616-45-5 Usage
Chemical Properties
2-Pyrrolidinone occurs as a colorless or slightly grayish liquid, as white or almost white crystals, or colorless crystal needles. It has a characteristic odor. miscible with water, alcohol, ether, chloroform, benzene, ethyl acetate and carbon disulfide, insoluble in petroleum ether.
Uses
Different sources of media describe the Uses of 616-45-5 differently. You can refer to the following data:
1. 2-Pyrrolidinone is a widely used organic polar solvent for various applications. 2-Pyrrolidinone is also an intermediate in the manufacture of polymers.
2. 2-pyrrolidone widely exists in various physiologically active natural products in nature. For example, it is the main structural unit of gonadotropin releasing hormone. At the same time, 2-pyrrolidone is an important raw material and intermediate of medicine, pesticide, dye, peptide and other chemicals. If it is used as the end chain of peptide, it also plays a stable role in the conformation of the compound. Many polysubstituted 2-pyrrolidones have been used in the synthesis and production of a variety of drugs and applied for patents.
Preparation
Pyrrolidone is prepared from butyrolactone by a Reppe process, in which acetylene is reacted with formaldehyde.
Definition
ChEBI: 2-Pyrrolidinone is the simplest member of the class of pyrrolidin-2-ones, consisting of pyrrolidine in which the hydrogens at position 2 are replaced by an oxo group. The lactam arising by the formal intramolecular condensation of the amino and carboxy groups of gamma-aminobutyric acid (GABA). It has a role as a polar solvent and a metabolite.
Production Methods
The synthesis of 2-pyrrolidone was first reported in 1889 as the product of
dehydration of 4-aminobutanoic acid. It is produced commercially by condensation
of butyrolactone with ammonia, a method first described in 1936. Other
synthetic routes include carbon monoxide insertion into allylamine, hydrolytic
hydrogenation of succinonitrile, and hydrogenation of ammoniacal solutions of
maleic and succinnic acids (Hort and Anderson 1978).
Reactions
2-Pyrrolidone undergoes the reactions of a typical lactam, e.g. ring opening, attack on the carbonyl group, and replacement of hydrogens alpha to the carbonyl group. Strong acids and bases catalyze the hydrolysis of 2-pyrrolidone to 4-aminobutanoic acid (GABA). The hydrogen atom on the nitrogen atom is easily replaced by alkylation reactions with alkyl halide or sulfates, or reaction with acid anhydrides, acyl halides, ethylene oxide, and styrene. Condensation reactions with secondary amines and alcohols, and O-alkylation reactions occur at the carbonyl group. In the presence of anionic catalyst systems, 2-pyrrolidone is polymerized to polypyrrolidone, nylon-4 (Hort and Anderson 1978).
Health Hazard
Exposure to 2-pyrrolidone produces irritation to the eyes, mucous membranes, and
skin. Although reported to be a skin sensitizer in animal tests, there is no indication
that 2-pyrrolidone is a skin sensitizer in human exposures (Anon 1975). 2-Pyrrolidone
has been reported to enhance the permeability of human skin for methanol,
but reduced the permeability for octanol (Southwell et al 1983).
Flammability and Explosibility
Nonflammable
Pharmaceutical Applications
Pyrrolidone and N-methylpyrrolidone are mainly
used as solvents in veterinary injections. Pyrrolidone has been
shown to be a better solubilizer than glycerin, propylene glycol, or
ethanol. They have also been suggested for use in human
pharmaceutical formulations as solvents in parenteral, oral, and
topical applications. In topical applications, pyrrolidones appear to
be effective penetration enhancers. Pyrrolidones have also been
investigated for their application in controlled-release depot
formulations.
Industrial uses
2-Pyrrolidone is used as an intermediate for synthesis of l-vinyl-2-pyrrolidone and
various TV-methylol derivatives used as textile-finishing agents; as a solvent for
various polymers, chlordane and DDT, d-sorbitol, glycerin, and sugars; and as a
decolorizing agent for kerosene, fatty oils, and rosins. N-methyl-2-pyrrolidone and
2-pyrrolidone are utilized in petroleum refining to selectively extract aromatics
from paraffinic hydrocarbons. 2-Pyrrolidone is used as a plasticizer and coalescing
agent for acrylic latices and acrylic/styrene copolymers in emulsion coatings, i.e.
floor waxes. A linear high molecular weight polyamide polymer of 2-pyrrolidone,
nylon-4, is used as a textile fiber, injection molding compound, and film-forming
polymer (Anon. 1975; Hort and Anderson 1978).
