2-Pyrrolidinone CAS 616-45-5
Introduction：Basic information about 2-Pyrrolidinone CAS 616-45-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
2-Pyrrolidinone Basic information
| Product Name: | 2-Pyrrolidinone |
| Synonyms: | 2-Pyrrolidone Butyrolactam;2-AZACYCLOPENTANONE;2-P;2-KETOPYRROLIDINE;ALPHA-PYRROLIDONE;PIPERIDINIC ACID LACTAM;2-Oxopyrrolidine;2-Pyrol |
| CAS: | 616-45-5 |
| MF: | C4H7NO |
| MW: | 85.1 |
| EINECS: | 210-483-1 |
| Product Categories: | Pyrrolidones;Solvent;API;616-45-5;2-P |
| Mol File: | 616-45-5.mol |
2-Pyrrolidinone Chemical Properties
| Melting point | 23-25 °C (lit.) |
| Boiling point | 245 °C (lit.) |
| density | 1.12 g/mL at 25 °C (lit.) |
| vapor density | 2.9 (vs air) |
| vapor pressure | 0.04 hPa (20 °C) |
| FEMA | 4829 | 2-PYRROLIDONE |
| refractive index | n |
| Fp | >230 °F |
| storage temp. | 2-8°C |
| solubility | H2O: miscible (completely) |
| form | Liquid |
| pka | 16.62±0.20(Predicted) |
| color | Clear colorless to pale yellow |
| PH | 9-11 (100g/l, H2O, 20℃) |
| explosive limit | 1.8-16.6%(V) |
| biological source | synthetic |
| Water Solubility | miscible |
| Sensitive | Hygroscopic |
| Merck | 14,8016 |
| BRN | 105241 |
| Stability: | Hygroscopic |
| InChI | 1S/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6) |
| InChIKey | HNJBEVLQSNELDL-UHFFFAOYSA-N |
| SMILES | O=C1CCCN1 |
| LogP | -0.71 at 20℃ |
| Surface tension | 46.31mN/m at 293.15K |
| CAS DataBase Reference | 616-45-5(CAS DataBase Reference) |
| NIST Chemistry Reference | 2-Pyrrolidinone(616-45-5) |
| EPA Substance Registry System | 2-Pyrrolidinone (616-45-5) |
Safety Information
| Risk Statements | 22 |
| Safety Statements | 24/25 |
| RIDADR | 2810 |
| WGK Germany | 1 |
| RTECS | UY5715000 |
| Autoignition Temperature | 395 °C |
| TSCA | TSCA listed |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| HS Code | 29339980 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Eye Irrit. 2 Repr. 1B |
| Hazardous Substances Data | 616-45-5(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: > 3200 mg/kg |
| 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 | 2-Pyrrolidinone is a widely used organic polar solvent for various applications. 2-Pyrrolidinone is also an intermediate in the manufacture of polymers. |
| Uses | 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 ofdehydration of 4-aminobutanoic acid. It is produced commercially by condensationof butyrolactone with ammonia, a method first described in 1936. Othersynthetic routes include carbon monoxide insertion into allylamine, hydrolytichydrogenation of succinonitrile, and hydrogenation of ammoniacal solutions ofmaleic 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, andskin. Although reported to be a skin sensitizer in animal tests, there is no indicationthat 2-pyrrolidone is a skin sensitizer in human exposures (Anon 1975). 2-Pyrrolidonehas been reported to enhance the permeability of human skin for methanol,but reduced the permeability for octanol (Southwell et al 1983). |
| Flammability and Explosibility | Non flammable |
| Pharmaceutical Applications | Pyrrolidone and N-methylpyrrolidone are mainlyused as solvents in veterinary injections. Pyrrolidone has beenshown to be a better solubilizer than glycerin, propylene glycol, orethanol. They have also been suggested for use in humanpharmaceutical formulations as solvents in parenteral, oral, andtopical applications. In topical applications, pyrrolidones appear tobe effective penetration enhancers. Pyrrolidones have also beeninvestigated for their application in controlled-release depotformulations. |
