  *  Product Name:  (S)-3-Amino-3-phenylpropan-1-ol *  Synonyms:  (S)-3-Amino-3-phenyl-1-propanol; (S)-3-Amino-1-phenylpropan-3-ol; (S)-3-Hydroxy-3-phenylpropylamine; (S)-3-Phenyl-3-aminopropanol; (S)-β-Amino-β-phenylpropanol *  CAS Registry Number:  82769-76-4 *  Molecular Formula:  C₉H₁₃NO *  Molecular Weight:  151.21 g/mol *  IUPAC Name:  (S)-3-Amino-3-phenylpropan-1-ol

2. Structural Features & Stereochemistry:  *  Core Structure:  Features a phenyl ring attached directly to a chiral center (C3). *  Functional Groups:  * Primary amine (-NH₂) attached to the chiral center (C3). * Primary alcohol (-CH₂OH) attached to C1. *  Chirality:  Possesses one stereogenic center (C3). The designation  (S)  indicates the specific absolute configuration around this carbon atom. This enantiomeric purity is crucial for its applications in asymmetric synthesis and chiral recognition. *  Relationship:  The enantiomerically pure counterpart to (R)-3-Amino-3-phenylpropan-1-ol (CAS 82769-75-3). Also structurally related to the racemic mixture (DL-3-Amino-3-phenylpropan-1-ol, CAS 2607-72-3).

3. Physical Properties (Typical):  *  Appearance:  White to off-white crystalline solid or powder. *  Melting Point:  Typically reported in the range of 65 °C to 75 °C (exact value can vary slightly between suppliers/purity grades). *  Solubility:  Generally soluble in common polar organic solvents (e.g., methanol, ethanol, acetone, dichloromethane, ethyl acetate). Moderately soluble in water. Low solubility in non-polar solvents (e.g., hexane, toluene). *  Optical Rotation:  Exhibits specific optical rotation due to its chirality. A representative value is approximately [α]²⁵D = -30° to -40° (c=1 in Methanol), but precise values depend on concentration, solvent, and purity/enantiomeric excess (ee). *  Boiling Point:  Not typically a primary specification due to decomposition risks; often decomposes upon heating under atmospheric pressure.

4. Chemical Properties:  *  Reactivity:  Contains two highly versatile functional groups: *  Primary Amine:  Acts as a nucleophile (e.g., forms amides, imines, enamines). Can be readily protected (e.g., as carbamates like Boc, Fmoc, or Cbz). *  Primary Alcohol:  Can undergo esterification, etherification, oxidation (to aldehyde/carboxylic acid), tosylation/mesylation, etc. *  Amphoterism:  Can act as both a base (amine group) and a weak acid (alcohol group) depending on conditions. *  Stability:  Generally stable when stored properly. Sensitive to strong oxidizing agents. May undergo racemization under harsh conditions (strong acid/base, high temperature). Air/moisture sensitivity is generally low, but storage under inert atmosphere is often recommended for long-term stability, especially to prevent potential salt formation or oxidation.

5. Key Specifications (Commercial Grades):  *  Purity:  Typically ≥97% or ≥98% (determined by GC, HPLC, or titration). *  Enantiomeric Excess (ee):  Crucial specification. Usually offered as ≥98% ee or ≥99% ee, confirmed by chiral HPLC or GC. This is the defining characteristic for its use in asymmetric synthesis. *  Melting Point:  Consistent with literature/supplier COA (e.g., 68-72°C). *  Optical Rotation:  Measured and reported on the COA.

6. Primary Applications & Uses:  *  Chiral Building Block:  Highly valuable synthon in the asymmetric synthesis of complex molecules, particularly pharmaceuticals and natural products. The chiral β-amino alcohol motif is a privileged structure. *  Ligand for Asymmetric Catalysis:  Serves as a precursor for designing chiral ligands (e.g., oxazaborolidines, amino-alcohol based ligands) used in enantioselective reactions (e.g., reduction, aldol, Diels-Alder). *  Pharmaceutical Intermediates:  Used in the synthesis of chiral drugs, especially those targeting the central nervous system (CNS), analgesics, or β-adrenergic receptor agents. Key intermediate for compounds like (R,S)-Fluoxetine precursors. *  Resolution Agent:  Can be used in the resolution of racemic acids via diastereomeric salt formation. *  Research & Development:  Fundamental compound in organic and medicinal chemistry research exploring new synthetic methodologies, chiral auxiliaries, and structure-activity relationships (SAR).

7. Handling, Storage & Safety:  *  Handling:  Handle with appropriate personal protective equipment (PPE: gloves, safety glasses, lab coat). Use in a well-ventilated area or fume hood. Avoid contact with skin, eyes, and clothing. Avoid breathing dust. Avoid generating dust aerosols. *  Storage:  Store tightly sealed in a cool (2-8°C recommended), dry place, protected from light and moisture. Storing under an inert atmosphere (Argon, Nitrogen) is often recommended for optimal long-term stability, especially for high-purity/ee material. *  Stability:  Stable under recommended storage conditions. Combustible solid. *  Hazard Statements (GHS - Typical):  *  H315:  Causes skin irritation. *  H319:  Causes serious eye irritation. *  H335:  May cause respiratory irritation. *  Precautionary Statements (P - Typical):  *  P261:  Avoid breathing dust/fume/gas/mist/vapours/spray. *  P264:  Wash hands thoroughly after handling. *  P271:  Use only outdoors or in a well-ventilated area. *  P280:  Wear protective gloves/protective clothing/eye protection/face protection. *  P302+P352:  IF ON SKIN: Wash with plenty of soap and water. *  P305+P351+P338:  IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. *  P312:  Call a POISON CENTER/doctor/... if you feel unwell. *  P332+P313:  If skin irritation occurs: Get medical advice/attention. *  P337+P313:  If eye irritation persists: Get medical advice/attention. *  P362+P364:  Take off contaminated clothing and wash it before reuse. *  P403+P233:  Store in a well-ventilated place. Keep container tightly closed. *  P405:  Store locked up. *  Safety Data Sheet (SDS):  ALWAYS consult the specific Safety Data Sheet (SDS) provided by the supplier for detailed hazard information, first aid measures, handling, storage, disposal, and regulatory information before use.