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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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Kazue Sakemi et al.
Archives of toxicology, 76(12), 682-691 (2002-11-27)
2-Mercaptobenzimidazole (MBI), a rubber antioxidant, is known to exhibit potent thyroid toxicity in rats, whereas its methylated derivatives are much less toxic. To characterize this methyl-substituent effect on the thyroid toxicity of MBI, comparative toxicokinetic analyses have been conducted in
D M Manohar et al.
Water research, 36(6), 1609-1619 (2002-05-09)
The 2-mercaptobenzimidazole loaded natural clay was prepared for the removal of Hg(II) from aqueous media. Adsorption of the metal ions from aqueous solution as a function of solution concentration, agitation time, pH, temperature, ionic strength, particle size of the adsorbent
S-arylation of mercaptobenzimidazoles using Cu (I) catalysts-experimental and theoretical observations
Sekar R, et al.
Tetrahedron Letters, 52(26), 3347-3352 (2011)
Yuqin Li et al.
Colloids and surfaces. B, Biointerfaces, 104, 311-317 (2013-01-22)
The interaction of 2-mercaptobenzimidazole (MBI) with human serum albumin (HSA) was studied in vitro by equilibrium dialysis under normal physiological conditions. This study used fluorescence, ultraviolet-visible spectroscopy (UV-vis), Fourier transform infrared (FT-IR), circular dichroism (CD) and Raman spectroscopy, atomic force
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)
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