114247-09-5

Basic information

• Product Name: R-(-)-Fluoxetine hydrochloride
• Synonyms: Unii-7C4D25st1t;(R)-N-Methyl-3-(4-trifluoroMethylphenoxy)-3-phenylpropylaMine Hydrochloride;(γR)-N-Methyl-γ-[4-(trifluoroMethyl)phenoxy]benzenepropanaMine Hydrochloride;Fluoxetine R-IsoMer HCl;(R)-N-Methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propylamine hydrochloride;(R)-3-[4(TRIFLUOROMETHYL)PHENOXY]-N-METHYL-3-PHENYLPROPAN-1-AMINE HYDROCHLORIDE;(R)-FLUOXETINE;R-(-)-FLUOXETINE HYDROCHLORIDE
• CAS NO: 114247-09-5
• Molecular Formula: C₁₇H₁₈F₃NO*ClH
• Molecular Weight: 345.79
• Product Categories: Amines;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Biogenic Amine Transport Inhibitors;Biogenic Amine Transport InhibitorsObesity Research;Neurotransmission;Neurotransmission (Obesity);Neurotransmitters
• Mol File: 114247-09-5.mol
• Article Data: 20

Chemical Properties

• Melting Point: 126-129°C
• Boiling Point: 395.1 °C at 760 mmHg
• Flash Point: 192.8 °C
• Appearance: white/solid
• Vapor Pressure: 1.88E-06mmHg at 25°C
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility: H2O: 20 mg/mL, soluble
• CAS DataBase Reference: R-(-)-Fluoxetine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: R-(-)-Fluoxetine hydrochloride(114247-09-5)
• EPA Substance Registry System: R-(-)-Fluoxetine hydrochloride(114247-09-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-38-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 114247-09-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

As a selective serotonin reuptake inhibitor (SSRI), R-(-)-Fluoxetine hydrochloride can be used as an antidepressant.

Definition

ChEBI: A hydrochloride obtained by reaction of (R)-fluoxetine with one equivalent of hydrochloric acid.

InChI:InChI=1/C17H18F3NO.ClH/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20;/h2-10,16,21H,11-12H2,1H3;1H/t16-;/m1./s1

Upstream product

• 98-56-6 4-chlorobenzotrifluoride 
• 74-89-5 methylamine 
• 51699-49-1 3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate 
• 3506-36-3 3-dimethylaminopropiophenone 
• 455-13-0 4-Iodobenzotrifluoride 
• 115290-81-8 (R)-N-methyl-3-phenyl-3-hydroxypropylamine 
• 127073-84-1 (R)-3-iodo-1-phenyl-1-propanol 
• 100306-33-0 (1R)-3-chloro-1-phenylpropanol 
• 936-59-4 3-chloropropiophenone 
• 402-45-9 α,α,α-trifluoro-p-cresol 
• 100306-34-1 3-chloro-1-phenylpropanol 
• 138110-76-6 (R)-3-(4-trifluoromethylphenoxy)-3-phenylprop-1-yl methanesulfonate 
• 138110-77-7 (R)-3-Iodo-3-(4-trifluoromethylphenoxy)propane 
• 115290-77-2 (1S) 3-phenyl-3-hydroxypropyl methanesulfonate 

Downstream Products

• 1159998-53-4 (R)-[4-(4-chlorobenzoyl)phenoxy]-N,2-dimethyl-N-[3-phenyl-3-(4-trifluoromethyl)phenoxy]propanamide 

Relevant articles and documents

Direct catalytic asymmetric aldol reaction of thioamides: A concise asymmetric synthesis of (R)-fluoxetine

A direct catalytic asymmetric aldol reaction of aromatic aldehydes and thioamides is described. A soft Lewis acid/hard Bronsted base cooperative catalyst comprising (R,R)-Ph-BPE/[Cu(CH3CN)4]PF 6/Li(OC6H4-p-OMe) promoted the title reaction efficiently, triggered by in situ generation of the active thioamide enolate through a soft-soft interaction of Cu(I) and the thioamide. The aldol product was transformed into (R)-fluoxetine, an antidepressant agent.

AN EFFICIENT METHOD FOR PREPARING 3-ARYLOXY-3- ARYLPROPYLAMINES AND THEIR OPTICAL STEREOISOMERS

Provided is an efficient method for the preparation of 3-aryloxy-3- arylpropylamines, their optical stereoisomers, and pharmaceutically acceptable salts thereof. The process allows for the isolation of 3-aryloxy-3- arylpropylamines in high yield and purity. The present invention further relates to a process for producing fluoxetine, tomoxetine, norfluoxetine, duloxetine, nisoxetine, and their optically enriched (R)- and (S)-enantiomers.

Pd-catalyzed kinetic resolution of benzylic alcohols: A practical synthesis of (R)-tomoxetine and (S)-fluoxetine hydrochlorides

A convenient synthetic route to (R)-tomoxetine hydrochloride (90% ee) and (S)-fluoxetine hydrochloride (84% ee) is described. (S)-3-Phenyl-3-hydroxypropyl p-toluenesulphonate, the key intermediate, is obtained by the oxidative kinetic resolution of the corresponding racemic 3-phenyl-3-hydroxypropyl p-toluenesulphonate using (-)-sparteine/Pd(II)/O2 (1 atm) catalytic system.