(1S)-2-chloro-1-(3,4-difluorophenyl)-1-ethanol RC00252

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 (1S)-2-chloro-1-(3,4-difluorophenyl)ethanol (CAS # 1006376-60-8)   :

Product Name:  (S)-2-Chloro-1-(3,4-difluorophenyl)ethanol 

CAS Registry Number:  1006376-60-8 

Synonyms:

(1S)-2-Chloro-1-(3,4-difluorophenyl)ethanol 

(S)-1-(3,4-Difluorophenyl)-2-chloroethanol

(S)-2-Chloro-1-(3,4-difluorophenyl)ethan-1-ol

β-Chloro alcohol intermediate

Molecular Formula:  C₈H₇ClF₂O  Molecular Weight:  204.59 g/mol

Appearance:  Typically supplied as a colorless to pale yellow viscous liquid or low-melting solid. Color can vary slightly depending on purity and age.  Purity:  Commonly available at ≥95% (determined by HPLC or GC), with chiral purity typically ≥95% ee (% enantiomeric excess). Higher purities (e.g., 97%, 98%, 99%, 99% ee) are often available upon request or specific synthesis.  Solubility:  Soluble in common organic solvents such as dichloromethane (DCM), ethyl acetate (EtOAc), tetrahydrofuran (THF), dimethylformamide (DMF), dimethyl sulfoxide (DMSO), and alcohols (methanol, ethanol). Sparingly soluble or insoluble in water.

Key Characteristics:

Chirality:  Exists as a single enantiomer with (S)-configuration at the benzylic carbon. This is crucial for stereoselective synthesis.

Functional Groups:

β-Halo Alcohol (Chloroalcohol):  The presence of both the chlorine atom and the hydroxyl group on adjacent carbon atoms makes this a reactive synthon. This moiety is prone to ring closure (epoxide formation) under basic conditions or participation in nucleophilic substitution reactions.

Aryl Fluorides:  The 3,4-difluorophenyl group offers metabolic stability, lipophilicity, and potential for specific binding interactions, making it a common pharmacophore in medicinal chemistry.

Reactivity:  Primarily used as a versatile chiral building block.

The chlorine atom can be displaced by nucleophiles (e.g., amines, azides, thiols) leading to chiral β-substituted alcohols.

Base treatment readily cyclizes it to form the corresponding (S)-epoxide: (S)-1-(3,4-Difluorophenyl)oxirane, another valuable chiral synthon.

The hydroxyl group can be protected (e.g., silylation, acetylation) or oxidized.

The aromatic ring can potentially undergo electrophilic substitution under controlled conditions, though the fluorines are ortho/para directing but deactivating.

Storage:

Store tightly sealed in a cool, dry, and well-ventilated place.

Recommended storage temperature:   -20°C  or below for long-term stability. Store under an inert atmosphere (Argon or Nitrogen) to minimize oxidation and moisture absorption.

Protect from light to prevent potential decomposition.

Handling & Safety:

Hazard Statements (GHS - Typical):

H315:  Causes skin irritation.

H319:  Causes serious eye irritation.

H335:  May cause respiratory irritation.

H302:  Harmful if swallowed.

H317:  May cause an allergic skin reaction (Sensitization potential common with β-chloro alcohols).

Precautionary Statements:

P261:  Avoid breathing dust/fume/gas/mist/vapours/spray.

P264:  Wash skin thoroughly after handling.

P270:  Do not eat, drink or smoke when using this product.

P271:  Use only outdoors or in a well-ventilated area.

P280:  Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312:  IF SWALLOWED: Call a POISON CENTER/doctor/… IF you feel unwell.

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.

P310:  Immediately call a POISON CENTER/doctor/…

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.

Personal Protective Equipment (PPE):  Always wear appropriate gloves (e.g., nitrile), safety goggles, and lab coat. Use in a fume hood.

Applications/Primary Use:  (S)-2-Chloro-1-(3,4-difluorophenyl)ethanol is exclusively used as a  high-value chiral building block (synthon) in organic synthesis, particularly in pharmaceutical research and development.

Key Intermediate:  Primarily for synthesizing enantiomerically pure compounds, especially active pharmaceutical ingredients (APIs) or their advanced intermediates.

Epoxide Precursor:  Direct precursor to (S)-1-(3,4-Difluorophenyl)oxirane, a crucial chiral epoxide used in nucleophilic ring-opening reactions.

Pharmacophore Integration:  The chiral center combined with the 3,4-difluorophenyl moiety is structurally relevant for targeting various biological receptors. It is frequently employed in the synthesis of potential drugs acting on the central nervous system (CNS), such as:

Selective noradrenaline reuptake inhibitors (NRIs).

Serotonin-norepinephrine reuptake inhibitors (SNRIs).

Adrenergic receptor ligands (e.g., β-blockers, β-agonists - analogues).

Medicinal Chemistry:  Used to introduce the chiral 2-hydroxy-2-(3,4-difluorophenyl)ethylamine pharmacophore into target molecules via nucleophilic displacement of the chloride or via the epoxide route.