| Identification | More | [Name]
Benzimidazole | [CAS]
51-17-2 | [Synonyms]
1,3-BENZODIAZOLE
1H-BENZIMIDAZOLE
1H-BENZO[D]IMIDAZOLE
AKOS BBS-00004349
BENZIMIDAZOLE
N,N'-O-PHENYLENEFORMAMIDINE
TIMTEC-BB SBB004294
1,3-Diazaindene
1H-Benzoimidazole
3-Azaindole
Azindole
Benziminazole
Benzoglyoxaline
Benzoimidazole
BZI
n,n’-methenyl-o-phenylenediamine
N,N'-Methenyl-o-Phenylenediamine
NSC 759
nsc759
o-Benzimidazole | [EINECS(EC#)]
200-081-4 | [Molecular Formula]
C7H6N2 | [MDL Number]
MFCD00005585 | [Molecular Weight]
118.14 | [MOL File]
51-17-2.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystals | [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 | [pka]
5.532(at 25℃) | [color ]
Beige to brown | [Stability:]
Stable. Combustible. Incompatible with strong oxidising agents. | [Water Solubility ]
sparingly soluble | [λmax]
271nm(MeOH)(lit.) | [Detection Methods]
HPLC,NMR | [Merck ]
14,1081 | [BRN ]
109682 | [InChIKey]
HYZJCKYKOHLVJF-UHFFFAOYSA-N | [LogP]
1.320 | [CAS DataBase Reference]
51-17-2(CAS DataBase Reference) | [NIST Chemistry Reference]
1H-Benzimidazole(51-17-2) | [EPA Substance Registry System]
51-17-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
DD5425000
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29339990 | [Safety Profile]
Poison by intravenous
and intraperitoneal routes. Moderately toxic
by ingestion. Mutation data reported. When
heated to decomposition it emits highly
toxic fumes of NOx. | [Hazardous Substances Data]
51-17-2(Hazardous Substances Data) | [Toxicity]
LD50 oral in mouse: 2910mg/kg |
| Hazard Information | Back Directory | [General Description]
White tabular crystals. | [Reactivity Profile]
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. | [Air & Water Reactions]
Insoluble in water. | [Health Hazard]
ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits highly toxic fumes. | [Fire Hazard]
Flash point data for this chemical are not available. BENZIMIDAZOLE(51-17-2) is probably combustible. | [Chemical Properties]
white crystals | [Uses]
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. | [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. | [Preparation]
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. | [Pharmacology]
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. | [storage]
Store at -20°C | [Purification Methods]
It 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. |
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