583-39-1

Basic information

• Product Name: 2-Mercaptobenzimidazole
• Synonyms: 1H-BenziMidazol-2-thiol;Lansoprazole EP IMpurity E;1H-benzo[d]iMidazole-2(3H)-thione;2-Mercapto-1H-benzimidazole, 2-Sulphanyl-1H-benzimidazole;Rabeprazole Related CoMpound C;2-MercaptobenziMidazole, 98.0%(T);2 - Mercapto benzene and iMidazole;2-Mercaptobenzimidazole, MBI
• CAS NO: 583-39-1
• Molecular Formula: C₇H₆N₂S
• Molecular Weight: 150.2
• EINECS: 209-502-6
• Product Categories: Pyridines;Rubber Chemicals;BENZIMIDAZOLE;Industrial/Fine Chemicals;PHARMACEUTICAL INTERMEDIATES;Organics;Imidazole;Imidazoles;Intermediates of Rabeprazole;Aromatics;Heterocycles;Miscellaneous Reagents;Sulfur & Selenium Compounds
• Mol File: 583-39-1.mol
• Article Data: 51

Chemical Properties

• Melting Point: 300-304 °C(lit.)
• Boiling Point: 270.6 °C at 760 mmHg
• Flash Point: >250°C
• Appearance: White to beige/Powder
• Density: 1.42
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: 0.3g/l
• PKA: 10.24±0.10(Predicted)
• Water Solubility: <0.1 g/100 mL at 23.5℃
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,1082
• BRN: 119867
• CAS DataBase Reference: 2-Mercaptobenzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Mercaptobenzimidazole(583-39-1)
• EPA Substance Registry System: 2-Mercaptobenzimidazole(583-39-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36-24/25
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 2
• RTECS: DE1050000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 583-39-1(Hazardous Substances Data)

Usage

Chemical Description

2-mercaptobenzimidazole is a heterocyclic compound containing a benzimidazole ring and a thiol group.

Description

2-Mercaptobenzimidazole is a very useful corrosion inhibitor and cleaner. It can be used to remove the mercury (II) from aqueous solutions and chlor-alkali industry wastewater1. It can be added to the surface film to inhibit the corrosion of metals like copper2-3 and mild steel4. It can also be used as the carrier for the coated-wire mercury (II)-selective electrodes5. 2-Mercaptobenzimidazole is also used as an anti-degradant. It is utilized for protecting rubber from oxidation. It is also employed as an intermediate in the preparation of rabeprazole. Further, it finds application in anti-leprosy drugs in medicine6.

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/

Chemical Properties

yellow or white crystals

Uses

Different sources of media describe the Uses of 583-39-1 differently. You can refer to the following data:
1. An antidegradant, protecting rubber from oxidation. An intermediate in the synthesis of Rabeprazole (R070500)
2. 2-Mercaptobenzimidazole is used as an antidegradant. It is utilized for protecting rubber from oxidation. It is also employed as an intermediate in the preparation of rabeprazole. Further, it finds application in anti-leprosy drugs in medicine. In addition to this, it is used as a copper plating brightener.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 4, p. 569, 1963The Journal of Organic Chemistry, 29, p. 3209, 1964 DOI: 10.1021/jo01034a020

General Description

White to yellow crystals or cream colored powder. Slight odor.

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.]

InChI:InChI=1/C7H6N2S/c10-9-5-8-6-3-1-2-4-7(6)9/h1-5,10H

Synthetic route

carbon disulfide (75-15-0) + 1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
With potassium hydroxide In ethanol Heating;	95%
With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate In neat (no solvent) at 20℃; for 0.5h; Catalytic behavior; Reagent/catalyst;	93%
With Cyclohexyl isocyanide In ethanol at 20℃; for 3h;	92%

tetrachloromethane (56-23-5) + 1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
With sodium sulfide; N-benzyl-N,N,N-triethylammonium chloride In water for 8h; Ambient temperature;	95%

sodium trithiocarbonate (534-18-9) + 1,2-diamino-benzene (95-54-5) → 1-methyl-2-pyridinethione (2044-27-1) + 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
With 2-chloro-1-methyl-pyridinium iodide In dimethyl sulfoxide at 40℃; for 1h;	A 95% B 85%

Thiram (137-26-8) + 1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
In water at 110℃; Green chemistry;	93%

1,2-diamino-benzene (95-54-5) + N,N-diphenylthiourea (102-08-9) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
In N,N-dimethyl acetamide for 0.0833333h; Irradiation;	92%
With pyridine

