56782-68-4

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(-)-1-(4-CHLOROPHENYL)ETHYLAMINE-HCl is used as a key intermediate in the synthesis of various medications for the treatment of mental health disorders such as depression and anxiety. Its chiral nature allows for the development of enantiomer-specific drugs, which can have different therapeutic effects and reduce potential side effects.
Used in Drug Development:
(S)-(-)-1-(4-CHLOROPHENYL)ETHYLAMINE-HCl is employed in the development of new drugs for neurological and psychiatric conditions, where its unique structure and properties can contribute to the discovery of innovative therapeutic agents with improved efficacy and safety profiles.
Used in Chemical Research:
(S)-(-)-1-(4-CHLOROPHENYL)ETHYLAMINE-HCl is used as a research tool in the study of the chemical and biological properties of chiral amines, aiding in the understanding of their interactions with biological targets and their potential applications in various fields.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-(-)-1-(4-CHLOROPHENYL)ETHYLAMINE-HCl serves as a versatile building block for the creation of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals, due to its reactive amine and chloride functionalities.

Upstream product

• 1164111-41-4 C₈H₈ClN*ClH 
• 99-91-2 para-chloroacetophenone 
• 4187-56-8 (S)-1-(p-chlorophenyl)ethylamine 

Relevant academic research and scientific papers

Chiral Bronsted Acids Catalyze Asymmetric Additions to Substrates that Are Already Protonated: Highly Enantioselective Disulfonimide-Catalyzed Hantzsch Ester Reductions of NH-Imine Hydrochloride Salts

While imines are frequently used substrates in asymmetric Bronsted acid catalysis, their corresponding salts are generally considered unsuitable reaction partners. Such processes are challenging because they require the successful competition of a catalytic amount of a chiral anion with a stoichiometric amount of an achiral one. We now show that enantiopure disulfonimides enable the asymmetric reduction of N-H imine hydrochloride salts using Hantzsch esters as hydrogen source. Our scalable reaction delivers crystalline primary amine salts in great efficiency and enantioselectivity and the discovery suggests potential of this approach in other Bronsted acid catalyzed transformations of achiral iminium salts. Kinetic studies and acidity data suggest a bifunctional catalytic activation mode.

Development of an in situ-Product Crystallization (ISPC)-Concept to Shift the Reaction Equilibria of Selected Amine Transaminase-Catalyzed Reactions

The synthesis of enantiopure amines via amine transaminases involves several challenges including unfavorable reaction equilibria and product inhibition. Described here is a non-catalytic approach to overcome such problems by using an in situ-product crystallization (ISPC) to selectively remove a targeted product amine from an amine transaminase-catalyzed reaction. The continuous removal of the product amine from its reaction solution as a barely soluble salt effectively yields a displacement of the reaction equilibrium towards the products and facilitates a simple downstream processing approach via filtration. The targeted product amine is eventually obtained from the salt, while the counterion compound can be easily recycled.

Rhodium-catalyzed asymmetric hydrogenation of unprotected NH imines assisted by a thiourea

Asymmetric hydrogenation of unprotected NH imines catalyzed by rhodium/bis(phosphine)-thiourea provided chiral amines with up to 97% yield and 95% ee. 1HNMR studies, coupled with control experiments, implied that catalytic chloride-bound intermediates were involved in the mechanism through a dual hydrogen-bonding interaction. Deuteration experiments proved that the hydrogenation proceeded through a pathway consistent with an imine.