2-MERCAPTO-5-NITROBENZIMIDAZOLE Chemical Properties

Melting point:

274 °C (dec.) (lit.)

Boiling point:

348.4±44.0 °C(Predicted)

Density 

1.4666 (rough estimate)

refractive index 

1.6740 (estimate)

storage temp. 

-20°C Freezer, Under inert atmosphere

solubility 

1 M NaOH: soluble50mg/mL, opaque, dark red

pka

9.22±0.30(Predicted)

form 

Solid

color 

Light Yellow to Light Orange

BRN 

172127

InChI

InChI=1S/C7H5N3O2S/c11-10(12)4-1-2-5-6(3-4)9-7(13)8-5/h1-3H,(H2,8,9,13)

InChIKey

YPXQSGWOGQPLQO-UHFFFAOYSA-N

SMILES

C1(=S)NC2=CC=C([N+]([O-])=O)C=C2N1

CAS DataBase Reference

6325-91-3(CAS DataBase Reference)

EPA Substance Registry System

2H-Benzimidazole-2-thione, 1,3-dihydro-5-nitro- (6325-91-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

Yes

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-MERCAPTO-5-NITROBENZIMIDAZOLE Usage And Synthesis

Chemical Properties

yellow-brown crystalline powder

Uses

2-Mercapto-5-nitrobenzimidazole is useful for treating giardiasis. Antigiardial drug.

General Description

2-Mercapto-5-nitrobenzimidazole (MNB) is a charge transfer molecule and its influence on SiO₂ and Au electrode on pentacene organic thin film transistors has been investigated. The treatment of the Au electrodes of an organic bottom-contact thin film transistor with MNB, improves the current-voltage characteristics.

Synthesis

GENERAL METHOD: 4-Nitro-o-phenylenediamine (0.019 mol) and water (3 mL) were sequentially added to a mixed solution containing sodium hydroxide (0.022 mol), methanol (20 mL) and carbon disulfide (0.022 mol). The reaction mixture was heated to reflux for 3 hours. Subsequently, activated carbon was added cautiously and reflux was continued for 10 minutes before the activated carbon was removed by thermal filtration. The filtrate was heated to 60-70 °C and the reaction was quenched with water (20 mL) preheated to 70 °C, followed by the slow addition of 50% acetic acid solution (9 mL) under vigorous stirring. The reaction solution was cooled in a refrigerator for 3 h to promote crystallization, and the target product 2-mercapto-5-nitrobenzimidazole was finally isolated.

References

[1] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 696 - 701
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 19, p. 6317 - 6326
[3] ACS Combinatorial Science, 2017, vol. 19, # 12, p. 738 - 747
[4] Journal of the Indian Chemical Society, 1984, vol. 61, # 1, p. 89 - 91
[5] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 19, p. 5550 - 5559

2-MERCAPTO-5-NITROBENZIMIDAZOLE(6325-91-3)Related Product Information

• 2-MERCAPTO-5-NITROBENZIMIDAZOLE
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• ZERENEX E/5051468
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• 2-(5-NITRO-1H-BENZOIMIDAZOL-2-YLSULFANYL)-PROPIONIC ACID
• [(5-NITRO-1-PHENYL-1H-BENZIMIDAZOL-2-YL)THIO]ACETIC ACID
• [(5-NITRO-1H-BENZIMIDAZOL-2-YL)THIO]ACETIC ACID
• 2-(5-NITRO-1H-BENZOIMIDAZOL-2-YLSULFANYL)-ACETAMIDE
• 5-NITRO-1-[3-(TRIFLUOROMETHYL)PHENYL]-1H-BENZIMIDAZOLE-2-THIOL