(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate RC00231

Manufacturer: Hangzhou Royalchem Co.,LTD.

Website:   www.cnroyalchem.com

【 Providing a complete set of intermediates and impurities for Ticagrelor 】

【 Providing a complete set of intermediates and impurities for Ticagrelor 】

【 Providing a complete set of intermediates and impurities for Ticagrelor 】

Here is a detailed product description for  376608-71-8: (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate , based on the provided information and chemical structure analysis:

1. Chemical Identification & Nomenclature

CAS Registry Number:  376608-71-8

Systematic Name:  (1R,2S)-2-(3,4-Difluorophenyl)cyclopropan-1-amine (2R)-2-hydroxy-2-phenylacetate

Common/Synonym:  (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Mandelate

Molecular Structure:  This compound is a  diastereomeric salt  formed between:

The Chiral Amine:  (1R,2S)-2-(3,4-Difluorophenyl)cyclopropan-1-amine (the "free base").

The Chiral Counterion:  (2R)-2-Hydroxy-2-phenylacetic acid (Pharmaceutical name:  (2R)-Mandelic Acid ).

Molecular Formula:  Likely  C₁₇H₁₆F₂N O₃  (Combines C₉H₉F₂N [amine] + C₈H₈O₃ [mandelic acid] - H₂O [salt formation])

Molecular Weight:  Likely ~ 320.32 g/mol (Calculated from formula C₁₇H₁₆F₂N O₃). 

2. Structural Characteristics & Stereochemistry

Core Scaffold:  Features a  cyclopropylamine ring  substituted at the 2-position with a  3,4-difluorophenyl group .

Critical Chirality:

The cyclopropylamine has  two chiral centers  with defined  absolute configurations: (1R,2S) . This specific stereoisomer is crucial for biological activity (often seen in antidepressants like Vilazodone/Vortioxetine intermediates).

The mandelic acid counterion also has  one chiral center  with defined  absolute configuration: (2R) . This makes the salt a  diastereomeric complex .

Counterion Purpose:  The (2R)-mandelate is typically used for  chiral resolution  or  purification  of the desired (1R,2S)-amine enantiomer via diastereomeric salt crystallization. It may also aid in crystallization, stability, or handling of the free amine.

Functional Groups:  Primary amine (cationic, protonated), cyclopropane ring, difluorinated aromatic ring, carboxylate (anionic), secondary alcohol, phenyl ring.

3. Physical Properties (Typical Expectations)

Appearance:  White to off-white crystalline powder (common for purified diastereomeric salts).

Melting Point:  Expected to have a sharp melting point characteristic of a crystalline diastereomer, typically >100°C (exact value requires experimental measurement).

Solubility:

Water:  Slightly soluble to sparingly soluble (depends on pH).

Organic Solvents:  Soluble in polar organic solvents (e.g., Methanol, Ethanol, Ethyl Acetate, Dichloromethane, DMSO). Less soluble in non-polar solvents (e.g., Hexane, Toluene).

Optical Rotation:  Exhibits a specific optical rotation  [α]D  at a specified temperature and concentration due to the defined chirality of both components. The exact value is a key identifier for the specific diastereomer. (e.g.,  [α]D²⁵ = +XX° (c=1.0, Methanol)  - XX requires experimental data).

Stability:  Sensitive to strong acids, strong bases, strong oxidizing agents, and potentially light. Should be stored under inert conditions. 

4. Handling, Storage & Safety

Handling:  Use in a well-ventilated fume hood. Wear appropriate PPE (lab coat, safety glasses, gloves - nitrile recommended). Avoid inhalation of dust and contact with skin/eyes. Handle as potentially hazardous.

Storage:  Store  tightly sealed  in the original container under an  inert atmosphere (e.g., N₂ or Argon)  at  -20°C to +4°C (preferably frozen) . Protect from  light  and  moisture .

Safety Data:  A  Safety Data Sheet (SDS)  specific to this CAS number and supplier must be consulted prior to handling. Hazards typically include:

Irritant:  May cause skin, eye, and respiratory tract irritation.

Health Hazard:  Potential toxicity if swallowed, inhaled, or absorbed through skin. Specific target organ effects (e.g., CNS) are possible based on the pharmacologically active amine core.

Stability:  Stable under recommended storage conditions. Incompatible with strong acids, bases, oxidizers.

5. Primary Applications & Significance

Key Pharmaceutical Intermediate:  This specific diastereomeric salt is  primarily used in the synthesis of modern antidepressants , most notably as a high-purity precursor to the active pharmaceutical ingredient (API)  Vilazodone  or its analogs/intermediates. The (1R,2S) stereochemistry of the cyclopropylamine is essential for the desired biological activity.

Chiral Resolution:  The salt form itself is often an intermediate step in the  chiral purification  process of the (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine free base using (2R)-mandelic acid.

Research & Development:  Used in medicinal chemistry research focusing on Serotonin Receptor Modulators (e.g., 5-HT₁A agonists/antagonists, SERT inhibitors).