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三臭化水素酸ピロリドン

2-Pyrrolidone

HCID 12025
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
22580-55-8
標準SMILES
O=C1CCCN1
InChIKey
HNJBEVLQSNELDL-UHFFFAOYSA-N
分子式
C4H7NO
平均分子量
85.1 g/mol
単同位体質量
85.05276385

概要

Pyrrolidin-2-one 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 metabolite and a polar solvent.

名称と識別子

優先名称
2-Pyrrolidone
IUPAC
pyrrolidin-2-one
現地名
三臭化水素酸ピロリドン
英語名
Pyrrolidone hydrotribromide
分子式
C4H8Br3NO
分子量
325.83

名称と別名

2-Pyrrolidinonepyrrolidin-2-one616-45-52-PYRROLIDONEPyrrolidoneButyrolactam2-Oxopyrrolidine2-Ketopyrrolidine2-PyrolPyrrolidongamma-Butyrolactamalpha-Pyrrolidinone
名称をさらに表示
三臭化水素酸ピロリドンピロリドン 三臭化水素酸塩2-ピロリジノン/臭化水素/臭素分子,(3:1:1)PHTSKL178YRROLIDONE HYDROTRIBROMIDEPyrrolidone hydrotribromidePYRROLIDINONE HYDROTRIBROMIDETripyrrolidone HydrotribromidePHT~Pyrrolidone hydrotribromide2-PYRROLIDINONE HYDROTRIBROMIDEPyrrolidone hydrotribromide(3:1)Pyrrolidone hydrotribromide ,97%
4-Aminobutyric acid lactamgamma-Aminobutyric lactamgamma-Aminobutyrolactamalpha-Pyrrolidonegamma-Aminobutyric acid lactamButanoic acid, 4-amino-, lactamDTXSID8027246KKL5D39EOL

データベース識別子

CAS
22580-55-8、616-45-5
PubChem CID
12025
DTXSID
DTXSID8027246
ChEMBL
CHEMBL276849
ChEBI
CHEBI:36592
UNII
KKL5D39EOL
EC Number
210-483-1
Nikkaji
J1.663B

物性

構造計算による物性

XLogP
-0.8
極性表面積
29.1 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
0
重原子数
6
形式電荷
0
複雑度
69.9

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds
SpringerMaterials PropertiesBoiling point
LogP · 3 件

log Kow= -0.85

-0.85

-0.85

Density · 3 件

1.116 @ 25 °C

Relative density (water = 1): 1.1

1.116 @25 °C

Viscosity13.3 CP @ 25 °C
Color/Form · 2 件

CRYSTALS FROM COLD PETROLEUM ETHER

Light yellow liquid

Solubility · 4 件

Very sol in alcohol, ether, benzene, chloroform, carbon disulfide

Infinitely soluble in water

1000 mg/mL at 20 °C

Solubility in water: good

CorrosivityNon-corrosive
Flash Point · 2 件

265 °F (129 °C) (open cup)

129 °C o.c.

Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 21.1% (116 of 551) of reports.

Danger

H315 (17.4%): Causes skin irritation [Warning Skin corrosion/irritation]

P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 551 reports by companies from 30 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

危険有害性情報

Regulatory Information · 4 件

Chemical: 2-Pyrrolidinone

2-Pyrrolidinone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Pyrrolidinone are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: 2-pyrrolidone (EC: 210-483-1)

2-Pyrrolidinone: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 2-Pyrrolidinone: Environment tier I assessment
Fire HazardsCombustible. Gives off irritating or toxic fumes (or gases) in a fire.
Fire PotentialSLIGHT, WHEN EXPOSED TO HEAT OR FLAME. ...CAN REACT WITH OXIDIZING MATERIALS.
Hazards SummaryA skin, eye, and respiratory tract irritant; [ICSC] An irritant; [MSDSonline] See N-Methyl-2-pyrrolidone.
Chemical DangersDecomposes on heating and on burning. This produces toxic fumes including nitrogen oxides.

