Pyrrol

1H-PYRROLE · AZOLE · Pyrroline · Pyrrol · IMIDOLE · FEMA 3386 · Parzate · 1H-Pyrrole 98%

Identifikatoren & physikalische Daten

CAS No.	109-97-7
Summenformel	C4H5N
Durchschnittliche Molmasse	67,09 g/mol
Monoisotopische Masse	67,04219916 g/mol
SMILES	c1cc[nH]c1
InChIKey	KAESVJOAVNADME-UHFFFAOYSA-N
PubChem CID	8027
ChEMBL	CHEMBL16225
ChEBI	CHEBI:19203
EC No.	203-724-7
DTXSID	DTXSID5021910
Lokaler Name	Pyrrol

Chemische & physikalische Eigenschaften

XLogP	0,7
Polarare Oberfläche (TPSA)	15,8
H-Brücken-Donoren	1
H-Brücken-Akzeptoren	0
Frei drehbare Bindungen	0
Schwere Atome	5
Formalladung	0
Komplexität	22,8
Stoffklassen	Nitrogen Compounds -> Pyrroles
SpringerMaterials Properties	15N nuclear magnetic resonance spectrum
LogP (Verteilungskoeffizient)	log Kow = 0.75
Geruch	Agreeable empyreumatic odor resembling that of chloroform
Geschmack	Burning, pungent taste
Lebensmittelzusatzstoffe	FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Dichte	0.9698 @ 20 °C0.955-0.9750.9698 @ 20°C0.967 g/mL at 25 °C (lit.)
Aromastoffe	EU Flavoring substances
Viscosity	4.1123X10-3 Pa.s @ 249.74K
Color/Form	Colorless liquid when freshYellowish or brown oil
Löslichkeit	Soluble in alcohol, ether and dilute acids. Also soluble in most organic chemicals.Water solubility: 4.5X10+4 mg/l @ 25 °C45 mg/mL at 25 °CSoluble in most fixed oilsSlightly soluble in waterSoluble (in ethanol)60g/l60 g/L (20 ºC)
Flammpunkt	102 °F (39 °C) (CLOSED CUP)92 °F
Schmelzpunkt	-23 °C (lit.)
Siedepunkt	131 °C (lit.)
Dampfdichte	2.31 (vs air)
Dampfdruck	8.7 hPa (20 °C)
FEMA	3386 \| PYRROLE
Brechungsindex	n20/D 1.508(lit.)
Lagerbedingungen	Store at +2°C to +8°C.
pKa (Säurekonstante)	15(at 25℃)
Aggregatzustand	Liquid
Farbe	Clear almost colorless to brownish
pH	>6 (10g/l, H2O, 20℃)
Geruch	at 0.10 % in propylene glycol. sweet warm nutty ethereal
Geruchsart	nutty
Biologische Quelle	synthetic
Explosionsgrenze	3.10-14.8%(V)
Spezifische Wärmekapazität	Cp(liquid): 1.9 J/(g·K), at 25℃
JECFA Number	1314
Merck	14,8014
BRN	1159
Henry-Konstante	5.5×10-1 mol/(m3Pa) at 25℃, Hawthorne et al. (1985)
Dielektrizitätskonstante	7.5(17℃)
Stabilität	Stable. Incompatible with strong acids, strong oxidizing agents. Combustible.
Hauptanwendungen	flavors and fragrances
InChI	1S/C4H5N/c1-2-4-5-3-1/h1-5H
InChIKey	KAESVJOAVNADME-UHFFFAOYSA-N
SMILES	c1cc[nH]c1
LogP (Verteilungskoeffizient)	0.85
Oberflächenspannung	36.6mN/m at 20°C
CAS Datenbank	109-97-7(CAS DataBase Reference)
NIST chemische Informationen	Pyrrole(109-97-7)
EPA chemische Informationen	1H-Pyrrole (109-97-7)

