114446-47-8

Basic information

• Product Name: (R)-3-Chloro-1-phenyl-1-(2-methylphenoxy)propane
• Synonyms: (R)-3-Chloro-1-phenyl-1-(2-methylphenoxy)propane;1-[(1R)-3-Chloro-1-phenylpropoxy]-2-methylbenzene
• CAS NO: 114446-47-8
• Molecular Formula: C₁₆H₁₇ClO
• Molecular Weight: 260.76
• Product Categories: Aromatics Compounds;Aromatics;Chiral Reagents;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Chiral Reagents, Intermediates, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 114446-47-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 375.403°C at 760 mmHg
• Flash Point: 179.533°C
• Appearance: /
• Density: 1.107g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (R)-3-Chloro-1-phenyl-1-(2-methylphenoxy)propane(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-Chloro-1-phenyl-1-(2-methylphenoxy)propane(114446-47-8)
• EPA Substance Registry System: (R)-3-Chloro-1-phenyl-1-(2-methylphenoxy)propane(114446-47-8)

Safety Data

• Hazardous Substances Data: 114446-47-8(Hazardous Substances Data)

Usage

Description

(R)-3-Chloro-1-phenyl-1-(2-methylphenoxy)propane is a chiral intermediate used in the synthesis of Desmethyl atomoxetine. It is a colorless oil with unique chemical properties that make it valuable in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
(R)-3-Chloro-1-phenyl-1-(2-methylphenoxy)propane is used as a chiral intermediate for the synthesis of Desmethyl atomoxetine, a compound with potential applications in the treatment of attention deficit hyperactivity disorder (ADHD) and other related conditions. Its role in the synthesis process is crucial for the development of effective medications that can help improve the quality of life for patients suffering from these disorders.
As a chiral intermediate, (R)-3-Chloro-1-phenyl-1-(2-methylphenoxy)propane plays a significant role in the production of enantiomerically pure compounds, which are essential in the pharmaceutical industry due to their potential for increased efficacy and reduced side effects compared to their racemic counterparts.

InChI:InChI=1/C16H17ClO/c1-13-7-5-6-10-15(13)18-16(11-12-17)14-8-3-2-4-9-14/h2-10,16H,11-12H2,1H3/t16-/m1/s1

Upstream product

• 100306-34-1 3-chloro-1-phenylpropanol 
• 95-48-7 ortho-cresol 
• 936-59-4 3-chloropropiophenone 
• 18776-12-0 3-chloro-1-phenyl-propan-1-ol 
• 293322-40-4 3-Cloro-1-phenylpropyl butanoate 
• 141987-54-4 1-Phenyl-3-chlor-propyl-monochloracetat 
• 142037-19-2 Chloro-acetic acid (S)-3-chloro-1-phenyl-propyl ester 
• 71-43-2 benzene 
• 95-52-3 2-Fluorotoluene 
• 100306-33-0 (1R)-3-chloro-1-phenylpropanol 

Downstream Products

• 82248-59-7 atomoxetine hydrochloride 
• 105314-52-1 (R)-tomoxetine 

Relevant articles and documents

Preparation method of cefamoxetine hydrochloride

The invention discloses a preparation method of tamoxidectin hydrochloride, belongs to the technical field of drug synthesis, and uses 3 - chlorine -1 - phenylpropanone as a raw material to undergo a reduction reaction. The synthesis route has the advantages of few reaction steps, mild reaction conditions,3 - simple 2 - operation, cheap -3 - and easily available raw materials, and low production cost 3 - and -1 - R-chloro - N - phenylpropanone is used as a raw material.

Asymmetric reduction of prochiral ketones using in situ generated oxazaborolidine derived from (1S,2S,3R,4R)-3-amino-7,7-dimethoxynorbornan-2-ol. An efficient synthesis of enantiopure (R)-tomoxetine

In this work, we report our results on the asymmetric reduction of prochiral aromatic and aliphatic ketones 3, 5-8 catalyzed by the novel in situ generated oxazaborolidine 2 derived from (1S,2S,3R,4R)-3-amino-7,7- dimethoxybornan-2-ol (1) and BH3?Me2S. This methodology was applied to the synthesis of the anti-depressant drug (R)-tomoxetine in three steps and 47% overall yield from 3-chloropropiophenone (3h). Catalytic asymmetric reduction of prochiral ketones was examined in the presence of chiral oxazaborolidine catalyst 2 prepared in situ from (1S,2S,3R,4R)-3-amino-7,7-dimethoxynorbornan-2-ol (1). The optically active secondary alcohols were generally obtained in moderate to high enantiomeric excesses (ee 43-95%) and good yields (75-94%), except for ketones bearing electron-withdrawing groups. The methodology was applied to the synthesis of enantiopure (R)-tomoxetine, a potent anti-depressant drug.

Iodinated tomoxetine derivatives as selective ligands for serotonin and norepinephrine uptake sites

In order to develop selective radioactive ligands for the study of presynaptic monoamine uptake sites, iodinated derivatives of tomoxetine were synthesized and evaluated in radioligand binding assays. Iodotomoxetine derivatives showed high affinity for serotonin (5-HT) uptake sites using a rat cortical membrane preparation. Compound 1R, (R)-(-)-N-methyl-3-(4-iodo-2- methyl]phenoxy)-3-phenylpropanamine, was the most potent and showed high stereoselectivity for 5-HT uptake sites (K(i), R isomer = 0.65 nM, S isomer = 13.9 nM). Changing the position of the methyl group or eliminating the methyl group at the phenoxy ring resulted in a loss of stereoselectivity. Substitution of the methyl group of tomoxetine with iodine gave the R and S isomers of N-methyl-3-(2-iodophenoxy)-3-phenylpropanamine 4R and 4S. These compounds displayed stereoselectivity for the norepinephrine (NE) (K(i) values = 0.24 and 9.35 nM for R and S isomers, respectively). The in vitro binding data suggest that 1R and 4R are potential radioiodinated ligands for pharmacological studies of 5-HT and NE uptake sites, respectively.