15438-71-8

Usage

Uses

Used in Coatings Industry:
(HYDROXYMETHYL)-2-PYRROLIDINONE is used as a solvent or co-solvent for its exceptional solvency power and low volatility, which are crucial for the performance and drying properties of coatings. Its hygroscopic and chelating properties also contribute to the stability and quality of the final product.
Used in Adhesives Industry:
In the adhesives industry, (HYDROXYMETHYL)-2-PYRROLIDINONE serves as a solvent or co-solvent, enhancing the adhesive's bonding strength and workability. Its ability to dissolve a wide range of substances and its low volatility make it an ideal component for formulating high-performance adhesives.
Used in Pharmaceuticals Industry:
(HYDROXYMETHYL)-2-PYRROLIDINONE is utilized as a solvent or co-solvent in the pharmaceutical sector due to its capacity to dissolve various active pharmaceutical ingredients (APIs) and excipients. Its hygroscopic and chelating properties also play a role in stabilizing formulations and improving the overall performance of pharmaceutical products.
Used in Other Industrial Applications:
Beyond the aforementioned industries, (HYDROXYMETHYL)-2-PYRROLIDINONE's versatility extends to other applications where its solvency, hygroscopic, and chelating properties are advantageous. Its low volatility ensures that it can be used in environments where evaporation is a concern, while its ability to form complexes with metal ions can be beneficial in various chemical processes.

InChI:InChI=1/C5H9NO2/c7-4-6-3-1-2-5(6)8/h7H,1-4H2

Upstream product

• 56145-24-5 methyl 2-methyl-5-oxopyrrolidine-2-carboxylate 
• 616-45-5 2-pyrrolidinon 
• 6859-99-0 3-hydroxypiperazine 
• 62351-29-5 (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-oxo-pyrrolidin-1-ylmethyl ester 
• 56-23-5 tetrachloromethane 
• 50-00-0 formaldehyd 
• 7732-18-5 water 

Downstream Products

• 109071-38-7 1-(acetoxymethyl)-2-pyrrolidinone 
• 129084-60-2 Z(OMe)-Cys(Pym)-OH*DCHA 
• 129111-69-9 Boc-Cys(Pym)-OH*DCHA 
• 34577-76-9 N-phenoxymethyl-2-pyrrolidinone 
• 93287-12-8 1-(bromomethyl)-2-pyrrolidinone 
• 82176-02-1 N-tert-butoxycarbonyl-S-<(2-oxo-1-pyrrolidinyl)methyl>-L-cysteine p-nitrophenyl ester 

Relevant academic research and scientific papers

SOLID-PHASE COSOLVENTS. A POLYMER ANALOG OF N-METHYL-2-PYRROLIDONE BASED ON CROSSLINKED POLYSTYRENE

Polymer analogs of N-methyl-2-pyrrolidone were prepared by reacting crosslinked polystyrene with N-hydroxymethyl-2-pyrrolidone.These polymers are effective catalysts of nucleophilic substitution reactions carried out under liquid-solid (L-S) and liquid-solid-liquid conditions.

Oxidation of 3-hydroxypiperidines with iodosylbenzene in water: Tandem oxidative grob fragmentation-cyclization reaction

Oxidation of 3-hydroxypiperidine with iodosylbenzene in water afforded 2-pyrrolidinone directly in good yields. The reaction probably involves oxidative Grob fragmentation yielding imino aldehyde, which upon hydrolysis produces 2-pyrrolidinone via a cyclization-oxidation sequence.

Acyloxymethyl as a drug protecting group. Part 3. Tertiary O-amidomethyl esters of penicillin G: Chemical hydrolysis and anti-bacterial activity

Purpose. O-(N-alkylamido)methyl esters of penicillin G were studied as a new class of prodrugs. Methods. Their hydrolysis in aqueous buffers containing 20% (v/v) of acetonitrile was investigated by HPLC. Results. A U-shaped pH-rate profile was seen with a pH-independent process extending from pH ca. 2 to pH ca. 10. This pathway is characterised by kinetic data that are consistent with a unimolecular mechanism involving rate-limiting iminium ion formation and penicillinoate expulsion. Penicillin G and the corresponding amide are the ultimate products detected and isolated, indicating that p-lactam ring opening is much slower than ester hydrolysis. The O-(N-alkylamido)methyl esters of penicillin G displayed similar in vitro antibacterial activity to penicillin G itself. Conclusions. Compared to the penicillin G derivatives, the much higher stability of the O-(N-methylbenzamido)methyl benzoate, acetate and valproate esters (which gave rise to a Bronsted β(1g) value of ca. -1) suggests that tertiary N-acyloxymethylamides may be useful prodrugs for carboxylic acid drugs with pK(a) > 4.

