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Pyrrol Produkt Beschreibung

Pyrrole Struktur
109-97-7
CAS-Nr.
109-97-7
Bezeichnung:
Pyrrol
Englisch Name:
Pyrrole
Synonyma:
AZOLE;Pyrrol;PYRROLE;Pyrrhol;Parzate;IMIDOLE;Pyrroline;FEMA 3386;1H-PYRROLE;Pyrrole>
CBNumber:
CB3852794
Summenformel:
C4H5N
Molgewicht:
67.09
MOL-Datei:
109-97-7.mol

Pyrrol Eigenschaften

Schmelzpunkt:
-23 °C (lit.)
Siedepunkt:
131 °C (lit.)
Dichte
0.967 g/mL at 25 °C (lit.)
Dampfdichte
2.31 (vs air)
Dampfdruck
8.7 hPa (20 °C)
FEMA 
3386 | PYRROLE
Brechungsindex
n20/D 1.508(lit.)
Flammpunkt:
92 °F
storage temp. 
Store at +2°C to +8°C.
Löslichkeit
60g/l
pka
15(at 25℃)
Aggregatzustand
Liquid
Farbe
Clear almost colorless to brownish
PH
>6 (10g/l, H2O, 20℃)
Explosionsgrenze
3.10-14.8%(V)
Wasserlöslichkeit
60 g/L (20 ºC)
Sensitive 
Air & Light Sensitive
JECFA Number
1314
Merck 
14,8014
BRN 
1159
Stabilität:
Stable. Incompatible with strong acids, strong oxidizing agents. Combustible.
InChIKey
KAESVJOAVNADME-UHFFFAOYSA-N
CAS Datenbank
109-97-7(CAS DataBase Reference)
NIST chemische Informationen
Pyrrole(109-97-7)
EPA chemische Informationen
1H-Pyrrole (109-97-7)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher T
R-Sätze: 10-20-25-41
S-Sätze: 26-37/39-45-39-24-16
RIDADR  UN 1992 3/PG 3
WGK Germany  2
RTECS-Nr. UX9275000
8-10-23
Selbstentzündungstemperatur 550 °C
TSCA  Yes
HazardClass  3
PackingGroup  III
HS Code  29339900
Giftige Stoffe Daten 109-97-7(Hazardous Substances Data)
Toxizität LD50 orally in Rabbit: 137 mg/kg
Bildanzeige (GHS)
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H226 Flüssigkeit und Dampf entzündbar. Entzündbare Flüssigkeiten Kategorie 3 Warnung
H301 Giftig bei Verschlucken. Akute Toxizität oral Kategorie 3 Achtung P264, P270, P301+P310, P321, P330,P405, P501
H311 Giftig bei Hautkontakt. Akute Toxizität dermal Kategorie 3 Achtung P280, P302+P352, P312, P322, P361,P363, P405, P501
H318 Verursacht schwere Augenschäden. Schwere Augenschädigung Kategorie 1 Achtung P280, P305+P351+P338, P310
H331 Giftig bei Einatmen. Akute Toxizität inhalativ Kategorie 3 Achtung P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H332 Gesundheitsschädlich bei Einatmen. Akute Toxizität inhalativ Kategorie 4 Warnung P261, P271, P304+P340, P312
Sicherheit
P210 Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P233 Behälter dicht verschlossen halten.
P240 Behälter und zu befüllende Anlage erden.
P261 Einatmen von Staub vermeiden.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P271 Nur im Freien oder in gut belüfteten Räumen verwenden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P301+P310 BEI VERSCHLUCKEN: Sofort GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

Pyrrol Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R10:Entzündlich.
R20:Gesundheitsschädlich beim Einatmen.
R25:Giftig beim Verschlucken.
R41:Gefahr ernster Augenschäden.

S-Sätze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S39:Schutzbrille/Gesichtsschutz tragen.
S24:Berührung mit der Haut vermeiden.
S16:Von Zündquellen fernhalten - Nicht rauchen.

Aussehen Eigenschaften

C4H5N; Klare, fast farblose Flüssigkeit die an Licht über gelb zu bräunlich nachdunkelt. Schwach aromatischer Geruch. Luft-, feuchtigkeits und lichtempfindlich.

