15438-71-8

Basic information

• Product Name: (HYDROXYMETHYL)-2-PYRROLIDINONE
• Synonyms: N-HYDROXYMETHYL PYRROLIDONE;1-(HYDROXYMETHYL)PYRROLIDIN-2-ONE;METHYLOLPYRROLIDONE;IFLAB-BB F0861-0038;(HYDROXYMETHYL)-2-PYRROLIDINONE;1-(Hydroxymethyl)-2-pyrrolizinone;1-Hydroxymethyl-2-pyrrolidone;1-Hydroxymethyl-2-pyrrolidinone
• CAS NO: 15438-71-8
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.13
• EINECS: 239-451-5
• Mol File: 15438-71-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 77-79.5 °C
• Boiling Point: 291.1 °C at 760 mmHg
• Flash Point: 129.9 °C
• Appearance: /
• Density: 1.213 g/cm³
• Vapor Pressure: 0.000215mmHg at 25°C
• Refractive Index: 1.51
• PKA: 13.41±0.10(Predicted)
• CAS DataBase Reference: (HYDROXYMETHYL)-2-PYRROLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (HYDROXYMETHYL)-2-PYRROLIDINONE(15438-71-8)
• EPA Substance Registry System: (HYDROXYMETHYL)-2-PYRROLIDINONE(15438-71-8)

Safety Data

• Hazardous Substances Data: 15438-71-8(Hazardous Substances Data)

Usage

General Description

(HYDROXYMETHYL)-2-PYRROLIDINONE is a chemical compound with the molecular formula C5H9NO2. It is a derivative of 2-pyrrolidinone and is characterized by the presence of a hydroxymethyl group. (HYDROXYMETHYL)-2-PYRROLIDINONE is commonly used as a solvent or co-solvent in various industrial applications, including coatings, adhesives, and pharmaceuticals. It is known for its high solvency power and low volatility, making it suitable for use in a wide range of formulations. In addition to its solvent properties, (HYDROXYMETHYL)-2-PYRROLIDINONE also exhibits hygroscopic and chelating properties, making it a versatile and useful chemical in various industries.

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

Upstream product

• 6859-99-0 3-hydroxypiperazine 
• 616-45-5 2-pyrrolidinon 
• 56145-24-5 methyl 2-methyl-5-oxopyrrolidine-2-carboxylate 
• 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

• 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 
• 109071-38-7 1-(acetoxymethyl)-2-pyrrolidinone 
• 82176-02-1 N-tert-butoxycarbonyl-S-<(2-oxo-1-pyrrolidinyl)methyl>-L-cysteine p-nitrophenyl ester 

Relevant articles and documents

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.

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.

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.

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).