1,2-diamino-benzene (95-54-5) + 3-methyl-1-(methyldithiocarbonyl)imidazolium iodide → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
In ethanol for 3h; Cyclization; Heating;	92%

3-phenylimino-3H-benzimidazo<2,1-c><1,2,4>-dithiazole (72885-89-3) + aniline (62-53-3) → 2,3-dihydrobenzimidazol-2-thione (583-39-1) + N,N',N''-triphenylguanidine (101-01-9)

Conditions	Yield
at 90℃; for 1h;	A 91% B 87%

5-(4-chlorophenyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione (23766-28-1) + 1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
In N,N-dimethyl acetamide for 0.133333h; Irradiation;	91%

thiourea (17356-08-0) + 1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
Irradiation; microwave;	90%
In N,N-dimethyl acetamide for 0.0333333h; Irradiation;	82%
With PPA for 0.133333h; Irradiation;	71%

Triphenylphosphonio-thiobenzimidazolat → 2,3-dihydrobenzimidazol-2-thione (583-39-1) + Triphenylphosphine oxide (791-28-6)

Conditions	Yield
In diethyl ether; water	A 87% B 83%

potassium thioacyanate (333-20-0) + 1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
With hydrogenchloride In water at 80℃; for 24h; Green chemistry;	87%

phenyl isothiocyanate (103-72-0) + 1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
With acetic acid In N,N-dimethyl acetamide for 0.183333h; Irradiation;	86%
With tris(bis(trimethylsilyl)amido)lanthanum(III) In toluene at 80℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction;	86%

benzylamine (100-46-9) + 2-phenyl-2,3-dihydro-4H- [1,3]thiazino[3,2-a]benzimidazol-4-one (326007-50-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1) + (E)-N-benzylcinnamamide (57152-94-0, 104047-17-8, 5100-00-5)

Conditions	Yield
In ethanol for 1h; Heating;	A n/a B 83%

3-(2-benzimidazolylthio)-1,4-dioxo-1,4-diphenyl-2-butene (103742-59-2) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
With hydrazine hydrate In methanol Heating;	80%

benzylamine (100-46-9) + 2-(4-methoxy-phenyl)-2,3-dihydro-1-thia-4a,9-diaza-fluoren-4-one (326881-96-3) → 2,3-dihydrobenzimidazol-2-thione (583-39-1) + (E)-3-(4-methoxyphenyl)-N-phenylmethyl-2-propenamide (612095-65-5)

Conditions	Yield
In ethanol for 1h; Heating;	A n/a B 76%

1H-imidazole-1-carbodithioic acid methyl ester (74734-11-5) + 1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
In ethanol for 5h; Cyclization; Heating;	74%

1,2-diamino-benzene (95-54-5) + sodium dimethyldithiocarbamate (128-04-1) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
With aluminum (III) chloride In water; N,N-dimethyl-formamide at 120℃; for 0.5h;	73%

tert-butyl isothiocyanate (590-42-1) + 1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
With tris(bis(trimethylsilyl)amido)lanthanum(III) In toluene at 80℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction;	71%

thiosemicarbazide (79-19-6) + 1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
at 180 - 190℃; for 1h;	69%
at 180 - 190℃;	45%

trifluoromethane sulfonyl chloride (421-83-0) + 1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
With triphenylphosphine; sodium iodide In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;	69%

phenylene-1,2-diisothiocyanate (71105-17-4) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
With isopropylamine In acetonitrile for 0.2h; Ambient temperature;	68%

3-(2-benzimidazolylthio)-1-oxo-1-phenyl-2-propene (103742-55-8) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
With hydrazine hydrate In methanol for 3h; Heating;	67%

potassium ethyl xanthogenate (140-89-6) + 1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
In ethanol; water at 80℃; Reflux;	65%
In ethanol; water	60%
With ethanol; water

dimethyl sulfoxide (67-68-5) + 1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
With potassium sulfide at 140℃; for 24h; Sealed tube; Schlenk technique; Inert atmosphere;	65%

ammonium thiocyanate + 1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
In neat (no solvent) for 1h; Milling; Green chemistry;	64%

N1,N2-bis[N-phenylthiocarbamoyl]-1,2-diaminobenzene (50521-79-4) → 2,3-dihydrobenzimidazol-2-thione (583-39-1) + N,N-diphenylthiourea (102-08-9)

