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M29800

Sigma-Aldrich

2-Methylbenzimidazole

98%

Synonym(s):

2-Methyl-1H-1,3-benzodiazole, 2-Methyl-1H-benzimidazole, 2-Methyl-1H-benzo[d]imidazole, 2-Methylbenzoimidazole

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About This Item

Empirical Formula (Hill Notation):
C8H8N2
CAS Number:
615-15-6
Molecular Weight:
132.16
Beilstein:
112264
EC Number:
210-411-9
MDL number:
MFCD00005598
UNSPSC Code:
12352100
eCl@ss:
32151902
PubChem Substance ID:
24896787
NACRES:
NA.22

Assay

98%

mp

175-177 °C (lit.)

SMILES string

Cc1nc2ccccc2[nH]1

InChI

1S/C8H8N2/c1-6-9-7-4-2-3-5-8(7)10-6/h2-5H,1H3,(H,9,10)

InChI key

LDZYRENCLPUXAX-UHFFFAOYSA-N

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Application

  • 2-Methylbenzimidazole is an important pharmacophore widely used in medicinal chemistry for the synthesis of various antibacterial and antifungal agents.
  • It can be used as a key precursor to synthesize substituted benzimidazo[1,2-a]quinolones.
  • It can be used in the synthesis of reversible solid-to-liquid phase transition coordination polymer crystals.
  • 2-Methylbenzimidazole also exhibits corrosion inhibition.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H315,H318,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis and biological evaluation of substituted benzimidazoles.
Shah K, et al.
Journal of the Indian Chemical Society, 93, 1009-1018 (2016)
Deidré van den Berg et al.
Bioorganic & medicinal chemistry, 15(11), 3692-3702 (2007-04-10)
We have recently reported that a series of (E)-8-styrylcaffeines and (E)-2-styrylbenzimidazoles are moderate to very potent competitive inhibitors of monoamine oxidase B (MAO-B). The most potent member of the series was found to be (E)-8-(3-chlorostyryl)caffeine (CSC) with an enzyme-inhibitor dissociation
Reversible solid-to-liquid phase transition of coordination polymer crystals.
Umeyama D, et al.
Journal of the American Chemical Society, 137(2), 864-870 (2015)
Synthesis and Antimicrobial Activity of Some Benzimidazole and 2-Methylbenzimidazole Derivatives.
Jain P and Tiwari M
Asian Journal of Chemistry, 29(4), 838-838 (2017)
Novel strategy for synthesis of substituted benzimidazo [1, 2-a] quinolines.
Kato J Y, et al.
Organic Letters, 15(14), 3794-3797 (2013)
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