3-Chloro-1-phenyl-1-propanol RC00262

Manufacturer: Hangzhou Royalchem Co.,LTD.

Website:   www.cnroyalchem.com

Here is a detailed product description for  CAS 18776-12-0: (R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol :

Chemical Identity & Structure:

Systematic Name:  (2R)-α,α-Diphenyl-1-(2-pyrrolidinyl)methanol

Common Names:

(R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol

(R)-α,α-Diphenyl-2-pyrrolidinemethanol

(R)-(+)-Diphenylprolinol

(R)-Diphenylprolinol

(R)-2-(Diphenylhydroxymethyl)pyrrolidine

CBS Reagent Precursor / Catalyst Component:  Core precursor for the catalytic Corey-Bakshi-Shibata (CBS) reduction system.

CAS Registry Number:  18776-12-0

Molecular Formula:  C₁₇H₁₉NO

Molecular Weight:  253.34 g/mol

Structure:  Features a pyrrolidine ring (5-membered nitrogen heterocycle) with a chiral carbon atom (C2, R-configuration) bearing a hydroxymethyl group (-CH₂OH). This chiral carbon is also substituted with two phenyl groups (-C(C₆H₅)₂OH). The stereogenic center at C2 is specifically in the  (R)  configuration.

Stereochemistry:  High enantiomeric purity (typical ee >99%). The "(+)" designation indicates that this enantiomer exhibits a positive optical rotation (dextrorotatory).

Physical Properties:

Appearance:  Typically supplied as a white to off-white crystalline solid or powder.

Melting Point:  Reported values vary slightly (e.g., ~88-92 °C, 100-102 °C). Depends on purity and crystal form.

Optical Rotation:  [α]D²⁵ typically ranges from  +30° to +33° (c=1, CHCl₃)  or similar values (e.g., +35.2°).  Always verify the specific value provided with the batch.

Solubility:  Soluble in common organic solvents like dichloromethane (DCM), chloroform, tetrahydrofuran (THF), toluene, ethyl acetate, and methanol. Less soluble or insoluble in water.

Storage:  Store under inert atmosphere (Argon/Nitrogen) at 2-8 °C (refrigerated) to prevent degradation (e.g., oxidation). Protect from light and moisture. Desiccate.

Chemical Properties:

Functional Groups:  Secondary amine (pyrrolidine nitrogen), benzhydryl-type tertiary alcohol (chiral center), aromatic rings.

Chiral Auxiliary/Ligand:  Its primary significance lies in its role as a  precursor to the highly effective Corey-Bakshi-Shibata (CBS) catalyst  for enantioselective reduction of prochiral ketones.

CBS Catalyst Formation:  Reacts readily with borane (BH₃) derivatives (e.g., BH₃·THF, BH₃·SMe₂) to form the active oxazaborolidine catalyst in situ. The chiral environment provided by the  (R) -diphenylprolinol dictates the stereochemical outcome of the reduction, typically delivering the  (S) -alcohol product with high enantioselectivity.

Enantioselectivity:  The specific  (R) -enantiomer is essential for generating the catalyst that produces  (S) -secondary alcohols. The  (S) -enantiomer produces the opposite enantiomer catalyst.

Basicity:  The pyrrolidine nitrogen is moderately basic.

Stability:  The free amine/alcohol is generally stable if stored properly but can be sensitive to air oxidation over time. The borane complex is air/moisture sensitive.

Primary Applications:

Corey-Bakshi-Shibata (CBS) Reduction:  The  dominant and most important application . Used as the chiral controller in the catalytic enantioselective reduction of a vast array of prochiral ketones to chiral secondary alcohols with high enantiomeric excess (ee), often >95% and frequently >99%. This is a cornerstone methodology in modern asymmetric synthesis for pharmaceuticals, agrochemicals, fragrances, and fine chemicals.

Chiral Ligand/Organocatalyst:  Can act as a chiral ligand in other metal-catalyzed reactions or as a chiral organocatalyst in certain transformations due to its bifunctional nature (amine + alcohol).

Chiral Auxiliary:  Potential use as a chiral auxiliary in diastereoselective synthesis, though less common than its CBS role.

Chiral Resolving Agent:  Occasionally used for resolution of racemic acids via diastereomeric salt formation.

Handling & Safety:

GHS Classification:  Typically classified as:

Eye Irritation (Category 2A)

Skin Irritation (Category 2)

Safety Phrases:  Handle with care. Avoid contact with skin, eyes, and clothing. Avoid inhalation of dust. Use only in well-ventilated areas.

Personal Protective Equipment (PPE):  Wear safety glasses or goggles, chemical-resistant gloves, and a lab coat. Respiratory protection (dust mask) may be necessary when handling powders to minimize inhalation risk.

First Aid:  Flush eyes/skin with plenty of water if contact occurs. Seek medical advice if irritation persists. If inhaled, move to fresh air. If ingested, seek medical attention immediately; do not induce vomiting.

Stability & Reactivity:  Stable under recommended storage conditions. Incompatible with strong oxidizing agents and strong acids.

Always consult the specific Safety Data Sheet (SDS) provided by the supplier for the exact batch before handling.