Sicherheit & Vorschriften

GHS-Einstufung	WarningH226 (10.7%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P317, P303+P361+P353, P330, P370+P378, P403+P235, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1442 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H226: Flammable liquid and vapor [Warning Flammable liquids]
Regulatorische Informationen	Chemical: 1H-PyrroleCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 22-05-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/310751H-Pyrrole: Does not have an individual approval but may be used under an appropriate group standard
Brandpotenzial	Flammable liquid when exposed to heat or flame ...
Gefahrenübersicht	A CNS depressantMay cause liver injuryEffects of high doses administered by IP injection in dogs include convulsions and liver injury[HSDB] Safe when used as a flavoring agent in food[JECFA] Causes convulsions and muscle contractions in oral lethal-dose studies of rabbits[RTECS]
NFPA Hazard Classification	2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.0 - Materials that in themselves are normally stable, even under fire conditions.
Hazard Classes and Categories	Flam. Liq. 3 (10.7%)Flammable liquids - Category 3
Critical Temperature and Pressure	Critical temperature: 366.75 °CCritical pressure: 6.21X10+6 Pa
Hazardous Reactivities and Incompatibilities	... CAN REACT WITH OXIDIZING MATERIALS.Violent reaction with 2-nitrobenzaldehyde.
Brandbekämpfungsverfahren	FOAM, CARBON DIOXIDE, DRY CHEMICAL.
Entsorgungsverfahren	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.
Protective Action Criteria (PAC)	0.32 [mg/m3]3.5 [mg/m3]21 [mg/m3]
Personal Protective Equipment (PPE)	IN VIEW OF THE COMPOUND'S RELATIVELY LOW TOXICITY, ORDINARY HANDLING PRECAUTIONS INCLUDING USE OF GLOVES & GOOD VENTILATION ARE ADEQUATE TO PREVENT INJURY.
Umweltverhalten	TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 61(SRC), determined from a log Kow of 0.75(2) and a regression-derived equation(3), indicates that pyrrole is expected to have high mobility in soil(SRC). Volatilization of pyrrole from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.8X10-5 atm-cu m/mole(4). The potential for volatilization of pyrrole from dry soil surfaces may exist(SRC) based upon a vapor pressure of 8.35 mm Hg(5). Pyrrole does not readily undergo biodegradation in water unless there exists bacteria that have had previous exposure to pyrrole. Given this need for acclimation, the decomposition of pyrrole may be very slow(6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 61(SRC), determined from a log Kow of 0.75(2), indicates that pyrrole is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water sources is expected(3) based upon a Henry's Law constant of 1.80X10-5 atm-cu m/mole(4). Volatilization half-lives for a model river and model lake are 42 hrs and 368 hrs, respectively(SRC), using an estimation method(3). According to a classification scheme(5), an estimated BCF of 2(3,SRC) from a log Kow of 0.75(2) suggests the potential for bioconcentration in aquatic organisms is low. Experiments have shown that pyrrole is actually degraded by gasoline-adapted ground water cultures when present as a single substrate. Adaption time was 480 hrs and degradation time was 600 hrs(6). Pyrrole was not degraded in a mixture of compounds in water after 1100-1300 hrs at 10 °C and at a concentration of 0.2-1 mg/l(6).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pyrrole, which has a vapor pressure of 8.35 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase pyrrole 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 4 days(SRC) from its rate constant of 1X10-10 cu cm/molecule sec(3). In a comparison of room temperature rate constants and loss rates of selected organics in the presence of 7.2X10+11 molecule/cu cm of ozone, 5X10+5 molecule/cu cm of hydroxyl radicals, and 2.4X10+8 molecules/cu cm of NO3 radicals, pyrrole displayed the following rate constants: 1.6X10-17 cu cm/molecule sec with a loss rate of 1 day, 1.2X10-11 cu cm/molecule sec with a loss rate of 5.2 days, and 4.9X10-11 cu cm/molecule sec with a loss rate of 1000 days, respectively(4).
Lebensmitteluntersuchungswerte	Pyrrole has been detected in "popped" popcorn at a level of 26 ug/kg in a dry capture method and 44 ug/kg in a wet capture method(1). Fresh chicken breast with bone was cut into 1.5 inch cubes, coated with flour and fried in Fri-al shortening. During a 48 hour period in which the chicken was fried, pyrrole was detected (detection level not specified)(2).
Unerwünschte Wirkungen	Neurotoxin - Other CNS neurotoxin
Effluent Concentrations	Results of a study of several sites show that prior to coal gasification by ground water, pyrrole was not detected (limits of detection were 0.1 ppb). However, once coal gasification began, pyrrole was detected at 208 ppm in Hanna, Wyoming and 111 ppm Gillete, Wyoming. Pyrrole was not detected from low-Btu gasification of Rosebud coal but was detected at 23 ppm from an in situ oil shale process (limits of detection were 0.1 ppb)(1). Two retort wastewaters selected for study were produced from January to May, 1979 in the modified in situ retort 6 at the Occidental Oil Shale, Inc. facility at Logan Wash, CO. In the condensate retort water, 4.9 mg/l of pyrrole was detected while no pyrrole was detected at the process retort water (detection limits not specified)(2). Pyrrole was detected from shale oil wastewaters used to cool hot spent shale, both in gas condensate water and process retort water units not specified(3).
Medical Surveillance	...PERSONS WITH ABNORMAL RESPIRATORY, CIRCULATORY OR LIVER CONDITIONS SHOULD NOT BE EXPOSED TO THIS SUBSTANCE.
Soil Adsorption/Mobility	The Koc of pyrrole is estimated as approximately 61(SRC), using a log Kow of 0.75(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that pyrrole is expected to have high mobility in soil.
Atmospheric Concentrations	SOURCE DOMINATED: Pyrrole was detected at <1 ng/ml of air above 1 ml of water in 10 ml samples from two process retort wastewaters collected at Laramie Energy Technology Center during May 1982 and at the Logan Wash site of Occidental Oil Shale Inc. during December 1987it was also detected in the gas-condensate retort wastewaters at 3.1 and 5.0 ng/ml of air above 1 ml of water at both sites(1). Pyrrole has been found in stock emission during incineration of municipal waste units not specified(2). URBAN/SUBURBAN: Pyrrole was not detected in ambient air at either Logan Wash, CO or at Boulder, CO(1).
Human Toxicity Excerpts	IT HAS A DEPRESSANT ACTION ON THE CENTRAL NERVOUS SYSTEM AND, IN SEVERE INTOXICATION, IS INJURIOUS TO THE LIVER.NO CASES OF OCCUPATIONAL DISEASE DUE TO PYRROLE HAVE BEEN REPORTEDHOWEVER TESTS INDICATE THAT IT HAS A MODERATE CUMULATIVE TOXICITY.
Artificial Pollution Sources	Pyrrole's production and presence in creosote(1), chemical intermediate in drug manufacturing(2) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation	AEROBIC: Pyrrole was not degraded in a mixture of compounds in water after 1100-1300 hrs at 10 °C and at a concentration of 0.2-1 mg/l. Experiments have shown that pyrrole is actually degraded by gasoline-adapted ground water cultures when present as a single substrate. Adaption time was 480 hrs and degradation time was 600 hrs. Pyrrole inhibits benzene biodegradation strongly even at pyrrole concentrations of 100-200 ug/l(1). Degradation of pyrrole seems to be enhanced with the concomitant degradation of other compounds in an aqueous environment. No degradation of pyrrole was observed under denitrifying conditions during 846 days of incubation(2). In an aerobic enrichment culture that originated from groundwater at a creosote-contaminated aquifer in Fredensbury Denmark, pyrrole was completely removed after 49 days. It is suggested that microorganisms have to adapt to pyrrole before they can begin to degrade it and that the lag phase can be very long(3).ANAEROBIC: Anaerobic research of pyrrole using primary digestive sludge, having an average inflow of 100 cu m/day and a mean retention time of 20 days, displayed negative gas production during the first 11 weeks of incubation. This corresponds to no biodegradation of pyrrole under anaerobic conditions(1).
Sediment/Soil Concentrations	Pyrrole is a constituent of creosote which is a compound used as a wood preservative, especially in electric poles. Due to this, pyrrole may be found in soil in locations where creosote has been used(1).
Environmental Bioconcentration	An estimated BCF of 2 was calculated for pyrrole(SRC), using a log Kow of 0.75(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low.
F	8-10-23
Wassergefährdungsklasse (WGK)	2
TSCA-Inventar-Status	TSCA listed
UN-Transportnummer	UN 1992 3/PG 3
Zollcode	29339900
RTECS-Nr.	UX9275000
R-Sätze (R)	10-20-25-41
Toxizität	LD50 orally in Rabbit: 137 mg/kg
Gefahrensymbole	T
Sicherheitshinweise (S)	26-37/39-45-39-24-16
Gefahrenklasse	3Acute Tox. 3 OralAcute Tox. 4 InhalationEye Dam. 1Flam. Liq. 3
Verpackungsgruppe	III
Lagerklasse	3 - Flammable liquids
Gefahrstoffdaten	109-97-7(Hazardous Substances Data)
Selbstentzündungstemperatur	550 °C

