155405-79-1

Basic information

• Product Name: 4-(3-Bromo-4-oxobutyl)-benzoic acid methyl ester
• CAS NO: 155405-79-1
• Molecular Formula: C₁₂H₁₃BrO₃
• Molecular Weight: 285.133789
• Mol File: 155405-79-1.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 4-(3-Bromo-4-oxobutyl)-benzoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-Bromo-4-oxobutyl)-benzoic acid methyl ester(155405-79-1)
• EPA Substance Registry System: 4-(3-Bromo-4-oxobutyl)-benzoic acid methyl ester(155405-79-1)

Safety Data

• Hazardous Substances Data: 155405-79-1(Hazardous Substances Data)

Usage

General Description

4-(3-Bromo-4-oxobutyl)-benzoic acid methyl ester is a chemical compound with the molecular formula C13H13BrO3. It is a methyl ester derivative of 4-(3-Bromo-4-oxobutyl)-benzoic acid. 4-(3-Bromo-4-oxobutyl)-benzoic acid methyl ester is primarily used as an intermediate in the synthesis of various pharmaceuticals, agrochemicals, and organic compounds. It is also utilized in research and development as a building block for more complex chemical structures. The chemical is known to possess certain biological activities and is of interest in the pharmaceutical industry for its potential medicinal properties. Additionally, it is classified as a hazardous material and should be handled and stored according to safety guidelines and regulations.

Upstream product

• 108-88-3 toluene 
• 57498-54-1 methyl 4-(4-methylphenyl)-4-oxobutanoate 
• 4619-20-9 3-(4-methylbenzoyl)propionic acid 
• 106200-41-3 4-(4-carbomethoxyphenyl)butanal 
• 619-44-3 methyl 4-iodobenzoate 
• 123910-88-3 methyl 4-(4-hydroxybut-1-yl)benzoate 
• 123910-86-1 4-(4-hydroxybut-1-ynyl)benzoic acid methyl ester 
• 619-42-1 4-methoxycarbonylphenyl bromide 

Downstream Products

• 137281-39-1 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid 
• 146943-43-3 N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester 
• 165049-28-5 N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester 4-methylbenzenesulfonic acid salt 
• 1209465-70-2 C₂₀H₁₉N₇O₅ 

Relevant articles and documents

Multi-arm polymeric prodrug conjugates of pemetrexed-based compounds

Among other aspects, provided herein are multi-arm polymeric prodrug conjugates of pemetrexed-based compounds. Methods of preparing such conjugates as well as methods of administering the conjugates are also provided. Upon administration to a patient, release of the pemetrexed-based compound is achieved.

Method for preparing pemetrexed disodium key intermediate

The invention discloses a method for preparing a pemetrexed disodium key intermediate (I). The method comprises the following steps: carrying out classical Friedenylation and esterification reactionson raw materials comprising toluene and succinic anhydride to obtain methyl 3-(4-methylphenyl)-4-oxobutanoate, carrying out oxygen or air oxidation on the methyl 3-(4-methylphenyl)-4-oxobutanoate under the catalysis of N-hydroxyphthalimide (NHPI) and cobalt acetate to obtain 4-(methoxy-4-oxobutylcarbonyl)benzoic acid, and carrying out selective reduction, selective oxidation, esterification and bromination reactions on the obtained oxidation product to prepare methyl 4-(3-bromo-4-oxobutyl)benzoate. The method has the advantages of cheap and easily available raw materials, mild reaction conditions, simplicity in treatment, good yield and good purity of the product, and suitableness for industrial production.

An Efficient Synthesis of Pemetrexed Disodium

An efficient synthetic method for the pemetrexed disodium has been developed using methyl 4-iodobenzoate and 3-buten-1-ol as starting materials via six steps. The developed process avoided some tedious workup procedures and unfriendly reagents compared with the reported synthetic routes. In addition, two impurities generated in the process were isolated and characterized by 1H NMR, 13C NMR, and HRMS. The mechanisms of the two impurities were also discussed, and the impurities could be easily removed by suitable workup procedures. The overall yield of pemetrexed disodium was increased from 12.8% (literature) to 34.9%. Therefore, this cost-effective, environmental friendly, and high-yielding process is more suitable for scale-up production of pemetrexed disodium.