Safety
Pyrrolidones are mainly used in veterinary injections and have also
been suggested for use in human oral, topical, and parenteral
pharmaceutical formulations. In mammalian species, pyrrolidones
are biotransformed to polar metabolites that are excreted via the
urine. Pyrrolidone is mildly toxic by ingestion and subcutaneous
routes; mutagenicity data have been reported.
LD50 (guinea pig, oral): 6.5 g/kg
LD50 (rat, oral): 6.5 g/kg
Metabolism
A metabolite of 2-pyrrolidone, 4-aminobutanoic acid has been identified in
animals (Lundgren et al 1980). 2-Pyrrolidone has been reported to be an endogenous
constituent in the brains of mice (Callery et al 1978) and bovine (Mori et al
1975). The aliphatic polyamine putrescine has been demonstrated to be metabolized
to 2-pyrrolidone in rat liver slices (Lundgren and Hankins 1978; Lundgren et
al 1985) and to lesser extent by slices of spleen and lung, but not in tissue slices
from kidney, brain, heart, or rear leg muscle (Lundgren and Hankins 1978). The
metabolism of putrescine is catalyzed by the microsomal enzyme diamine oxidase
(EC 1.4.3.6) to 4-aminobutyraldehyde, which is subsequently oxidized to the
neurotransmitter 4-aminobutanoic acid (4-aminobutyric acid, GAB A) or is cyclized
to delta1-pyrroline (Seiler 1980; Lundgren et al 1980; Callery et al 1980),
which is in turn oxidized to 5-hydroxy-2-pyrrolidone (Lundgren and Fales 1980).
There is evidence that 5-hydroxy-2-pyrrolidone is further metabolized to succinimide,
malimide, 2- and 3-hydroxysuccinamic acids, maleamic acid, and carbon
dioxide (Bandle et al 1984). An enzyme system residing in the soluble fraction of
rabbit liver catalyzes the conversion of delta'-pyrroline to ?-aminobutyric acid and
its lactam, 2-pyrrolidone (Callery et al 1982). 2-Pyrrolidone has been identified as a urinary metabolite of N-nitrosopyrrolidine (Cottrell et al 1980) and the drug
methadone (Kreek 1980).
storage
Pyrrolidone is chemically stable and, if it is kept in unopened
original containers, the shelf-life is approximately one year.
Pyrrolidone should be stored in a well-closed container protected
from light and oxidation, at temperatures below 20°C.
Incompatibilities
Pyrrolidone is incompatible with oxidizing agents and strong acids.
Check Digit Verification of cas no
The CAS Registry Mumber 616-45-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 6 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 616-45:
(5*6)+(4*1)+(3*6)+(2*4)+(1*5)=65
65 % 10 = 5
So 616-45-5 is a valid CAS Registry Number.
InChI:InChI=1/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6)
616-45-5Relevant articles and documents
Comments on 'Unusual oxidative rearrangement of 1,5-diazadecalin'
Winkler, Tammo
, p. 2051 - 2052 (2004)
Oxidation of cis or trans 1,5-diazadecalin with (PhIO)n yields 2-pyrrolidinone and not 1,6-diaza-2,7-cyclodecadione, as reported. This is shown by a comparison of the NMR data of the reaction product with those of 2-pyrrolidinone and 1,6-diaza-2,7-cyclodecadione.
