홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /화합물

피로리돈 하이드로트리브로마이드

2-Pyrrolidone

HCID 12025
새 노트새 반응견적 요청하기
인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
22580-55-8
표준 SMILES
O=C1CCCN1
InChIKey
HNJBEVLQSNELDL-UHFFFAOYSA-N
분자식
C4H7NO
평균 분자량
85.1 g/mol
단동위원소 질량
85.05276385

개요

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.

이름 및 식별자

우선 이름
2-Pyrrolidone
IUPAC
pyrrolidin-2-one
현지명
피로리돈 하이드로트리브로마이드
영어명
Pyrrolidone hydrotribromide
분자식
C4H8Br3NO
분자량
325.83

이름 및 동의어

2-Pyrrolidinonepyrrolidin-2-one616-45-52-PYRROLIDONEPyrrolidoneButyrolactam2-Oxopyrrolidine2-Ketopyrrolidine2-PyrolPyrrolidongamma-Butyrolactamalpha-Pyrrolidinone
이름 더 보기
피로리돈하이드로트리브로마이드PHTSKL178YRROLIDONE 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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
-0.8
극성 표면적
29.1 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
1
회전 가능 결합 수
0
무거운 원자 수
6
형식 전하
0
복잡도
69.9

실험 및 물리화학적 성질

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

log Kow= -0.85

-0.85

-0.85

Density · 3건

1.116 @ 25 °C

Relative density (water = 1): 1.1

1.116 @25 °C

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

CRYSTALS FROM COLD PETROLEUM ETHER

Light yellow liquid

Solubility · 4건

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 · 2건

265 °F (129 °C) (open cup)

129 °C o.c.

Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

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

유해성 정보

Regulatory Information · 4건

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.

화학 및 산업

약리 정보

Mechanism of Action · 3건

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 · 5건

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 · 1건

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.

관련 반응

738건
반응 기록 만들기
HRID 15774 반응식
HRID 15774반응물로uspto-grants-2010_06
HRID 15878 반응식
HRID 15878반응물로uspto-grants-2010_06
HRID 25480 반응식
HRID 25480반응물로uspto-grants-2005_02
HRID 40149 반응식
HRID 40149반응물로uspto-grants-2013_09
HRID 40218 반응식
HRID 40218반응물로uspto-grants-2013_09
HRID 42180 반응식
HRID 42180반응물로uspto-grants-2013_09
HRID 51226 반응식
HRID 51226반응물로uspto-grants-2004_03
HRID 61523 반응식
HRID 61523반응물로uspto-grants-2016_09
1 / 93 페이지

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
더보기
새 노트새 반응견적 요청하기
Boiling Point · 3건

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.

물리화학적 성질

녹는점
88 · 88-90 °C(lit.)
저장 조건
2 · 2-8°C
물리적 상태
결정성 분말 및 덩어리
색상
적갈색
수용성
알코올, 에테르, 벤젠, 클로로포름, 이황화탄소에 매우 강한 졸입니다. 물에 무한히 용해됩니다.
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

화학적 성질

red-brown crystalline powder and chunks

NFPA Hazard Classification · 3건

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 · 2건

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

안전 및 보호

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

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 · 1건

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.

독성 정보

Environmental Fate · 3건

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 · 2건

Redness.

Pain. Redness. Blurred vision.

Soil Adsorption/Mobility · 1건

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 · 1건

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 · 1건

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 · 1건

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 · 5건

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 · 1건

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 · 1건

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).

안전 데이터

wgk
3
HS 번호
29337900
risk_code
37/38-41
hazard_code
Xi
safety_code
26-39
Hazard Classifications
Eye Dam. 1Skin Irrit. 2STOT SE 3
스토리지 클래스
11 - Combustible Solids
Tissue LocationsBrain
Cellular LocationsCytoplasm

용도 및 제조

Uses · 5건

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 · 2건

(1972) 6.22X10+7 GRAMS

(1975) 3.23X10+7 GRAMS

U.S. Production · 2건

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 · 3건

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 · 2건

Printing Ink Manufacturing

2-Pyrrolidinone: ACTIVE

응용 분야

용도Pyrrolidone hydrotribromide was used as a brominating agent.

일반 설명Pyrrolidone hydrotribromide has high selectivity for ketones.

상·하류 제품 정보

상류 원료

수산화칼륨2-피롤리디논클로로포름브롬