化学と産業

薬理情報

Mechanism of Action · 3 件

THE MECHANISMS OF SKIN PENETRATION ENHANCERS WERE INVESTIGATED BY MEASURING STEADY-STATE FLUXES IN VITRO FOR MODEL COMPOUNDS, METHANOL, OCTANOL & CAFFEINE. 2-PYRROLIDONE ENHANCED THEIR PERMEATION THROUGH THE POLAR ROUTE OF THE SKIN BY INCREASING THE DIFFUSIVITY & DECREASED PASSAGE THROUGH THE NONPOLAR ROUTE BY DECREASING DIFFUSIVITY & PARTITIONING.

TRYPSINIZED, ABDOMINAL STRATUM CORNEUM ABSORBED 1-4 TIMES ITS WT OF PRIMARY ALCOHOLIC VEHICLE FROM SOLUTIONS OF 0-80% WT 2-PYRROLIDONE IN WATER; ABOUT 2 SEPARATION PARTITION COEFFICIENTS OPERATED. CALCULATIONS OF HM VALUES FOR THE PARTITIONS INDICATED THAT 2-PYRROLIDONE IS PROBABLY NOT A PENETRATION ACCELERANT FOR C1-C8 PRIMARY ALCOHOLS.

FOR THE SIMPLE NONELECTROLYTES TESTED, & UNDER IDEALIZED IN VITRO STEADY STATE CONDITIONS, 2-PYRROLIDONE ACTED AS A MILD ACCELERANT FOR POLAR MATERIAL (METHANOL) DIFFUSION THROUGH HUMAN STRATUM CORNEUM, BUT INHIBITED NONPOLAR, LIPOPHILIC (OCTANOL) TRANSPORT.

Metabolism/Metabolites · 5 件

THE URINARY EXCRETION OF RADIOACTIVE METABOLITES FOLLOWING THE IP ADMIN OF A RANGE OF DOSES OF 2,5-(14)C-2-LABELED N-NITROSOPYRROLIDINE TO RATS WAS EXAMINED. PYRROLIN-2-ONE WAS ONE OF SEVERAL METABOLITES IDENTIFIED.

PYRROLIDONE WAS IDENTIFIED AS A URINARY METABOLITE OF METHADONE.

AN ENZYME SYSTEM RESIDING IN THE SOL FRACTION OF RABBIT LIVER CATALYZES THE CONVERSION OF DELTA 1-PYRROLINE TO GAMMA-AMINOBUTYRIC ACID & ITS LACTAM, 2-PYRROLIDONE.

2-PYRROLIDONE WAS IDENTIFIED AS A METABOLITE OF (14)C-PUTRESCINE IN SLICED RAT LIVER IN VITRO. IT IS ALSO SYNTHESIZED FROM PUTRESCINE BY THE SPLEEN & LUNG, BUT NOT BY KIDNEY, BRAIN, HEART OR MUSCLE.

For more Metabolism/Metabolites (Complete) data for 2-PYRROLIDONE (6 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 1 件

The percutaneous absorption has been investigated in rats of a mixture (3:2, w/w) of N-methyl-2-pyrrolidinone and 2-pyrrolidinone, a combination intended for use as a vehicle in the formulation of an antimycotic drug to enhance skin penetration on dermal application, following co-administration of the two (14)C-radiolabelled compounds by the dermal and oral routes. Radioactivity was excreted predominantly in the urine after either route of administration, and comparison of the respective excretion profiles indicated that about three-quarters of the applied dose was absorbed through the skin. Plasma concentrations of each parent compound, as determined by radio-HPLC, reached peak values at 2 hr after oral dosing, and remained relatively uniform during 1-6 hr after application to the skin, suggesting constant percutaneous absorption during this period. N-Methyl-2-pyrrolidinone appeared to be absorbed through the skin more extensively and at a slightly faster rate than 2-pyrrolidinone; total percutaneous absorption tended to be more extensive in female than in male rats. Together, these two 14C-compounds accounted for most of the plasma radioactivity up to 6-8 hr post-administration. However, by 12 hr (when plasma levels were relatively low), most of the radioactivity was associated with unknown polar metabolites. In view of the extensive percutaneous absorption and little first-pass metabolism of the two pyrrolidinones, the oral route was considered to represent a valid alternative to the dermal route for the assessment of the systemic toxicity of the two compounds.

