154477-54-0

Basic information

• Product Name: Methyl 2-(4-(4-chlorobutanoyl)phenyl)-2-methylpropanoate
• Synonyms: METHYL 2-(4-[4-(4-BENZHYDRYLOXY-PIPERIDIN-1-YL)-BUTYRYL]-PHENYL)-2-METHYLPROPIONATE;METHYL [4-(4-CHLORO-1-OXOBUTYL)]-A,A-DIMETHYL PHENYLACETATE;2-[4-(4-CHLORO-1-OXOBUTYL)-PHENYL]-2-METHYLPROPIONIC ACID METHYL ESTER;Methyl 4-(4-chloro-1-oxobutyl)-alpha,alpha-dimethylbenzeneacetate;METHYL [4-(4-CHLORO-1-OXOBUTYL)]-A,A-DIMETHYL PHENYLACETATE(OR)2-[4-(4-CHLORO-1-OXOBUTYL)-PHENYL]-2-METHYLPROPIONIC ACID METHYL ESTER;4-(4-CHLORO-1-OXOBUTYL)-ALPHA,ALPHA-DIMETHYLBENZOIC ACID METHYL ESTER;2-[4-(4-Chlorobutyryl)phenyl]-2-methylpropionic acid methyl ester;4-(4-Chloro-1-oxobutyl)-α,a-dimethylbenzeneacetic Acid Methyl Ester
• CAS NO: 154477-54-0
• Molecular Formula: C₁₅H₁₉ClO₃
• Molecular Weight: 282.76
• Product Categories: Aromatics Compounds;Aromatics;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 154477-54-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 396.513 °C at 760 mmHg
• Flash Point: 149.639 °C
• Appearance: Brown oil
• Density: 1.121
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.508
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Methyl 2-(4-(4-chlorobutanoyl)phenyl)-2-methylpropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-(4-(4-chlorobutanoyl)phenyl)-2-methylpropanoate(154477-54-0)
• EPA Substance Registry System: Methyl 2-(4-(4-chlorobutanoyl)phenyl)-2-methylpropanoate(154477-54-0)

Safety Data

• Hazardous Substances Data: 154477-54-0(Hazardous Substances Data)

Usage

Chemical Properties

Brown Oil

Uses

Different sources of media describe the Uses of 154477-54-0 differently. You can refer to the following data:
1. Fexofenadine intermediate. Antihistaminic and antiallergic agent
2. 4-(4-Chloro-1-oxobutyl)-α,α-dimethylbenzeneacetic Acid Methyl Ester is a fexofenadine (F322490) intermediate. Antihistaminic and antiallergic agent.

InChI:InChI=1/C15H19ClO3/c1-15(2,14(18)19-3)12-8-6-11(7-9-12)13(17)5-4-10-16/h6-9H,4-5,10H2,1-3H3

Upstream product

• 108-86-1 bromobenzene 
• 547-63-7 Methyl isobutyrate 
• 154825-93-1 4-(4-Hydroxy-1-butynyl)-α,α-dimethylbenzeneacetic acid methyl ester 
• 162096-54-0 2-(4-cyclopropanecarbonyl-phenyl)-2-methyl-propionic acid 
• 515-40-2 neophyl chloride 
• 169280-26-6 2-(4-(1-Oxo-1-cyclopropanyl)-phenyl)-2-methylpropanol 
• 71-43-2 benzene 
• 169032-17-1 2-[4-(4-chloro-butyryl)-phenyl]-2-methyl-propionitrile 
• 169280-21-1 2-[4-(4-chloro-butyryl)-phenyl]-2-methyl-propionic acid 
• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 4559-96-0 1-(4-bromophenyl)-4-chlorobutan-1-one 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 67-56-1 methanol 
• 57625-74-8 methyl 2-methyl-2-phenylpropionate 

Downstream Products

• 83799-24-0 fexofenadine 
• 154825-96-4 fexofenadine methyl ester 
• 189064-48-0 4-[4-[4-(Hydroxydiphenylmethyl-)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetic acid methyl ester 
• 169280-25-5 2-(4-(4-Chloro-1-oxo-butyl))-phenyl-2-methylpropanol 
• 1451149-73-7 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)-1,1-dimethoxybutyl)phenyl)-2-methyl-propanoic acid 
• 1451149-72-6 methyl 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)-1,1-dimethoxybutyl)phenyl)-2-methyl-propanoate 
• 154477-55-1 methyl 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoate 
• 1451149-74-8 methyl 2-(4-(4-chloro-1,1-dimethoxybutyl)phenyl)-2-methyl-propanoate 
• 937009-94-4 methyl 3-{4-[4-(hydroxydiphenylmetyl)-1-piperidinyl]-1-oxobutyl}-α,α-dimethylbenzeneacetate 
• 169280-33-5 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-oxobutyl]-α,α-dimethylbenzeneacetic acid, methyl ester hydrochloride 
• 252022-32-5 Methyl 2-[4-(1-hydroxy-4-chlorobutyl)phenyl]isobutyrate 

Relevant articles and documents

Preparation method of fexofenadine

The invention provides a preparation method of fexofenadine, which comprises the following steps: by using bromobenzene as a raw material, carrying out Friedel-Crafts acylation reaction to obtain 4'-bromo-4-chlorophenone ; enabling 4'-bromo-4-chlorobutanone and 1-methoxy-1-(trimethylsiloxy)-2-methyl-1-propene to subjected to coupling reaction to obtain 2-[4-(4 -chloro-1-butyryl)phenyl]-2-methyl methyl propionate; and sequentially carrying out N-alkylation, carbonyl reduction and alkaline hydrolysis on 2-[4-(4 -chloro-1-butyryl)phenyl]-2-methylpropanoate to obtain fexofenadine. The method has the advantages of cheap and easily available raw materials, easiness in operation, high yield, low cost, no meta-isomer, suitability for industrial production and the like.

INTERMEDIATES USEFUL FOR THE SYNTHESIS OF FEXOFENADINE, PROCESSES FOR THEIR PREPARATION AND FOR THE PREPARATION OF FEXOFENADINE

Intermediates useful for the synthesis of fexofenadine, processes for their preparation and processes for the synthesis of fexofenadine are described.

PROCESS FOR PREPARING FEXOFENADINE

A process for preparing fexofenadine is described, comprising the purification of 4-[4-chloro-l-oxobutyl]-2,2-dimethylphenyl acetic acid alkyl ester by means of suspension in a hydrocarbon, preferably n-heptane. The compound thus obtained is dissolved in a suitable solvent and condensed with azacyclanol to give the compound shown below (I) where R is an alkyl radical, which is then hydrolysed and reduced to give fexofenadine.