106200-41-3

Basic information

• Product Name: Methyl 4-(4-oxobutyl)benzoate
• Synonyms: Methyl 4-(4-oxobutyl)benzoate;4-(4-Oxobutyl)benzoic acid methyl ester;4-(4-CARBOMETHOXYPHENYL)BUTANAL(WXG01250)
• CAS NO: 106200-41-3
• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.23776
• EINECS: 1592732-453-0
• Mol File: 106200-41-3.mol
• Article Data: 22

Chemical Properties

• Melting Point: 76.5-78 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 131 °C(Press: <1 Torr)
• Appearance: /
• Density: 1.082±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: Methyl 4-(4-oxobutyl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-(4-oxobutyl)benzoate(106200-41-3)
• EPA Substance Registry System: Methyl 4-(4-oxobutyl)benzoate(106200-41-3)

Safety Data

• Hazardous Substances Data: 106200-41-3(Hazardous Substances Data)

Usage

Description

Methyl 4-(4-oxobutyl)benzoate, also known as 4-(4-oxobutyl)benzoic Acid Methyl Ester, is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceuticals. It is characterized by its ester functional group and a butyl chain with a carbonyl group, which contributes to its reactivity and utility in chemical reactions.

Uses

Used in Pharmaceutical Industry:
Methyl 4-(4-oxobutyl)benzoate is used as a reagent for the preparation of Pemetrexed (P219500), an antifolate and nitric oxide donor. It plays a vital role in the development of anticancer agents, specifically targeting enzymes involved in nucleotide synthesis, thereby inhibiting tumor growth and progression.
Additionally, Methyl 4-(4-oxobutyl)benzoate is utilized in the synthesis of furoxanoxyalkyl esters of Pemetrexed, which are also employed as anticancer agents. These compounds exhibit enhanced activity against cancer cells by combining the antifolate properties of Pemetrexed with the nitric oxide donor capabilities of the furoxanoxyalkyl group, leading to a more effective treatment option for various types of cancer.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 23, p. 1, 1986 DOI: 10.1002/jhet.5570230101

Upstream product

• 123910-88-3 methyl 4-(4-hydroxybut-1-yl)benzoate 
• 155405-82-6 1-methoxy-4-p-carbomethoxyphenyl-1-butene 
• 615581-18-5 methyl 4-[3-(1,3-dioxolan-2-yl)propyl]benzoate 
• 123910-86-1 4-(4-hydroxybut-1-ynyl)benzoic acid methyl ester 
• 86608-70-0 2-(1,3-dioxolan-2-yl)ethyl(triphenyl)phosphonium bromide 
• 667909-36-6 4-((E)-3-[1,3]Dioxolan-2-yl-propenyl)-benzoic acid methyl ester 
• 272779-19-8 4-((E)-4-Methoxy-but-3-enyl)-benzoic acid 
• 99-94-5 p-Toluic acid 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 627-27-0 homoalylic alcohol 
• 6108-17-4 lithium acetate dihydrate 
• 60-29-7 diethyl ether 
• 927-74-2 3-Butyn-1-ol 
• 619-44-3 methyl 4-iodobenzoate 

Downstream Products

• 106200-42-4 piperidine enamine of 4-p-carbomethoxyphenylbutyraldehyde 
• 123910-83-8 Methyl 4-(5,5-dicyano-4-pentenyl)benzoate 
• 229471-26-5 4-(4-hydroxy-5-nitropentyl)benzoic acid methyl ester 
• 103094-76-4 methyl 4-(4-hydroxypentyl)benzoate 
• 615581-20-9 methyl 4-(4-hydroxy-5-phenylpentyl)benzoate 
• 615581-19-6 methyl 4-(4-hydroxyhexyl)benzoate 
• 615581-21-0 methyl 4-(4-hydroxy-5-methylhexyl)benzoate 
• 134373-15-2 4-<2-(2,4-diamino-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoic acid 
• 144051-63-8 4-[3-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoic acid 
• 125991-54-0 diethyl N-<4-<3-(2-amino-4(3H)-oxo-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoyl>-L-glutamate 
• 259145-26-1 4-[4-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-5-nitropentyl]benzoic acid methyl ester 
• 229471-28-7 4-[5-nitro-4-(2,4,6-triaminopyrimidin-5-yl)pentyl]benzoic acid methyl ester 
• 103094-70-8 methyl 4-(4-oxopentyl)benzoate 
• 439286-28-9 methyl 4-(4-oxohexyl)benzoate 

Relevant articles and documents

A practical synthesis of multitargeted antifolate LY231514

A concise and scalable synthesis of LY231514 (1), a new pyrrolo[2,3-d]pyrimidine-based antitumor agent, is presented. Reaction of 2-bromo-4-arylbutanal 9 with 2,4-diamino-6-hydroxypyrimidinc (10) regioselectively provided pyrrolo[2,3-d]pyrimidine 11, representing the core structure of the drug, in good yield. Assimilation of the glutamic acid residue by conventional means completed the synthesis. Development of the optimized synthetic route emphasized avoiding isolation of the relatively unstable aldehyde and bromoaldehyde intermediates.

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.

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.

Synthetic pemedolac preparation process

The invention discloses a synthetic pemedolac preparation method, which specifically comprises: carrying out a Heck reaction by using methyl p-bromobenzoate and 3-butene-1-ol as starting raw materialsto obtain crude aldehyde, and directly carrying out a bromination reaction, a cyclization reaction and a hydrolysis reaction through a one-pot method to obtain pemedolac. According to the present invention, the method has characteristics of mild reaction conditions, easy control, simple and safe process operation, good product yield and high product purity.