関連反応

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HRID 40218 の反応式
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HRID 42180 の反応式
HRID 42180反応物としてuspto-grants-2013_09
HRID 51226 の反応式
HRID 51226反応物としてuspto-grants-2004_03
HRID 61523 の反応式
HRID 61523反応物としてuspto-grants-2016_09
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化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
Boiling Point · 3 件

245 °C @ 760 mm Hg; 113-114 @ 9.2 mm Hg; 76 °C @ 0.2 mm Hg

245 °C

245 °C @760 [mm Hg]

DecompositionWHEN HEATED TO DECOMPOSITION IT EMITS TOXIC FUMES OF NITROXIDES.

物理化学的性質

融点
88 · 88-90 °C(lit.)
貯蔵温度
2 · 2-8°C
外見
結晶性粉末およびチャンク
色
赤茶色
水溶解度
アルコール、エーテル、ベンゼン、クロロホルム、二硫化炭素に易溶。水に無限に溶けます。
InChI
InChI=1S/C4H7NO.Br3H/c6-4-2-1-3-5-4;1-3-2/h1-3H2,(H,5,6);3H
InChIKey
GZGCJWMZGQDMLC-UHFFFAOYSA-N
SMILES
O=C1NCCC1.Br(Br)Br

化学的性質

化学的特性red-brown crystalline powder and chunks

NFPA Hazard Classification · 3 件

2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

0 - Materials that in themselves are normally stable, even under fire conditions.

Hazard Classes and Categories · 2 件

Skin Irrit. 2 (17.4%)

Serious eye damage/eye irritation - Category 2

Critical Temperature and PressureCritical Temperature: 802 K; Critical Pressure: 6.17X10+6 Pa

安全と保護具

Fire FightingUse water spray, powder, alcohol-resistant foam, carbon dioxide.
First Aid Measures · 2 件

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Safe StorageVentilation along the floor.
Fire Fighting ProceduresALCOHOL FOAM, CO2, DRY CHEMICAL.
Disposal Methods · 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Spillage DisposalCollect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Eye PreventionWear safety spectacles.
Fire PreventionNO open flames.
Inhalation RiskA harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
Skin PreventionProtective gloves.
Ingestion PreventionDo not eat, drink, or smoke during work.
Effects of Short Term ExposureThe substance is irritating to the skin, eyes and respiratory tract.

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 17(SRC), determined from a structure estimation method(2), indicates that 2-pyrrolidone is expected to have very high mobility in soil(SRC). Volatilization of 2-pyrrolidone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.06X10-9 atm-cu m/mole(3). 2-Pyrrolidone is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.49X10-3 mm Hg(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 17(SRC), determined from a structure estimation method(2), indicates that 2-pyrrolidone is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.06X10-9 atm-cu m/mole(4,SRC). According to a classification scheme(5), an estimated BCF of 3(3,SRC), from a log Kow of -0.85(6), suggests the potential for bioconcentration in aquatic organisms is low.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-pyrrolidone, which has a vapor pressure of 9.49X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-pyrrolidone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 28 hrs(SRC) calculated from its rate constant of 1.35X10-11 cu cm/molecule sec(SRC), determined using a structure estimation method(3).

Exposure RoutesThe substance can be absorbed into the body through the skin.
Signs and Symptoms · 2 件

Redness.

