583-39-1 Usage
Chemical Description
2-mercaptobenzimidazole is a heterocyclic compound containing a benzimidazole ring and a thiol group.
Description
2-Mercaptobenzimidazole is a versatile organic compound known for its effectiveness as a corrosion inhibitor and cleaner. It possesses the ability to remove mercury (II) from aqueous solutions and chlor-alkali industry wastewater, while also being capable of inhibiting the corrosion of metals such as copper and mild steel. Additionally, it serves as a carrier for coated-wire mercury (II)-selective electrodes and has applications as an anti-degradant in rubber protection, an intermediate in the synthesis of rabeprazole, and in the development of anti-leprosy drugs.
Uses
Used in Water Treatment and Wastewater Management:
2-Mercaptobenzimidazole is used as a cleaner for removing mercury (II) from aqueous solutions and chlor-alkali industry wastewater, contributing to environmental protection and pollution control.
Used in Metal Corrosion Inhibition:
2-Mercaptobenzimidazole is used as a corrosion inhibitor for metals like copper and mild steel, enhancing the durability and longevity of metal structures and equipment.
Used in Electrochemistry:
2-Mercaptobenzimidazole is used as a carrier for coated-wire mercury (II)-selective electrodes, facilitating the development of sensitive and selective electrochemical sensors.
Used in Rubber Industry:
2-Mercaptobenzimidazole is used as an antidegradant, protecting rubber from oxidation and improving its overall performance and lifespan.
Used in Pharmaceutical Synthesis:
2-Mercaptobenzimidazole is used as an intermediate in the preparation of rabeprazole, a proton pump inhibitor used in the treatment of various gastrointestinal disorders.
Used in Medicine:
2-Mercaptobenzimidazole finds application in anti-leprosy drugs, aiding in the treatment and management of leprosy, a chronic infectious disease.
Used in Copper Plating:
2-Mercaptobenzimidazole is used as a brightener in copper plating processes, enhancing the appearance and quality of copper-coated surfaces.
Reference
Manohar, D. M., K. A. Krishnan, and T. S. Anirudhan. "Removal of mercury (II) from aqueous solutions and chlor-alkali industry wastewater using 2-mercaptobenzimidazole-clay." Water Research 36.6(2002):1609.
Chadwick, D., and T. Hashemi. "Electron spectroscopy of corrosion inhibitors: Surface films formed by 2-mercaptobenzothiazole and 2-mercaptobenzimidazole on copper." Surface Science 89.1(1979):649-659.
Trachli, B., et al. "Protective effect of electropolymerized 2-mercaptobenzimidazole upon copper corrosion." Progress in Organic Coatings 44.1(2002):17-23.
Wang, Lin. "Evaluation of 2-mercaptobenzimidazole as corrosion inhibitor for mild steel in phosphoric acid." Corrosion Science 43.12(2001):2281-2289.
Mazloum, M, M. K. Amini, and I. Mohammadpoor-Baltork. "Mercury selective membrane electrodes using 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, and hexathiacyclooctadecane carriers." Sensors & Actuators B Chemical 63.1(2000):80-85.
https://www.alfa.com/en/catalog/A18350/
Synthesis Reference(s)
Organic Syntheses, Coll. Vol. 4, p. 569, 1963The Journal of Organic Chemistry, 29, p. 3209, 1964 DOI: 10.1021/jo01034a020
Air & Water Reactions
Dust explosion: 0.140 oz/ft3. Insoluble in water. 2-Mercaptobenzimidazole is moisture sensitive. .
Reactivity Profile
An organosulfide and an amine. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Fire Hazard
Flash point data for 2-Mercaptobenzimidazole are not available; however, 2-Mercaptobenzimidazole is probably combustible.
Flammability and Explosibility
Nonflammable
Safety Profile
Poison by
intraperitoneal and intravenous routes.
Moderately toxic by ingestion. Skin and eye
irritant. When heated to decomposition it
emits toxic fumes of SO, and NO,. See also
MERCAPTANS.
Purification Methods
Crystallise it from aqueous EtOH, AcOH or aqueous ammonia. It complexes with many metals. [Brown J Chem Soc 1976 1958, Beilstein 24 II 65, 24 III/IV 287.]
Check Digit Verification of cas no
The CAS Registry Mumber 583-39-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 3 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 583-39:
(5*5)+(4*8)+(3*3)+(2*3)+(1*9)=81
81 % 10 = 1
So 583-39-1 is a valid CAS Registry Number.
InChI:InChI=1/C7H6N2S/c10-9-5-8-6-3-1-2-4-7(6)9/h1-5,10H
583-39-1Relevant articles and documents
A new strategy for the synthesis of 2-mercaptobenzazole derivatives by green chemistry metrics
Vessally, Esmail,Monfared, Aazam,Eskandari, Zahra,Abdoli, Morteza,Hosseinian, Akram
supporting information, p. 1 - 5 (2020/08/25)
A green and efficient method has been developed for the synthesis of 2-mercaptobenzazole derivatives via the reaction of commercially available aniline derivatives with low-cost and nontoxic potassium thiocyanate in water. The reactions proceeded smoothly under catalyst- and ligand-free conditions to give the corresponding products in good to excellent yields. The versatility, low cost, and environmental friendliness, in combination with high yields and easy work-up makes the procedure noteworthy.
A Highly Efficient Synthesis of 2-Benzimidazolthiones and Their Congeners under Mild Conditions
Li, Wei-wei,Zheng, Hui
, p. 175 - 181 (2019/04/17)
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Synthesis Of di- and tri-substituted thiourea derivatives in water using choline chloride–urea catalyst
Tavakol, Hossein,Mahmoudi, Amir,Ranjbari, Mohammad-Amin
, p. 113 - 123 (2018/10/24)
In this work, di- and tri-substituted thiourea derivatives have been synthesized via a one-pot, three-component reaction from carbon disulfide and aliphatic or aromatic amines using choline chloride-urea deep eutectic solvent as a catalyst in water. Both cyclic and acyclic thiourea derivatives with two or three substituents were synthesized successfully. The reactions were done at 25–100°C, using 5–20 mol% catalyst, in 3–5 h and the GC-Mass yields were between 60% and 95%. All products were characterized using FT-IR, 1H-NMR, 13C-NMR, GC-MS and melting point analyses. The results showed that both water and the DES have important effects on the yield and the rate of this reaction and both of them are necessary to obtain higher yields in less time. The extra experiment, which was designed to study the mechanism of the reaction, showed that an isothiocyanate intermediate was formed in the reaction. Finally, the results showed that by the increase of the amine's nucleophilicity, the reaction occurs faster and gives higher yield.