Benzimidazol

Bezeichnung:Benzimidazol

CAS-Nr51-17-2

Englisch Name:Benzimidazole

CBNumberCB2177003

SummenformelC7H6N2

Molgewicht118.14

MOL-Datei51-17-2.mol

Synonyma

Benzimidazol

Benzimidazol physikalisch-chemischer Eigenschaften

Schmelzpunkt	169-171 °C (lit.)
Siedepunkt	360 °C
Dichte	1.1151 (rough estimate)
Brechungsindex	1.5500 (estimate)
Flammpunkt	360°C
storage temp.	Store below +30°C.
Löslichkeit	xylene: soluble1g in 2g (boiling)(lit.)
Aggregatzustand	Crystalline Powder or Crystals
pka	5.532(at 25℃)
Farbe	Beige to brown
Wasserlöslichkeit	sparingly soluble
maximale Wellenlänge (λmax)	271nm(MeOH)(lit.)
Merck	14,1081
BRN	109682
Henry's Law Constant	2.7×10¹ mol/(m³Pa) at 25℃, HSDB (2015)
Stabilität	Stable. Combustible. Incompatible with strong oxidising agents.
InChI	1S/C7H6N2/c1-2-4-7-6(3-1)8-5-9-7/h1-5H,(H,8,9)
InChIKey	HYZJCKYKOHLVJF-UHFFFAOYSA-N
SMILES	c1ccc2[nH]cnc2c1
LogP	1.320
CAS Datenbank	51-17-2(CAS DataBase Reference)
NIST chemische Informationen	1H-Benzimidazole(51-17-2)
EPA chemische Informationen	Benzimidazole (51-17-2)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	37/39-26-24/25
WGK Germany	3
RTECS-Nr.	DD5425000
Hazard Note	Irritant
TSCA	TSCA listed
HS Code	29339990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral
Giftige Stoffe Daten	51-17-2(Hazardous Substances Data)
Toxizität	LD50 oral in mouse: 2910mg/kg

Gefahreninformationscode (GHS)

Benzimidazole Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Chemische Eigenschaften
Benzimidazole is a sheet-like white crystal, with a temperature of 170 ℃, soluble in water and ethanol. Usually used as template compound in the preparation of molecularly imprinted polymer via electropolymerization and electrodeposition of pyrrole on a pencil graphite electrode,and also used in the preparation of benzimidazolium surfactant, 1-hexadecyl-1H-benzimidazole.
Verwenden
Benzimidazole is a building block for making anthelmintic drugs like albendazole, mebendazole and triclabendazole and anti-ulcer drugs like pantoprazole, rabeprazole, lansoprazole and omeprazole. It is used in the preparation of pyrene derived benzimidazole linked polymers (BILPs), which are used for selective carbon dioxide separation applications due to their properties like porous materials, regenerability and sorbent selection parameters.
synthetische
Benzimidazole is synthesized by cyclizing o-phenylenediamine with formic acid. A mixture of o-phenylenediamine and formic acid is heated in a water bath for 2 hours, then cooled. The pH is adjusted to 10 using 10% sodium hydroxide solution, followed by filtration of the precipitated solid. The solid is washed with cold water to obtain the crude product (yield: 90%). The crude product is then refluxed in water, decolorized with activated carbon, and hot-filtered. Upon cooling the filtrate to room temperature, the purified product is collected by filtration, washed with cold water, and dried at 100°C to obtain the final product.
Definition
ChEBI: 1H-benzimidazole is the 1H-tautomer of benzimidazole. It is a benzimidazole and a polycyclic heteroarene. It is a conjugate acid of a benzimidazolide. It is a tautomer of a 4H-benzimidazole, a 2H-benzimidazole and a 3aH-benzimidazole.
Allgemeine Beschreibung
White tabular crystals.
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
An amine. Neutralizes acids to form salts plus water. These acid-base reactions are exothermic. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides. May be shock sensitive.
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition Benzimidazole emits highly toxic fumes.
Brandgefahr
Flash point data for Benzimidazole are not available. Benzimidazole is probably combustible.
Pharmakologie
The mode of action of benzimidazoles has been described in several comprehensive reviews (1,32,33). The primary mode of action of benzimidazoles has been identified as the specific binding to the β-subunit of fungal tubulin and, consequently, an interference with microtubule assembly. Microtubules are major components of the fungal cytoskeleton and are involved in meiosis and mitosis, both of which are blocked in the presence of benzimidazoles.
Sicherheitsprofil
Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits highly toxic fumes of NOx.
läuterung methode
It crystallises from water or aqueous EtOH (charcoal) and is dried at 100o for 12hours. [Beilstein 23 H 131, 23/6 V 196.]
Einzelnachweise
[1] YEUAN TING LEE Chern E O Yi Jer Tan. Benzimidazole and its derivatives as cancer therapeutics: The potential role from traditional to precision medicine[J]. Acta Pharmaceutica Sinica. B, 2023, 13 2: Pages 478-497. DOI:10.1016/j.apsb.2022.09.010.
[2] SHEJUTI RAHMAN BRISHTY. A Comprehensive Account on Recent Progress in Pharmacological Activities of Benzimidazole Derivatives.[J]. ACS Applied Energy Materials, 2021: 762807. DOI:10.3389/fphar.2021.762807.
[3] M ASHFAQ. Synthetic thioamide, benzimidazole, quinolone and derivatives with carboxylic acid and ester moieties: a strategy in the design of antituberculosis agents.[J]. Current medicinal chemistry, 2014: 911-931. DOI:10.2174/09298673113206660302.
[4] EL-ON J. Benzimidazole treatment of cystic echinococcosis[J]. Acta tropica, 2003, 85 2: Pages 243-252. DOI:10.1016/S0001-706X(02)00217-6.

Benzimidazole Upstream-Materialien And Downstream Produkte

Benzimidazol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

51-17-2, Benzimidazole Verwandte Suche:

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