2-Mercapto-5-nitrobenzimidazole

Product Name2-Mercapto-5-nitrobenzimidazole
CAS6325-91-3
MFC7H5N3O2S
MW195.2
EINECS
MOL File6325-91-3.mol

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	TSCA listed
HS Code	29339900
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

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

75-15-0

99-56-9

6325-91-3

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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