53542-78-2

Basic information

• Product Name: Ethanol, 2-(4-chlorophenoxy)-, methanesulfonate
• CAS NO: 53542-78-2
• Molecular Formula: C9H11ClO4S
• Molecular Weight: 250.703
• Mol File: 53542-78-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Ethanol, 2-(4-chlorophenoxy)-, methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanol, 2-(4-chlorophenoxy)-, methanesulfonate(53542-78-2)
• EPA Substance Registry System: Ethanol, 2-(4-chlorophenoxy)-, methanesulfonate(53542-78-2)

Safety Data

• Hazardous Substances Data: 53542-78-2(Hazardous Substances Data)

Upstream product

• 106-48-9 4-chloro-phenol 
• 1892-43-9 2-(4-chlorophenoxy)ethanol 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 65686-13-7 2-(4-chlorophenoxy)-N-methylethan-1-amine 
• 69183-22-8 {4-[2-(4-Chloro-phenoxy)-ethoxy]-phenyl}-(4-cyclohexyl-phenoxy)-acetic acid methyl ester 
• 69183-23-9 {4-[2-(4-Chloro-phenoxy)-ethoxy]-phenyl}-(4-trifluoromethyl-phenoxy)-acetic acid methyl ester 
• 69182-91-8 {4-[2-(4-Chloro-phenoxy)-ethoxy]-phenyl}-(3-dimethylamino-phenoxy)-acetic acid methyl ester 
• 69182-90-7 (4-Chloro-phenoxy)-{4-[2-(4-chloro-phenoxy)-ethoxy]-phenyl}-acetic acid methyl ester 
• 69182-89-4 Bromo-{4-[2-(4-chloro-phenoxy)-ethoxy]-phenyl}-acetic acid methyl ester 
• 69182-88-3 {4-[2-(4-Chloro-phenoxy)-ethoxy]-phenyl}-acetic acid methyl ester 

Relevant articles and documents

Development of novel phenoxyalkylpiperidines as high-affinity Sigma-1 (σ1) receptor ligands with potent anti-amnesic effect

The sigma-1 (σ1) receptor plays a significant role in many normal physiological functions and pathological disease states, and as such represents an attractive therapeutic target for both agonists and antagonists. Here, we describe a novel series of phenoxyalkylpiperidines based on the lead compound 1-[ω-(4-chlorophenoxy)ethyl]-4-methylpiperidine (1a) in which the degree of methylation at the carbon atoms alpha to the piperidine nitrogen was systematically varied. The affinity at σ1 and σ2 receptors and at Δ8-Δ7 sterol isomerase (SI) ranged from subnanomolar to micromolar Ki values. While the highest-affinity was displayed at the σ1, the increase of the degree of methylation in the piperidine ring progressively decreased the affinity. The subnanomolar affinity 1a and 1-[ω-(4-methoxyphenoxy)ethyl]-4-methylpiperidine (1b) displayed potent anti-amnesic effects associated with σ1 receptor agonism, in two memory tests. Automated receptor–small-molecule ligand docking provided a molecular structure-based rationale for the agonistic effects of 1a and 1b. Overall, the class of the phenoxyalkylpiperidines holds potential for the development of high affinity σ1 receptor agonists, and compound 1a, that appears as the best in class (exceeding by far the activity of the reference compound PRE-084) deserves further investigation.

Convenient Continuous Flow Synthesis of N-Methyl Secondary Amines from Alkyl Mesylates and Epoxides

The first continuous flow process was developed to synthesize N-methyl secondary amines from alkyl mesylates and epoxides via a nucleophilic substitution using aqueous methylamine. A variety of N-methyl secondary amines were produced in good to excellent yields, including a number of bioactive compounds or their precursors. Up to 10.6 g (88% yield) of an N-methyl secondary amine was produced in 140 min process time. The amination procedure included an in-line workup, and the starting mesylate material was also produced in continuous flow from the corresponding alcohol. Finally, an in-line process combining the mesylate synthesis and nucleophilic substitution was developed.