Gefahren für Mensch und Umwelt

Entzündlich. Nicht mit Salzsäure und Oxidationsmitteln in Berührung bringen.

LD50 (oral, Ratte) 158 mg/kg

Schutzmaßnahmen und Verhaltensregeln

Dicht verschlossen, kühl (0 bis + 6鳦) unter Lichtschutz, an gut belüftetem Ort, nicht in der Nähe von brennbaren Stoffen.
Schutzhandschuhe als kurzzeitiger Spritzschutz

Verhalten im Gefahrfall

Mit flüssigkeitsbindendem Material z.B. Rench Rapid aufnehmen. Der Entsorgung zuführen. Nachreinigen.
Kohlendioxid, Pulver, Schaum
Brennbar. Bildung explosionsfähiger Gemische mit Luft möglich. Im Brandfall können entstehen: NOx.

Erste Hilfe

Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 10 Minuten ausspülen.
Nach Einatmen: Frischluft.
Nach Verschlucken: Viel Wasser trinken lassen, Erbrechen auslösen. Bei Unwohlsein Arzt konsultieren.
Nach Kleidungskontakt: Kontaminierte Kleidung sofort entfernen.
Ersthelfer: siehe gesonderten Anschlag

Sachgerechte Entsorgung

Vorsichtige Neutralisation mit verdünnter Salz- oder Schwefelsäure. Halogenhaltige organische Lösemittelabfälle.

Chemische Eigenschaften

colourless to brown liquid with chloroform odour

Chemische Eigenschaften

Six π-electrons are distributed over the five ring atoms of pyrrole. Delocalization of these electrons stabilizes the ring and the lone pair of electrons on the nitrogen atom, which is responsible for the usual basicity of nitrogen compounds, is involved in the electron cloud, and is not available for sharing. Hence, pyrrole is an extremely weak base and the pyrrolic nitrogen is not readily susceptible to electrophilic enzymic attack (Damani, 1985). There is a high electron density, however, at all positions of the ring, which causes pyrrole to be reactive toward electrophilic substitution. In general, electrophilic substitution reactions on the neutral molecule occur preferentially at the C-2 or C-5 positions (Jones and Bean, 1977; Damani and Crooks, 1982).

Chemische Eigenschaften

Pyrrole has a sweet, warm-ethereal odor reminiscent of chloroform

Occurrence

The pyrrole ring is the basic unit of the porphyrin system which occurs, for example, in chlorophyll and in hemoglobin. Other pyrrole-based natural products include pigments such as bilirubin and biliverdin, which are degradative products from porphyrins (Sundberg, 1984).
Pyrrole has been found in surface waters and in filtrates from cultures of the blue-green algae, Anabaenaflos aquae. The presence of pyrrole and other organic nitrogen compounds in natural waters is of environmental concern because they may exert significant chlorine demand. Pyrrole is also a precursor to trihalomethane formation (Ram and Morris, 1980).
At ambient temperature, pyrrole can be volatilized from shale oil wastewaters. Concentrations of approximately 3 g/m3 have been measured indoors in air at an oil shale wastewater facility (Hawthorne and Sievers, 1984). Pyrrole has been identified in tobacco smoke, although not in tobacco itself (Johnstone and Plim-mer, 1959); in cigarette smoke (Schumacher et al 1977); in cigar butt aroma (Peck et al 1969); and in Cannabis smoke condensate (Jones and Foote, 1975).
Pyrrole was found to be naturally occurring in foods; in fact, it is on the Food and Drug Administration GRAS (Generally Recognized As Safe) list, with an average usage level of 3 p.p.m. in flavoring formulations (Maga, 1981). Pyrrole is a volatile constituent of roasted coffee (Gianturco et al 1966), roasted peanuts (Walradt et al 1971), and fried chicken (Tang et al 1983). It has also been identified in beef aroma (MacLeod and Coppock, 1976) and is a constituent of cocoa aroma (Marion et al 1967). It should be noted that all the foods listed have undergone some degree of thermal treatment; pyrrole was not present in the fresh, raw foods. In model system studies, pyrrole was among the resulting compounds when hydroxyproline and glucose were heated under nitrogen at temperatures ranging from 120° to 200°C. Large amounts of pyrrole were found, as well, when casein and collagen were pyrolyzed and when proline underwent high temperature pyrolysis (Maga, 1981).