Pain. Redness. Blurred vision.

Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2-pyrrolidone can be estimated to be about 17(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-pyrrolidone is expected to have very high mobility in soil.

Fish/Seafood Concentrations · 1 件

Samples of adult lake trout or walleye collected in 1977 from each of the Great Lakes and Lake St. Clair with each sampling site consisting of 20 large fish composited into one sample; 2-pyrrolidone was detected in trout from Lake Michigan, concentration not specified(1).

Artificial Pollution Sources2-Pyrrolidone's production and use as a precursor to N-vinyl-2-pyrrolidone(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationThrough co-metabolism, 2-pyrrolidone was reported to break down to glutamic acid under aerobic conditions by Bacillus megaterium(1).
Environmental Bioconcentration · 1 件

An estimated BCF of 3 was calculated for 2-pyrrolidone(SRC), using a log Kow of -0.85(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Volatilization from Water/Soil · 1 件

The Henry's Law constant for 2-pyrrolidone is estimated as 1.06X10-9 atm-cu m/mole(SRC) from its vapor pressure, 9.49X10-3 mm Hg(1), and miscibility in water(2). This Henry's Law constant indicates that 2-pyrrolidone is expected to be essentially nonvolatile from water surfaces(3). 2-Pyrrolidone's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces will not occur(SRC). 2-Pyrrolidone is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.49X10-3 mm Hg(1).

Non-Human Toxicity Excerpts · 5 件

PYRROLIDONE ADMINISTERED BY GASTRIC GAVAGE TO RATS SHOWED LD100, LD50, & MAXIMUM TOLERABLE DOSES OF 10, 7.3 & 4 G/KG, RESPECTIVELY. TOPICAL APPLICATION TO THE EYES OF RABBITS CAUSED IRREVERSIBLE CLOUDING OF THE CORNEA.

NO EPILEPTOID ACTIVITY WAS OBTAINED WITH ADMIN OF 4-AMINOBUTYRIC ACID LACTAM (18 MMOL/KG, IP) IN SPRAGUE-DAWLEY RATS. THE EEG WAS DESYNCHRONIZED.

THE EFFECTIVENESS OF A VARIETY OF AMIDE-CONTAINING COMPOUNDS WERE STUDIED TO DETERMINE THE STRUCTURAL FEATURES REQUIRED FOR INDUCTION OF LEUKEMIA CELL DIFFERENTIATION. SUBSTITUED AMIDES WERE EFFECTIVE INDUCERS OF THE DIFFERENTIATION OF MURINE ERYTHROLEUKEMIA (FRIEND) CELLS, AS JUDGED BY THE CELLULAR ACCUMULATION OF HB. ERYTHROID DIFFERENTIATION WAS ASSESSED BY MEASURING THE PERCENTAGE OF BENZIDINE-POSITIVE (IE, HEMOGLOBIN-CONTAINING) CELLS. 2-PYRROLIDONE EXERTED A HIGH INDUCTION (89% BENZIDINE-POSITIVE CELLS) AT A CONCN OF 100 MMOL AFTER 6 DAYS OF CONTINUOUS EXPOSURE.

THE EFFECT OF VARIOUS POLAR ORGANIC COMPOUNDS ON THE OVERALL TRANSCRIPTION OF CHROMATIN FROM FRIEND-VIRUS-INFESTED ERYTHROLEUKEMIA CELLS WITH E COLI RNA POLYMERASE WAS INVESTIGATED. ALL OF THE COMPOUNDS, INCLUDING 2-PYRROLIDONE, WERE FOUND TO STIMULATE TRANSCRIPTION & INDUCE HEMOGLOBIN SYNTHESIS IN FRIEND CELLS. THE OVERALL TRANSCRIPTION INCREASED BY A FACTOR OF 1.3 AT A 230 MMOL CONCN OF 2-PYRROLIDONE.

