2-MERCAPTO-5-NITROBENZIMIDAZOLE

2-MERCAPTO-5-NITROBENZIMIDAZOLE Property

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

Yes

HS Code 

29339900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-MERCAPTO-5-NITROBENZIMIDAZOLE Chemical Properties,Usage,Production

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