Verwenden

Manufacture of pharmaceuticals.

Verwenden

Commercial applications of this compoundare very limited. It is used in organic synthesis.Pyrrole is formed by heating albumin orby pyrolysis of gelatin.

Definition

pyrrole: An organic nitrogencontainingcompound that formspart of the structure of porphyrins.

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.

Vorbereitung Methode

Pyrrole may be made (1) by reaction of succinimide with zinc and acetic acid, or with hydrogen in the presence of finely divided platinum heated, (2) by reaction of ammonium saccharate or mucate COONH4·(CHOH)4·COONH4 with glycerol at 200 °C by loss of carbon dioxide, ammonia, and water. When pyrrole is treated with potassium (but not with sodium) or boiled with solid potassium hydroxide, potassium pyrrole C4H4NK is formed, which is the starting point for N-derivatives of pyrrole, since reaction of the potassium with halogen of organic compound and with carbon dioxide, readily occurs.

Vorbereitung Methode

Pyrrole originally was prepared industrially by fractional distillation of coal tar, bone oil or other protein material, and purified through formation of its potassium derivative (Runge, 1834; Michelman, 1925). Later it was produced by heating ammonium mucate with glycerol or mineral oil (Blicke and Powers, 1927; McElvain and Bollinger, 1941). It is now manufactured by addition of ammonia to either acetylene or butadiene. Good yields of pyrrole also may be obtained from the reaction of ammonia with the corresponding heterocyclic compound (furan) in a vapor-phase process at 480° to 500°C, using alumina as a catalyst (Thompson, 1972) or by catalytic reaction of furan with ammonia over a molybdenum or vanadium oxide catalyst at 350-400°C (Bishop and Denton, 1950).

Definition

ChEBI: A tautomer of pyrrole that has the double bonds at positions 2 and 4.

Aroma threshold values

Detection: 20 to 49.6 ppm

Hazard

Moderate fire risk. Toxic by ingestion and inhalation.

Health Hazard

The toxicity data on pyrrole are scant. Itis moderately toxic on test animals. Theroutes of exposure are inhalation of vapors,ingestion, and skin absorption. Vapors arean irritant to the eyes and respiratory tract.The lethal doses in rabbits by oral anddermal routes are within the range 150 and250 mg/kg, respectively.

Health Hazard

Pyrrole is harmful if swallowed, inhaled, or absorbed through the skin. Its vapor or mist is irritating to the eyes, mucous membranes and upper respiratory tract (Lenga, 1985; Sax, 1984). Although no cases of occupational disease due to pyrrole have been reported, it has a depressant action on the central nervous system and, in severe intoxication, it is injurious to the liver. Tests indicate that it has moderate cumulative toxicity (Parmegianni, 1983).

Brandgefahr

Combustible liquid; flash point (closed cup) 39°C (102°F); vapor forms explosive mixtures with air; LEL and UEL values are not available. Heating with strong oxidizers can be violent.

Industrielle Verwendung

Pyrrole is a five-member nitrogen heterocyclic ring that contains two carbon-carbon double bond configurations which gives the solvent a pronounced aromatic character. Pyrrole is an intermediate in the synthesis of a variety of commercial chemical derivatives. Pyrrole has only limited solubility in water but are miscible with many organic solvents.Pyrrole when freshly distilled is a colorless liquid, but the solvent can rapidly acquire a brown coloration due to air oxidation. Prolonged standing in the air will promote slow polymerization of the pyrrole to give a dark brown polymer. Pyrrole has a viscosity of 1.31 centipoise and a medium surface tension value of 37.1 dynes/cm.
pyrrole is used as a chemical intermediate in the preparation of electrically conducting polypyrrole by means of an electrochemical polymerization process. Pyrrole has few other industrial uses.

Industrielle Verwendung

Pyrrole is used to a limited extent as a solvent for polymeric esters, but its primary value lies in its function as a chemical intermediate. It is used in the synthesis of non-heterocyclic compounds (Kozikowski, 1984) and its derivatives have been used in the manufacture of dyes, herbicides, perfumes, and as cross-linking agents for curing resins (Thompson, 1972). Derivatives of pyrrole are utilized in pharmaceutical applications, particularly as anti-inflammation drugs and drugs with central nervous system activity, including antihypertensive effects (Sundberg, 1984); and as antimicrobial agents (Freeman, 1975), such as fungicides (Zirngibl, 1983) and bactericides (Bailey and Johnson, 1973; Bailey et al 1973; Sundberg, 1984). Polymers of pyrrole have been used in the preparation of photoconductive materials. The main utility of poly(pyrrole) has been for the modification of electrode surfaces, although numerous other applications can be envisioned (Heilmann and Rasmussen, 1984).

