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Benzimidazole

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Benzimidazole Basic information
Product Name:Benzimidazole
Synonyms:TIMTEC-BB SBB004294;N,N'-O-PHENYLENEFORMAMIDINE;1,3-BENZODIAZOLE;1H-BENZIMIDAZOLE;1H-BENZO[D]IMIDAZOLE;AKOS BBS-00004349;BENZIMIDAZOLE;1,3-Diazaindene
CAS:51-17-2
MF:C7H6N2
MW:118.14
EINECS:200-081-4
Product Categories:BENZIMIDAZOLE;Pharmaceutical Intermediates;Intermediates;Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;Imidazol&Benzimidazole;Imidaxoles;A group of systemic fungicides benzimidazoles;Pharmaceutical intermediate;51-17-2;bc0001
Mol File:51-17-2.mol
Benzimidazole Structure
Benzimidazole Chemical Properties
Melting point 169-171 °C (lit.)
Boiling point 360 °C
density 1.1151 (rough estimate)
refractive index 1.5500 (estimate)
Fp 360°C
storage temp. Store below +30°C.
solubility xylene: soluble1g in 2g (boiling)(lit.)
form Crystalline Powder or Crystals
pka5.532(at 25℃)
color Beige to brown
Water Solubility sparingly soluble
λmax271nm(MeOH)(lit.)
Merck 14,1081
BRN 109682
Stability:Stable. Combustible. Incompatible with strong oxidising agents.
Cosmetics Ingredients FunctionsNOT REPORTED
InChI1S/C7H6N2/c1-2-4-7-6(3-1)8-5-9-7/h1-5H,(H,8,9)
InChIKeyHYZJCKYKOHLVJF-UHFFFAOYSA-N
SMILESc1ccc2[nH]cnc2c1
LogP1.320
CAS DataBase Reference51-17-2(CAS DataBase Reference)
NIST Chemistry Reference1H-Benzimidazole(51-17-2)
EPA Substance Registry SystemBenzimidazole (51-17-2)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 37/39-26-24/25
WGK Germany 3
RTECS DD5425000
Hazard Note Irritant
TSCA TSCA listed
HS Code 29339990
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Hazardous Substances Data51-17-2(Hazardous Substances Data)
ToxicityLD50 oral in mouse: 2910mg/kg
MSDS Information
ProviderLanguage
Benzimidazole English
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SigmaAldrich English
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Benzimidazole Usage And Synthesis
Chemical PropertiesBenzimidazole 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.
UsesBenzimidazole 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.
DefinitionChEBI: 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.
PreparationBenzimidazole 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.
General DescriptionWhite tabular crystals.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileAn 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 HazardACUTE/CHRONIC HAZARDS: When heated to decomposition Benzimidazole emits highly toxic fumes.
Fire HazardFlash point data for Benzimidazole are not available. Benzimidazole is probably combustible.
PharmacologyThe 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.
Safety ProfilePoison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits highly toxic fumes of NOx.
Purification MethodsIt crystallises from water or aqueous EtOH (charcoal) and is dried at 100o for 12hours. [Beilstein 23 H 131, 23/6 V 196.]
References[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.
Tag:Benzimidazole(51-17-2) Related Product Information
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