55937-99-0

Basic information

• Product Name: Beclobrate
• Synonyms: Beclobrate;Beclipur;Ethyl(±)-2-[[α(-(4-chlorophenyl)-4-tolyl]oxy]-2-methylbutyrate;Sgd-24774;Turec;2-[4-(4-Chlorobenzyl)phenoxy]-2-methylbutyric acid ethyl ester;Butanoic acid, 2-[4-[(4-chlorophenyl)Methyl]phenoxy]-2-Methyl-, ethyl ester;Ethyl 2-(4-(4-chlorobenzyl)phenoxy)-2-Methylbutanoate
• CAS NO: 55937-99-0
• Molecular Formula: C₂₀H₂₃ClO₃
• Molecular Weight: 346.852
• EINECS: 259-912-4
• Mol File: 55937-99-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: bp0.01-0.1 200-204°
• Flash Point: 149.6°C
• Appearance: /
• Density: 1.128g/cm³
• Vapor Pressure: 7.43E-08mmHg at 25°C
• Refractive Index: 1.541
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Beclobrate(CAS DataBase Reference)
• NIST Chemistry Reference: Beclobrate(55937-99-0)
• EPA Substance Registry System: Beclobrate(55937-99-0)

Safety Data

• Hazardous Substances Data: 55937-99-0(Hazardous Substances Data)

Usage

Description

Beclobrate is a hypolipidemic agent structurally related to clofibrate, which is useful in managing types IIa-V hyperlipoproteinemias and promoting the normalization of the atherogenic index.

Uses

Used in Pharmaceutical Industry:
Beclobrate is used as a hypolipidemic agent for managing types IIa-V hyperlipoproteinemias, helping to normalize the atherogenic index and reduce the risk of atherosclerosis and related cardiovascular diseases.

Originator

Siegfried AG (Switzerland)

Manufacturing Process

87.0 g (0.4 mol) of 4-chloro-4'-hydroxydiphenylmethane are heated together with 27.0 g (0.2 mol) of anhydrous potassium carbonate in 350 ml of anhydrous xylene for 30 min to reflux temperature, whereafter a solution of 83.5 g (0.4 mol) of 2-bromo-2-ethyl-2-methyl acetic acid ethyl ester in 50 ml of anhydrous xylene is added. The mixture is kept for 24 hours and with vigorous stirring at reflux temperature. After filtering off the precipitated potassium bromide and evaporating the solvent in a Buchi rotary evaporator, the residue is taken up in ether and extracted with normal sodium hydroxide solution. The ether extracts are washed with water, dried over MgSO4 and concentrated by evaporation. The brown oil (82.0 g) thereby obtained is dissolved in n-hexane and filtered through a column of 200 g of basic Al2O3. After evaporating the solvent and distillation at reduced pressure, 34.7 g of pure ethyl (+/-)-2-((α-(p-chlorophenyl)-p-tolyl)oxy)-2-methylbutyrate are obtained with the boiling point 200-204°C/0.01-0.1 mm Hg.

Therapeutic Function

Antihyperlipidemic

World Health Organization (WHO)

Beclobrate, an antihyperlipidaemic agent, was introduced into medicine in 1985. Although a causal relationship between the use of the drug and hepatic toxicity has not been established, the Intercantonal Office for the Control of Medicines has withdrawn marketing authorization since safer therapeutic alternatives are available. Beclobrate is not registered elsewhere.

InChI:InChI=1/C20H23ClO3/c1-4-20(3,19(22)23-5-2)24-18-12-8-16(9-13-18)14-15-6-10-17(21)11-7-15/h6-13H,4-5,14H2,1-3H3

Upstream product

• 5398-71-0 2-bromo-2-ethyl-2-methyl acetic acid ethyl ester 
• 52890-73-0 4-(4-chloro-benzyl)-phenol 
• 64-17-5 ethanol 
• 67-66-3 chloroform 
• 78-93-3 butanone 
• 5406-33-7 4-chlorobenzyl acetate 
• 7452-79-1 ethyl 2-methylbutyrate 
• 37155-52-5 1-(4-chlorobenzyl)-4-methoxybenzene 
• 622-95-7 4-chlorobenzyl bromide 
• 108-95-2 phenol 
• 100-66-3 methoxybenzene 
• 28139-26-6 ethyl 2-(4-bromophenoxy)-2-methylbutanoate 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 70039-17-7 4-(4-chlorophenylmethylene)-2,6-di-tert-butyl-2,5-cyclohexadien-1-one 