Conditions	Yield
for 0.116667h; Irradiation; microwave;	A 60% B 10%

[1,3]thiazino[3,2-a]benzimidazol-4-one (19950-81-3) + benzylamine (100-46-9) → 1,3-di(N-benzylcarbamoylethyl)-2,3-dihydro-1H-benz[d]imidazole-2-thione + 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
at 184℃; for 1h;	A 58% B 30%

1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
With sulfur; 2,2‐difluoro‐2‐(triphenylphosphonio)acetate at 80℃; for 0.0833333h; Inert atmosphere; Sealed tube;	56%

chloroform (67-66-3) + 1,2-diamino-benzene (95-54-5) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
With sulfur; potassium tert-butylate In 1,4-dioxane; 2-ethoxy-ethanol at 0℃; for 16h;	53%

1-aminobenzimidazole (6299-92-9) → 2,3-dihydrobenzimidazol-2-thione (583-39-1)

Conditions	Yield
With sulfur a) from 165 to 170 deg C, 15 min, b) from 295 to 300 deg C, 1 h;	50%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + benzyl bromide (100-39-0) → 1-benzyl-2-(benzylthio)-1H-benzo-[d]-imidazole (87216-52-2)

Conditions	Yield
With sodium naphthalenide In tetrahydrofuran for 3h; Ambient temperature;	100%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + ethyl iodide (75-03-6) → 1-ethyl-2-(ethylthio)-1H-benzo[d]imidazole (124530-66-1)

Conditions	Yield
With sodium naphthalenide In tetrahydrofuran for 5h; Ambient temperature;	100%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + 1-iodo-propane (107-08-4) → 1-Propyl-2-propylsulfanyl-1H-benzoimidazole (124530-67-2)

Conditions	Yield
With sodium naphthalenide In tetrahydrofuran for 7h; Ambient temperature;	100%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + allyl bromide (106-95-6) → 1,2-diallyl sulfanyl-1H-benzoimidazole (124530-69-4)

Conditions	Yield
With sodium naphthalenide In tetrahydrofuran for 5h; Ambient temperature;	100%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + [1-bromo-1-(1,1,2,2-tetrafluoroethoxy)methyl]phenylketone (1369761-90-9) → 3-phenyl-2-(1,1,2,2-tetrafluoroethoxy)-2,3-dihydrobenzo[4,5]imidazo[2,1-b]thiazol-3-ol (1369762-01-5)

Conditions	Yield
In 1,4-dioxane at 90℃; for 18h; Hantzsch type cyclization;	100%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + 3-(4-nitrophenyl)oxirane-2,2-dicarbonitrile (34559-52-9) → 2-(4-nitrophenyl)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one (80815-13-0)

Conditions	Yield
In acetone for 48h; Ambient temperature;	99%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + formaldehyd (50-00-0) → 1,3-di(hydroxymethyl)-2,3-dihydro-1H-benzo[d]imidazole-2-thione (6028-35-9)

Conditions	Yield
In ethanol; water for 0.166667h; hydroxymethylation; Heating; ultrasound irradiation;	98%
In ethanol for 0.5h; Alkylation; Heating;	92%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + 3,5-di-tert-butyl-4-hydroxybenzyl acetate (14387-17-8) → 2-[(3,5-di(tert-butyl)-4-hydroxybenzyl)sulfanyl]-1H-benzimidazole

Conditions	Yield
With formic acid In acetone at 20℃; for 48h; Temperature;	98%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + 3,4-(methylenedioxy)-benzeneboronic acid (94839-07-3) → 1-(benzo[d][1,3]dioxol-5-yl)-1H-benzo[d]imidazole

Conditions	Yield
With copper(II) acetate monohydrate; sodium hydrogencarbonate In dimethyl sulfoxide at 100℃; Chan-Lam Coupling; chemoselective reaction;	98%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + methyl iodide (74-88-4) → 2-methylsulfanylbenzimidazole (7152-24-1)

Conditions	Yield
With triethylamine In tetrahydrofuran	97%
With ethanol
With sodium hydroxide
With SeH(1-) 1.) methanol, reflux, 2) ethanol, room temp., overnight;
With potassium carbonate In acetonitrile at 20℃; for 16h;

2,3-dihydrobenzimidazol-2-thione (583-39-1) + 4-Hydroxy-4-methyl-oct-2-ynenitrile (108940-34-7) → 2-(2-Imino-2H-1-thia-4a,9-diaza-fluoren-4-yl)-hexan-2-ol (108940-35-8)

