925-57-5

Basic information

• Product Name: 4-Hydroxybutanoic acid methyl ester
• Synonyms: 4-Hydroxybutanoic acid methyl ester;4-Hydroxybutyric acid methyl ester;Butanoic acid, 4-hydroxy-, Methyl ester
• CAS NO: 925-57-5
• Molecular Formula: C₅H₁₀O₃
• Molecular Weight: 118.13
• Mol File: 925-57-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 190.872 °C at 760 mmHg
• Flash Point: 77.376 °C
• Appearance: /
• Density: 1.054 g/cm³
• Vapor Pressure: 0.143mmHg at 25°C
• Refractive Index: 1.422
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 14.68±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 4-Hydroxybutanoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxybutanoic acid methyl ester(925-57-5)
• EPA Substance Registry System: 4-Hydroxybutanoic acid methyl ester(925-57-5)

Safety Data

• Hazardous Substances Data: 925-57-5(Hazardous Substances Data)

Usage

Description

4-Hydroxybutanoic acid methyl ester, also known as 4-Hydroxybutyric Acid Methyl Ester, is a chemical compound derived from 4-Hydroxybutyric Acid (H833015). It is characterized by its clear oil chemical property.

Uses

Used in Pharmaceutical Industry:
4-Hydroxybutanoic acid methyl ester is used as a reactant for the preparation of 4-aminothiazolyl analogs of natural product GE2270 A. 4-Hydroxybutanoic acid methyl ester is particularly useful against Clostridium difficile infection, a significant concern in healthcare settings.
Used in Chemical Synthesis:
4-Hydroxybutanoic acid methyl ester is utilized as a key intermediate in the synthesis of various organic compounds, contributing to the development of new pharmaceuticals and other chemical products.

InChI:InChI=1/C5H10O3/c1-8-5(7)3-2-4-6/h6H,2-4H2,1H3

Upstream product

• 73510-05-1 dimethoxytetrahydrofuran 
• 13192-04-6 dimethyl 2-ketoglutarate 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 616-45-5 2-pyrrolidinon 
• 67-56-1 methanol 
• 110-63-4 Butane-1,4-diol 
• 96-48-0 4-butanolide 
• 3251-07-8 methyl 4-aminobutyrate 
• 591-81-1 4-hydroxybutanoic acid 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 

Downstream Products

• 495390-31-3 3-(methoxycarbonyl)propyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 960062-15-1 C₅₃H₅₃N₁₃O₁₁S₆ 
• 1148129-34-3 cis-4-{(3,5-bis(trifluoromethyl)benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2,6-diethylpiperidine-1-carboxylic acid 3-methoxycarbonyl-propyl ester 
• 1160960-62-2 C₅₈H₆₁N₁₃O₁₃S₆ 
• 202402-03-7 4-hydroxy-N-(1-phenylethyl)butanamide 
• 19340-88-6 N-benzyl-4-hydroxybutanamide 
• 14273-85-9 methyl 4-iodobutanoate 
• 927-60-6 hydroxymethyl propionamide 
• 13865-19-5 4-oxobutanoic acid methyl ester 
• 96-48-0 4-butanolide 
• 29107-82-2 methyl 4-(phenylsulfonyl)butanoate 

Relevant articles and documents

Gold-nanoparticle-based catalysts for the oxidative esterification of 1,4-butanediol into dimethyl succinate

The oxidation of 1,4-butanediol and butyrolactone have been investigated by using supported gold, palladium and gold-palladium nanoparticles. The products of such reactions are valuable chemical intermediates and, for example, can present a viable pathway for the sustainable production of polymers. If both gold and palladium were present, a significant synergistic effect on the selective formation of dimethyl succinate was observed. The support played a significant role in the reaction, with magnesium hydroxide leading to the highest yield of dimethyl succinate. Based on structural characterisation of the fresh and used catalysts, it was determined that small gold-palladium nanoalloys supported on a basic Mg(OH)2 support provided the best catalysts for this reaction. Twice as nice: The oxidation of 1,4-butanediol and butyrolactone has been investigated over supported gold, palladium and gold-palladium nanoparticles. The oxidation of both hydroxyl groups of α,γ-diols has previously proved to be difficult. Small AuPd alloy nanoparticles on a basic Mg(OH)2 support provide the best catalysts for this reaction. Copyright

Synthesis of biobased N-methylpyrrolidone by one-pot cyclization and methylation of γ-aminobutyric acid

N-Methylpyrrolidone (NMP) is an industrial solvent that is currently based on fossil resources. In order to prepare it in a biobased way, the possibility to synthesize NMP from γ-aminobutyric acid (GABA) was investigated, since GABA can be obtained from glutamic acid, an amino acid that is present in many plant proteins. Cyclization of GABA to 2-pyrrolidone and subsequent methylation of 2-pyrrolidone to NMP was achieved in a one-pot procedure, using methanol as the methylating agent and a halogen salt (i.e. ammonium bromide) as a catalyst. A selectivity above 90% was achieved, as well as a high conversion. Methylation of 2-pyrrolidone could also be done with dimethyl carbonate, but then the selectivity for NMP was less (67%).

Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates

Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic γ-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products.