-
Jaz,Darreux
, p. 277 (1966)
-
One-Step Conversion of Glutamic Acid into 2-Pyrrolidone on a Supported Ru Catalyst in a Hydrogen Atmosphere: Remarkable Effect of CO Activation
Suganuma, Satoshi,Otani, Akihiro,Joka, Shota,Asako, Hiroki,Takagi, Rika,Tsuji, Etsushi,Katada, Naonobu
, p. 1381 - 1389 (2019)
Glutamic acid, an abundant nonessential amino acid, was converted into 2-pyrrolidone in the presence of a supported Ru catalyst under a pressurized hydrogen atmosphere. This reaction pathway proceeded through the dehydration of glutamic acid into pyroglutamic acid, subsequent hydrogenation, and the dehydrogenation–decarbonylation of pyroglutaminol into 2-pyrrolidone. In the conversion of pyroglutaminol, Ru/Al2O3 exhibited notably higher activity than supported Pt, Pd, and Rh catalysts. IR analysis revealed that Ru can hydrogenate the formed CO through dehydrogenation–decarbonylation of hydroxymethyl groups in pyroglutaminol and can also easily desorb CH4 from the active sites on Ru. Furthermore, Ru/Al2O3 showed the highest catalytic activity among the tested catalysts in the conversion of pyroglutamic acid. Consequently, the conversion of glutamic acid produced a high yield of 2-pyrrolidone by using the supported Ru catalyst. This is the first report of this one-pot reaction under mild reaction conditions (433 K, 2 MPa H2)? which avoids the degradation of unstable amino acids above 473 K.
An Isolable Terminal Imido Complex of Palladium and Catalytic Implications
Grünwald, Annette,Orth, Nicole,Scheurer, Andreas,Heinemann, Frank W.,P?thig, Alexander,Munz, Dominik
, p. 16228 - 16232 (2018)
Herein, we report the isolation and a reactivity study of the first example of an elusive palladium(II) terminal imido complex. This scaffold is an alleged key intermediate for various catalytic processes, including the amination of C?H bonds. We demonstrate facile nitrene transfer with H?H, C?H, N?H, and O?H bonds and elucidate its role in catalysis. The high reactivity is due to the population of the antibonding highest occupied molecular orbital (HOMO), which results in unique charge separation within the closed-shell imido functionality. Hence, N atom transfer is not necessarily associated with the high valency of the metal (PdIII, PdIV) or the open-shell character of a nitrene as commonly inferred.
Thermal desorption of covalently bound fullerene C60 from poly-N-vinylpyrrolidone films
Pozdnyakov,Melenevskaya,Ratnikova,Ginzburg
, p. 1965 - 1970 (2003)
Kinetics of formation of thermolysis products in heating of thin films of poly-N-vinylpyrrolidone and of poly-N-vinylpyrrolidone with covalently bound fullerene C60 was studied by thermal desorption mass spectrometry.
Inhibitors of SARM1
-
, (2022/03/02)
The present disclosure provides compounds and methods useful for inhibiting SARM1 and/or treating and/or preventing axonal degeneration.
En Route to a Heterogeneous Catalytic Direct Peptide Bond Formation by Zr-Based Metal-Organic Framework Catalysts
Conic, Dragan,De Azambuja, Francisco,Harvey, Jeremy N.,Loosen, Alexandra,Parac-Vogt, Tatjana N.,Van Den Besselaar, Maxime
, p. 7647 - 7658 (2021/06/30)
Peptide bond formation is a challenging, environmentally and economically demanding transformation. Catalysis is key to circumvent current bottlenecks. To date, many homogeneous catalysts able to provide synthetically useful methods have been developed, while heterogeneous catalysts remain largely restricted to the studies addressing the prebiotic formation of peptides. Here, the catalytic activity of Zr6-based metal-organic frameworks (Zr-MOFs) toward peptide bond formation is investigated using dipeptide cyclization as a model reaction. Unlike previous catalysts, Zr-MOFs largely tolerate water, and reactions are carried out under ambient conditions. Notably, the catalyst is recyclable and no additives to activate the COOH group are necessary, which are common limitations of previous methods. In addition, a broad reaction scope tolerates substrates with bulky and Lewis basic groups. The reaction mechanism was assessed by detailed mechanistic and computational studies and features a Lewis acid activation of carboxylate groups by Zr centers toward amine addition in which an alkoxy ligand on adjacent Zr sites assists in lowering the barrier of key proton transfers. The proposed concepts were also used to study the formation of intermolecular peptide bond formation. While intrinsic challenges associated with the catalyst structure and water removal limit a more general intermolecular reaction scope under current conditions, the results suggest that further design of Zr-MOF catalysts could render these materials broadly useful as heterogeneous catalysts for this challenging transformation.