Anwendungen & Verwendung

Beschreibung

Pyrrol ist eine farblose, stark lichtbrechende Flüssigkeit, die bei 127-130 ℃ siedet und in Wasser schlecht löslich ist, dafür aber gut in Ethanol und Ether. Der Nachweis von Pyrrol erfolgt durch die Fichtspan-Reaktion, oder durch die Zeitungspapier-Reaktion. Bei der Fichtspan-Reaktion färben Pyrroldämpfe einen mit Salzsäure befeuchteten Fichtenspan rot. Dieser Reaktion verdankt das Pyrrol wahrscheinlich auch seinen Namen (pyrros = feuerrot). Bei der Zeitungspapier-Reaktion wird ein Tropfen Pyrrol auf einer Zeitung eintrocknen gelassen, die dann mit Salzsäuredämpfen in Kontakt gebracht wird. Auch hier zeigt eine dunkelrote Färbung die Anwesenheit von Pyrrol an. Beide Nachweisreaktionen beruhen wahrscheinlich darauf, dass Pyrrol durch Kondensation mit aromatischen Aldehydgruppen des Lignins rote Farbstoffe bildet. Eine andere Nachweisreaktion ist die Ehrlich-Reaktion mit p-Dimethylaminobenzaldehyd.

Herstellung & Synthese

synthetische

By fractional distillation of bone oil (bone oil is obtained by destructive distillation of animal bone) and subsequent purification via the corresponding potassium salt; by thermal decomposition of ammonium mucate in glycerol or mineral oil.