Downstream Products

• 70930-64-2 2-methyl-2-[4-(4'-chlorobenzyl)-phenoxy]-butanol 
• 71548-88-4 Beclobric acid 
• 81139-19-7 2-[4-(4-Chloro-benzyl)-phenoxy]-2-methyl-butyric acid 2-phenoxy-ethyl ester 
• 71548-98-6 2-[4-(4-Chloro-benzyl)-phenoxy]-2-methyl-butyric acid 3,3,5-trimethyl-cyclohexyl ester 
• 77985-10-5 2-[4-(4-Chloro-benzyl)-phenoxy]-2-methyl-butyric acid 2-acetylamino-ethyl ester 
• 71548-99-7 2-[4-(4-Chloro-benzyl)-phenoxy]-2-methyl-butyric acid benzyl ester 
• 81126-87-6 2-[4-(4-Chloro-benzyl)-phenoxy]-2-methyl-butyric acid isobutyl ester 
• 81126-86-5 n-Butyl 2-methyl-2-[p-(p'-chlorobenzyl)phenoxy]butyrate 
• 71548-95-3 2-[4-(4-Chloro-benzyl)-phenoxy]-2-methyl-butyric acid sec-butyl ester 
• 77985-12-7 n-Propyl 2-methyl-2-[p-(p'-chlorobenzyl)phenoxy]butyrate 
• 94740-32-6 t-Butyl 2-methyl-2-[p-(p'-chlorobenzyl)phenoxy]butyrate 
• 81126-85-4 Isopropyl 2-methyl-2-[p-(p'-chlorobenzyl)phenoxy]butyrate 
• 77985-11-6 Beclobrinsaeure-methylester 

Relevant articles and documents

Diarylmethane compounds as well as preparation method and application thereof

The invention discloses diarylmethane compounds as well as a preparation method and application thereof. The diarylmethane compounds have a molecular structural general formula as defined by a generalformula (I) in the description. The preparation method of the diarylmethane compounds comprises the steps of adding a benzyl halogenated hydrocarbon compound A and an arylboronic acid B into a reaction system containing an organic small-molecular catalyst, an alkali reagent and a solvent, and performing a reaction to prepare the compounds. The diarylmethane compounds provided by the invention contain electron withdrawing groups and an electron-donating group substituted diarylmethane basic structure, and can be widely used for synthesis of pharmaceutical intermediates, particularly polysubstituted methane compounds, and preparation of functional materials; and the preparation method has a simple process and low requirements for reaction conditions, the reaction process is safe and controllable, the atomic utilization rate and production efficiency are high, the regioselectivity and stereoselectivity of the products are efficiently ensured, a frontier science small-molecule organocatalysis concept is introduced, and the method is friendly to the environment.

B(C6F5)3 catalysed reduction of: Para -quinone methides and fuchsones to access unsymmetrical diaryl- and triarylmethanes: Elaboration to beclobrate

A mild and efficient method for the synthesis of unsymmetrical diaryl- and triarylmethanes through a B(C6F5)3 catalyzed reduction of para-quinone methides and fuchsones respectively, using the Hantzsch ester as a reducing source has been developed. Detailed mechanistic investigations revealed that the reaction actually proceeds through a Lewis acid-base pair complex derived from B(C6F5)3 and the Hantzsch ester.

Unsymmetrical diarylmethanes by ferroceniumboronic acid catalyzed direct friedel-crafts reactions with deactivated benzylic alcohols: Enhanced reactivity due to ion-pairing effects

The development of general and more atom-economical catalytic processes for Friedel-Crafts alkylations of unactivated arenes is an important objective of interest for the production of pharmaceuticals and commodity chemicals. Ferroceniumboronic acid hexafluoroantimonate salt (1) was identified as a superior air- and moisture-tolerant catalyst for direct Friedel-Crafts alkylations of a variety of slightly activated and neutral arenes with stable and readily available primary and secondary benzylic alcohols. Compared to the use of classical metal-catalyzed alkylations with toxic benzylic halides, this methodology employs exceptionally mild conditions to provide a wide variety of unsymmetrical diarylmethanes and other 1,1-diarylalkane products in high yield with good to high regioselectivity. The optimal method, using the bench-stable ferroceniumboronic acid salt 1 in hexafluoroisopropanol as cosolvent, displays a broader scope compared to previously reported catalysts for similar Friedel-Crafts reactions of benzylic alcohols, including other boronic acids such as 2,3,4,5-tetrafluorophenylboronic acid. The efficacy of the new boronic acid catalyst was confirmed by its ability to activate primary benzylic alcohols functionalized with destabilizing electron-withdrawing groups like halides, carboxyesters, and nitro substituents. Arene benzylation was demonstrated on a gram scale at up to 1 M concentration with catalyst recovery. Mechanistic studies point toward the importance of the ionic nature of the catalyst and suggest that factors other than the Lewis acidity (pKa) of the boronic acid are at play. A SN1 mechanism is proposed where ion exchange within the initial boronate anion affords a more reactive carbocation paired with the non-nucleophilic hexafluoroantimonate counteranion.