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M3205

Sigma-Aldrich

2-Mercaptobenzimidazole

98%

Synonym(s):

1,3-Dihydro-2H-benzimidazole-2-thione, 2-Benzimidazolethiol

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About This Item

Empirical Formula (Hill Notation):
C7H6N2S
CAS Number:
583-39-1
Molecular Weight:
150.20
Beilstein:
119867
EC Number:
209-502-6
MDL number:
MFCD00466107
UNSPSC Code:
12352100
PubChem Substance ID:
24896821
NACRES:
NA.22

Quality Level

200

Assay

98%

mp

300-304 °C (lit.)

SMILES string

S=C1Nc2ccccc2N1

InChI

1S/C7H6N2S/c10-7-8-5-3-1-2-4-6(5)9-7/h1-4H,(H2,8,9,10)

InChI key

YHMYGUUIMTVXNW-UHFFFAOYSA-N

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General description

2-Mercaptobenzimidazole is a good corrosion inhibitor as it reduces the corrosion rate of metals.

Application

2-Mercaptobenzimidazole can be used:
  • To prepare 2-benzimidazolylthioacetophenones by reacting with aromatic ketones, which is a key intermediate for the synthesis of thiazolo[3,2-a]benzimidazoles.
  • To synthesize S-arylated 2-mercapto-benzimidazoles via S-arylation with substituted aryl iodides using CuI and 1,10-phenanthroline.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H317,H373,H412

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 3 - Skin Sens. 1A - STOT RE 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Corrosion inhibition of zinc in phosphoric acid solution by 2-mercaptobenzimidazole
Wang L, et al.
Corrosion Science, 45(4), 677-683 (2003)
A convenient one-pot synthesis of 2-benzimidazolyl-thioacetophenones and thiazolo [3, 2-a] benzimidazoles
Sarhan AAO, et al.
Tetrahedron, 52(31), 10485-10496 (1996)
Sougata Sarkar et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(20), 6335-6342 (2012-04-05)
In the present study, surface-enhanced Raman spectra of a bifunctional Raman reporter, 2-mercaptobenzimidazole, has been found to be responsive exclusively towards Cu(2+) ions while the reporter remains anchored on the Au nanoparticle surface. Thus a specific Cu(2+)-ion-detection protocol emerges. The
M Backlund et al.
European journal of biochemistry, 261(1), 66-71 (1999-04-02)
The effect of several structurally different benzimidazole compounds on CYP1A1 expression at the transcriptional, mRNA and protein levels was investigated in the rat hepatoma H4IIE cell line. Omeprazole, thiabendazole, carbendazim, 2-mercaptobenzimidazole and 2-mercapto-5-methoxybenzimidazole caused a dose-dependent increase in CYP1A1 protein
Manuel Gadogbe et al.
Analytical and bioanalytical chemistry, 405(1), 413-422 (2012-10-25)
Determination of the true surface areas, concentrations, and particle sizes of gold nanoparticles (AuNPs) is a challenging issue due to the nanoparticle morphological irregularity, surface roughness, and size distributions. A ligand adsorption-based technique for determining AuNP surface areas in solution
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