| Industrial uses | 2-Pyrrolidone is used as an intermediate for synthesis of l-vinyl-2-pyrrolidone andvarious TV-methylol derivatives used as textile-finishing agents; as a solvent forvarious polymers, chlordane and DDT, d-sorbitol, glycerin, and sugars; and as adecolorizing agent for kerosene, fatty oils, and rosins. N-methyl-2-pyrrolidone and2-pyrrolidone are utilized in petroleum refining to selectively extract aromaticsfrom paraffinic hydrocarbons. 2-Pyrrolidone is used as a plasticizer and coalescingagent 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-formingpolymer (Anon. 1975; Hort and Anderson 1978). |
| Safety | Pyrrolidones are mainly used in veterinary injections and have alsobeen suggested for use in human oral, topical, and parenteralpharmaceutical formulations. In mammalian species, pyrrolidonesare biotransformed to polar metabolites that are excreted via theurine. Pyrrolidone is mildly toxic by ingestion and subcutaneousroutes; 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 inanimals (Lundgren et al 1980). 2-Pyrrolidone has been reported to be an endogenousconstituent in the brains of mice (Callery et al 1978) and bovine (Mori et al1975). The aliphatic polyamine putrescine has been demonstrated to be metabolizedto 2-pyrrolidone in rat liver slices (Lundgren and Hankins 1978; Lundgren etal 1985) and to lesser extent by slices of spleen and lung, but not in tissue slicesfrom kidney, brain, heart, or rear leg muscle (Lundgren and Hankins 1978). Themetabolism of putrescine is catalyzed by the microsomal enzyme diamine oxidase(EC 1.4.3.6) to 4-aminobutyraldehyde, which is subsequently oxidized to theneurotransmitter 4-aminobutanoic acid (4-aminobutyric acid, GAB A) or is cyclizedto 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 carbondioxide (Bandle et al 1984). An enzyme system residing in the soluble fraction ofrabbit liver catalyzes the conversion of delta'-pyrroline to ?-aminobutyric acid andits 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 drugmethadone (Kreek 1980). |
| storage | Pyrrolidone is chemically stable and, if it is kept in unopenedoriginal containers, the shelf-life is approximately one year.Pyrrolidone should be stored in a well-closed container protectedfrom light and oxidation, at temperatures below 20°C. |
| Incompatibilities | Pyrrolidone is incompatible with oxidizing agents and strong acids. |
2-Pyrrolidinone Preparation Products And Raw materials
| Raw materials | Ammonium hydroxide-->Ammonia-->Gamma Butyrolactone-->N-Methyl-2-pyrrolidone-->1-[(6-chloropyridin-3-yl)Methyl]iMidazolidin-2-one-->2-Chloropyridine-5-carbaldehyde |
| Preparation Products | 9-VINYLANTHRACENE-->4-Aminobutyric acid-->1-(3-(4-AMINO-2,6-DICHLOROPHENOXY)PROPYL)PYRROLIDIN-2-ONE-->1-(3-Hydrazinylpropyl)pyrrolidin-2-one-->1-(3-AMINOPROPYL)-2-PYRROLIDINONE-->Aniracetam-->1,5-Diazabicyclo[4.3.0]non-5-ene-->Piracetam-->Alendronate sodium-->PYRROLIDONE HYDROTRIBROMIDE-->4-Bromo-1-butanol-->γ-Nitrobutyric acid-->6,7-DIHYDRO-2-PHENYL-5H-PYRROLO[2,1-C]-1,2,4-TRIAZOLIUM CHLORIDE-->(S)2-(2-Oxo pyrrolidin-1-yl)-Butiric acid methyl ester-->N-Octyl pyrrolidone-->1-(1-ADAMANTYL)PYRROLIDIN-2-ONE |
