130194-43-3

Basic information

• Product Name: (S)-3-PHENYL-3-(4-TRIFLUOROMETHYL-PHENOXY)-PROPYLAMINE HYDROCHLORIDE
• Synonyms: (S)-3-[4-(TRIFLUOROMETHYL)PHENOXY]-3-PHENYLPROPAN-1-AMINE HYDROCHLORIDE;(S)-3-PHENYL-3-(4-TRIFLUOROMETHYL-PHENOXY)-PROPYLAMINE HYDROCHLORIDE;(S)-3-Phenyl-3-(4-(trifluoroMethyl)phenoxy)propan-1-aMine hydrochloride;(R)-3-Phenyl-3-(4-trifluoromethyl-phenoxy)-propylamine
• CAS NO: 130194-43-3
• Molecular Formula: C₁₆H₁₆F₃NO
• Molecular Weight: 295.3
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 130194-43-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 381.069°C at 760 mmHg
• Flash Point: 184.264°C
• Appearance: /
• Density: 1.205g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.526
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (S)-3-PHENYL-3-(4-TRIFLUOROMETHYL-PHENOXY)-PROPYLAMINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-PHENYL-3-(4-TRIFLUOROMETHYL-PHENOXY)-PROPYLAMINE HYDROCHLORIDE(130194-43-3)
• EPA Substance Registry System: (S)-3-PHENYL-3-(4-TRIFLUOROMETHYL-PHENOXY)-PROPYLAMINE HYDROCHLORIDE(130194-43-3)

Safety Data

• Hazardous Substances Data: 130194-43-3(Hazardous Substances Data)

Usage

Description

(S)-3-PHENYL-3-(4-TRIFLUOROMETHYL-PHENOXY)-PROPYLAMINE HYDROCHLORIDE is a chiral compound with a complex molecular structure, featuring a phenyl group, a trifluoromethylphenoxy group, and a propylamine moiety. It is a pale yellow oil at room temperature, indicating its lipophilic nature and potential for dissolution in organic solvents.

Uses

Used in Pharmaceutical Industry:
(S)-3-PHENYL-3-(4-TRIFLUOROMETHYL-PHENOXY)-PROPYLAMINE HYDROCHLORIDE is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to serve as a building block for the development of new drugs with potential therapeutic applications.
Used in Antidepressant Formulation:
As a metabolite of Fluoxetine, a selective serotonin reuptake inhibitor (SSRI), (S)-3-PHENYL-3-(4-TRIFLUOROMETHYL-PHENOXY)-PROPYLAMINE HYDROCHLORIDE is used as an antidepressant. It contributes to the overall efficacy of Fluoxetine in treating depression by modulating the levels of serotonin in the brain, thereby improving mood and reducing symptoms of depression.
Used in Chemical Research:
Due to its chiral nature and complex structure, (S)-3-PHENYL-3-(4-TRIFLUOROMETHYL-PHENOXY)-PROPYLAMINE HYDROCHLORIDE is also used in chemical research for studying the synthesis of enantiomers and their potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C16H16F3NO/c17-16(18,19)13-6-8-14(9-7-13)21-15(10-11-20)12-4-2-1-3-5-12/h1-9,15H,10-11,20H2/t15-/m1/s1

Upstream product

• 98-56-6 4-chlorobenzotrifluoride 
• 138750-31-9 (1R)-3-amino-1-phenyl-1-propanol 
• 100-42-5 styrene 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 73627-97-1 (R)-3-phenyl-3-hydroxypropanenitrile 
• 40435-14-1 (S)-1-phenyl-2-(tosyloxy)ethanol 
• 96-09-3 styrene oxide 
• 73627-97-1 3-hydroxy-3-phenylpropanenitrile 
• 198561-42-1 (R)-3-acetyloxy-3-phenylpropanenitrile 
• 83891-03-6 norfluoxetine 
• 878663-12-8 (R)-1-phthalimido-3-(4-trifluormethyl-phenoxy)-3-phenyl-propane 
• 402-45-9 4-hydroxybenzotrifluoride 
• 100306-34-1 3-chloro-1-phenylpropanol 

Downstream Products

• 54910-89-3 (R)-fluoxetine 
• 114247-09-5 (R)-fluoxetine hydrochloride 
• 1159998-50-1 (R)-2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-N-(3-phenyl-[3-(4-trifluromethyl)phenoxy]propyl)propanamide 
• 878663-15-1 C₃₇H₄₂F₃N₃O₄ 

Relevant articles and documents

Stereoselective inhibition of serotonin re-uptake and phosphodiesterase by dual inhibitors as potential agents for depression

Multi-target compounds where more than one functional activity is incorporated into the same molecule may have advantages in treating disease states. Selective serotonin re-uptake inhibitors (SSRIs)a (i.e., (R)- and (S)-norfluoxetine) were chemically linked to a PDE4 inhibitor via a five carbon bridge. The new dual PDE4 inhibitor/SSRIs (i.e., (R)-8 and (S)-8) showed moderately potent but highly selective serotonin re-uptake inhibition (IC50 values of 173 and 42 nM, respectively) in vitro. The dual PDE4 inhibitor/SSRIs (R)-8 and (S)-8 also inhibited PDE4D2 (i.e., Ki values of 106 and 253 nM, respectively). Due to the synergistic functional activity, PDE4 inhibitor/SSRIs may be effective in treating diseases such as depression.

MODULATORS OF CENTRAL NERVOUS SYSTEM NEUROTRANSMITTERS

Disclosed are agents having pharmacological activity against cellular receptors and intracellular singaling, particularly receptors and sigaling pathways of central nervous system (CNS) neurotransmitters. Also disclosed are related methods and compositions for the treatment or prevention of diseases or disorders using the agents.

Chemoenzymatic synthesis2 of both enantiomers of fluoxetine, tomoxetine and nisoxetine: Lipase-catalyzed resolution of 3-aryl-3-hydroxypropanenitriles

A facile preparation of (±)-3-hydroxy-3-phenylpropanenitrile has been carried out by ring-opening of styrene oxide with NaCN in aqueous ethanol. Subsequent kinetic resolution of this material via lipase-mediated transesterification gave the S-alcohol and R-acetate in excellent yields and high enantioselectivities, particularly with lipase PS-C 'Amano' II. The effect of solvents and immobilization of the lipase has also been investigated. It is interesting to note that the use of immobilized lipase for this transesterification process in hydrophobic solvents (diisopropyl ether, toluene and hexane) enhanced the reaction rate drastically and gave optimal yields with high enantioselectivity (>99%). Moreover, enantiopure 3-hydroxy-3-phenylpropanenitrile products have been converted via enantioconvergent routes into the (R)- and (S)-enantiomers of the important anti-depressants fluoxetine, tomoxetine, nisoxetine and norfluoxetine.