Sicherheitsprofil

Poison by ingestion, subcutaneous, and intraperitoneal routes. Flammable liquid when exposed to heat or flame; can react with oxilzing materials. To fight fire, use foam, CO2, dry chemical. Violent reaction with 2-nitrobenzaldehyde. When heated to decomposition it emits highly toxic fumes of NOx.

Stoffwechsel

Reports concerning the metabolites formed following administration of pyrrole have been somewhat confusing. Saccardi (1919a, 1920) observed that administration of pyrrole orally and by injection resulted in the formation of melanin in the urine of rabbits, but not of dogs. Unchanged pyrrole was also found in the urine of rabbits after injection of pyrrole (Saccardi, 1919b). Shimizu (1921) isolated methylpyridine from the urine of rabbits and dogs given pyrrole and suggested that pyrrole could be converted to pyridine derivatives in vivo. The transformations in the body and the excretion products in the urine are, however, in question (Fairhall, 1969). Novello (1927) injected rabbits subcutaneously with 0.5 g doses of pyrrole hydrochloride and attempted to detect acetyl or methyl derivatives, but was unsucessful. Approximately 40-50% of the nitrogen of the injected pyrrole was excreted as urea. By the process of elimination, Novello (1927) concluded that the nitrogen not accounted for as urea nitrogen was excreted as unchanged pyrrole. It did not appear that the pyrrole was oxidized to a secondary or tertiary alcohol because there was no rise in ethereal sulfate or conjugated glucuronic acid excretion. Kusui (1935) injected frogs with pyrrole and noted that although the urine smelled of pyrrole, no free base could be isolated. Damani and Crooks (1982) have suggested that pyrrole may be a likely substrate for hydroxylation at C-2 and C-5, leading to ring opened products. They have not, however, studied the biotransformation of pyrrole, but based their hypothesis on studies of the metabolism of indole.
Pyrrole may affect the biotransformation of other compounds. Bernheim et al (1938) observed that pyrrole acted as a catalyst for the oxidation of amines and certain non-natural amino acids and catalyzed the formation of methemoglobin from hemoglobin. On the other hand, pretreatment of rats with 100 mg/kg pyrrole inhibited markedly the metabolism of dimethylnitrosamine in terms of both C02 excretion and decline in blood dimethylnitrosamine concentration (Phillips et al 1982).

läuterung methode

Dry pyrrole with NaOH, CaH2 or CaSO4. Fractionally distil it under reduced pressure from CaH2. Store it under nitrogen as it turns brown in air. Redistil it immediately before use. The picrate forms orange-red crystals with m 69o(dec). [Beilstein 20 H 4, 20 I 3, 20 II 3, 20 III/IV 61, 20/5 V 3.]

Pyrrol Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Pyrrol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 295)Lieferanten
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate
Jiangsu Qingquan Chemical Co., Ltd.
+86-571-86589381/86589382/86589383
lyy@qqpharm.com sales1@qqpharm.com CHINA 154 55
Capot Chemical Co.,Ltd.
+86(0)13336195806 +86-571-85586718
+86-571-85864795 sales@capotchem.com China 20012 60
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8909 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29955 58
NINGBO INNO PHARMCHEM CO., LTD.
13867897135
sales@nbinno.com CHINA 925 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293
+86 0531-67809011 sales@sdzschem.com CHINA 2941 58
Chongqing Chemdad Co.,Ltd
+86-19923101450
sales@chemdad.com CHINA 4000 58
Xiamen AmoyChem Co., Ltd
+86 592-605 1114
sales@amoychem.com CHINA 6369 58
Hubei xin bonus chemical co. LTD
86-13657291602
027-59338440 linda@hubeijusheng.com CHINA 23035 58
Shandong chuangyingchemical Co., Ltd.
18853181302
sale@chuangyingchem.com CHINA 5917 58

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