Preparation, properties, and antibacterial behavior of a novel cellulose derivative containing Lactam groups

Lactam groups were introduced onto the backbone of hydroxyethyl cellulose (HEC) to modify properties, such as solubility in organic solvents and solution viscosity and to introduce possible antibacterial activity. Functionalization was achieved using 1-(hydroxymethyl)-2-pyrrolidinone (HMP), and the functionalization reactions were investigated using NMR spectroscopy. The covalent attachment between HEC and HMP was confirmed using 1H-13C correlated NMR experiments. Degrees of functionalization were calculated using integrated 12C NMR spectra, with values of up to 0.9 being demonstrated on the primary alcohol functionality of HEC. The functionalized HECs showed markedly different properties to unfunctionalized HEC, including the ability to swell considerably in water. Functionalized HEC displayed increased thermal stability and reduced solution viscosity compared with unfunctionalized HEC. Moreover, functionalization altered the bacterial adhesion characteristics compared with unfunctionalized HEC.

CARBON DIOXIDE CO-FLUID

A carbon dioxide/co-fluid mixture is provided for use in a refrigeration cycle in which the carbon dioxide is alternately absorbed and desorbed from the co-fluid. Suitable co-fluids are selected from the class of alkoxylated carboxylic amides, wherein the amides are cyclic or non-cyclic. It has been discovered that N-2,5,8,11-tetraoxadodecyl-2-pyrrolidinone and its homologs exhibit an advantageous property of a high rate of desorption at lower temperatures.

Highly efficient synthetic method on pyroacm resin using the boc SPPS protocol for C-terminal cysteine peptide synthesis

A very effective process on Pyroacm resin was developed for solid-phase peptide synthesis (SPPS) of C-terminal cysteine and cysteine ester peptides. The process uses cysteine side chain anchoring to the Pyroacm resin and the Boc protocol for SPPS. The Pyroacm resin showed remarkable stability under standard trifluoromethanesulfonic acid (TFMSA) cleavage condition. TFMSA cleavage of protecting groups generates a peptide-linked resin, which can be subjected to peptide modification reactions. Finally, the peptide can be cleaved from the resin using methoxycarbonylsulfenyl chloride. The utility of this protocol was demonstrated by its applications to the synthesis of model peptides, key intermediates in the preparation of natural products riparin 1.2 and a-factor.

Pyroacm Resin: An Acetamidomethyl Derived Resin for Solid Phase Synthesis of Peptides through Side Chain Anchoring of C-Terminal Cysteine Residues

The design, synthesis and utilization of an efficient acetamidomethyl derived resin for the peptide synthesis is presented using established Fmoc and Boc protocols via side chain anchoring. Cleavage of the target peptide from the resin is performed using carboxymethylsulfenyl chloride under mild conditions which gave in situ thiol-sulfenyl protection of the cysteine residues. The utility of the resin is successfully demonstrated through applications to the syntheses of model peptides and natural products Riparin 1.1 and Riparin 1.2. (Chemical Equation Presented).

Preparation, properties, and antibacterial behavior of a novel cellulose derivative containing lactam groups

Lactam groups were introduced onto the backbone of hydroxyethyl cellulose (HEC) to modify properties, such as solubility in organic solvents and solution viscosity and to introduce possible antibacterial activity. Functionalization was achieved using 1-(hydroxymethyl)-2-pyrrolidinone (HMP), and the functionalization reactions were investigated using NMR spectroscopy. The covalent attachment between HEC and HMP was confirmed using 1H-13C correlated NMR experiments. Degrees of functionalization were calculated using integrated 13C NMR spectra, with values of up to 0.9 being demonstrated on the primary alcohol functionality of HEC. The functionalized HECs showed markedly different properties to unfunctionalized HEC, including the ability to swell considerably in water. Functionalized HEC displayed increased thermal stability and reduced solution viscosity compared with unfunctionalized HEC. Moreover, functionalization altered the bacterial adhesion characteristics compared with unfunctionalized HEC.

Antimicrobial Haloalkyl Heterocycle Compounds

This application describes compounds useful as anti-microbial agents, including as antibacterial, disinfectant, antifungal, germicidal or antiviral agents.

A simple and efficient preparation of novel formaldehyde derivatives

New formaldehyde derivatives were prepared in good yields by a short and versatile route. Several crystal structures of corresponding thioacetic acid esters and thiols were determined. The thioacetates were cleaved under acidic or basic conditions affording the thiols in high yield, thus introducing the new substance classes of N-mercaptomethyl-alkylcarboxamides, N-mercapto- methylsulfonamides, and alkoxymethanethiols. Georg Thieme Verlag Stuttgart New York.