For more Non-Human Toxicity Excerpts (Complete) data for 2-PYRROLIDONE (11 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 件

The rate constant for the vapor-phase reaction of 2-pyrrolidone with photochemically-produced hydroxyl radicals has been estimated as 1.35X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the reaction of 2-pyrrolidone with the hydroxyl radical in aqueous solution is 2.2X10+9 l/mol sec(2) with a half life of 1 year(SRC) assuming a hydroxyl radical concentration of 1X10-17 mol/l(3). 2-Pyrrolidone is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum.

Probable Routes of Human Exposure · 1 件

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,215 workers (259 of these are female) are potentially exposed to 2-pyrrolidone in the US(1). Occupational exposure to 2-pyrrolidone may occur through inhalation and dermal contact with this compound at workplaces where pyrrolidone is produced or used(SRC). The general population may be exposed to pyrrolidone via ingestion of fish(2) and drinking water(3).

安全データ

wgk
3
hs_code
29337900
risk_code
37/38-41
hazard_code
Xi
safety_code
26-39
Hazard Classifications
Eye Dam. 1Skin Irrit. 2STOT SE 3
ストレージクラス
11 - Combustible Solids
Tissue LocationsBrain
Cellular LocationsCytoplasm

用途と製造

Uses · 5 件

Used as an intermediate in the manufacture of polyvinylpyrrolidone and polypyrrolidone (a polymer, formed in presence of alkaline catalysts); as high-boiling solvent in petroleum processing and acrylonitrile manufacture; in specialty printers inks; as an industrial solvent for polymers, chlordane, DDT, sorbitol, glycerol, iodine, and sugars; as plasticizer and coalescing agent for acrylic-styrene emulsion-type floor polishes; as a chemical intermediate for n-vinyl-2-pyrrolidone and nylon 4 fibers; as a monomer for copolymers with vinyl compounds; as constituent of pharmaceutical preparations; for polyhydroxylic alcohols and ethyl acetate; [HSDB]

Intermediate in mfr of polyvinylpyrrolidone & polypyrrolidone (polymer, formed in presence of alkaline catalysts); used as high-boiling solvent in petroleum processing, acrylonitrile mfr; in specialty printers inks; industrial solvent for polymers, Chlordane, DDT, sorbitol, glycerol, iodine, sugars; as plasticizer & coalescing agent for acrylic-styrene emulsion-type floor polishes

CHEM INT FOR N-VINYL-2-PYRROLIDONE; CHEM INT FOR NYLON 4 FIBERS; SOLVENT; MONOMER FOR COPOLYMERS WITH VINYL COMPOUNDS

USED AS CONSTITUENT OF PHARMACEUTICAL PREPARATIONS

Polyhydroxylic alcohols and ethyl acetate.

U.S. Imports · 2 件

(1972) 6.22X10+7 GRAMS

(1975) 3.23X10+7 GRAMS

U.S. Production · 2 件

2023: 40,000,000 - <55,000,000 lb

(1972) 7.7X10+9 GRAMS

Consumption PatternsOver 95% of the 2-pyrrolidone produced is processed into N-vinyl-2-pyrrolidone.
Consumer UsesOther
Industry UsesOther
Methods of Manufacturing · 3 件

REACTION OF GAMMA-BUTYROLACTONE AND AMMONIA

From acetylene & formaldehyde by high-pressure synth.

Prepd on large scale from butyrolactone by Reppe process.

Household ProductsInformation on 24 consumer products that contain 2-Pyrrolidone in the following categories is provided:
General Manufacturing Information · 2 件

Printing Ink Manufacturing

2-Pyrrolidinone: ACTIVE

応用分野

使用Pyrrolidone hydrotribromide was used as a brominating agent.

一般的な説明Pyrrolidone hydrotribromide has high selectivity for ketones.

上流・下流製品情報

上流原料

カリウムヒドロキシド2-ピロリドンクロロホルム臭素