Conditions	Yield
With lithium hydroxide In 1,4-dioxane	97%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + methyl iodide (74-88-4) → 1-methyl-2-(methylthio)-1H-benzimidazole (4344-61-0)

Conditions	Yield
With sodium naphthalenide In tetrahydrofuran for 3h; Ambient temperature;	97%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + acetic anhydride (108-24-7) → 1-(2-thioxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)ethanone (21541-32-2)

Conditions	Yield
at 110 - 115℃; for 0.5h;	97%
for 3h; Reflux;	94%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + phenyl propargyl ketone (3623-15-2) → 3-(2-benzimidazolylthio)-1-oxo-1-phenyl-2-propene (103742-55-8)

Conditions	Yield
In methanol for 3h; Heating;	96%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + 3,5-di-tert-butyl-4-hydroxybenzyl acetate (14387-17-8) → 1,3-bis(3,5-di(tert-butyl)-4-hydroxybenzyl)-1,3-dihydrobenzimidazole-2-thione (54114-47-5)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 24h; Temperature;	96%

methanol (67-56-1) + 2,3-dihydrobenzimidazol-2-thione (583-39-1) → 2-methylsulfanylbenzimidazole (7152-24-1)

Conditions	Yield
With hydrogenchloride for 2h; Heating;	95%
With hydrogenchloride for 2h; Heating;	95%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + allyl methyl carbonate (35466-83-2) → 1-allyl-1,3-dihydro-2H-benzo[d]imidazole-2-thione (87216-53-3)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 25℃; for 3h;	95%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + phenylacetylene (536-74-3) → (Z)-2-(2-phenylethenylthio)-1H-benzimidazole

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide for 4h; Heating;	95%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + 4-ethylphenylboronic acid (63139-21-9) → 2-((4-ethylphenyl)thio)-1H-benzo[d]imidazole (5315-67-3)

Conditions	Yield
With [2,2]bipyridinyl; copper(II) acetate monohydrate In water; N,N-dimethyl-formamide at 80℃; Chan-Lam Coupling; chemoselective reaction;	95%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + phenylboronic acid (98-80-6) → 2-(phenylsulfanyl)-1H-benzimidazole (2360-29-4)

Conditions	Yield
With [2,2]bipyridinyl; copper(II) acetate monohydrate In water; N,N-dimethyl-formamide at 80℃; Solvent; Chan-Lam Coupling; chemoselective reaction;	95%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + mercury(II) iodide → HgI2(benzo-1,3-imidazole-2-thione) (405063-60-7)

Conditions	Yield
In methanol soln. of stoich. amt. of org. compd. added dropwise to soln. of Hg compd.; after few d filtered, washed with cold MeOH, dried in air, elem. anal.;	94%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + ethyl bromide (74-96-4) → 2-(ethylsulfanyl)-1H-benzimidazole (14610-11-8)

Conditions	Yield
With sodium hydroxide In isopropyl alcohol at 40℃; for 1h; Cooling;	94%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + benzyl chloride (100-44-7) → 2-(benzylthio)-1H-benzo[d]imidazole (51290-77-8)

Conditions	Yield
With potassium carbonate In acetone for 3h; Reflux;	93%

2,3-dihydrobenzimidazol-2-thione (583-39-1) → benzoimidazole (51-17-2)

Conditions	Yield
With dihydrogen peroxide; acetic acid at 25℃; for 0.0166667h;	93%
With sodium tetrahydroborate; nickel dichloride In methanol at 20℃; for 0.0833333h;	84%
With sodium hydrogencarbonate In dimethyl sulfoxide at 100℃; for 20h;	30%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + 4-methylphenylboronic acid (5720-05-8) → 2-[(4-methylphenyl)sulfanyl]-1H-benzimidazole (4946-28-5)

Conditions	Yield
With [2,2]bipyridinyl; copper(II) acetate monohydrate In water; N,N-dimethyl-formamide at 80℃; Chan-Lam Coupling; chemoselective reaction;	93%

2,3-dihydrobenzimidazol-2-thione (583-39-1) + 3,4-dimethyl phenylboronic acid (55499-43-9) → 1-(3,4-dimethylphenyl)-2-((3,4-dimethylphenyl)thio)-1H-benzo[d]imidazole

Conditions	Yield
With [2,2]bipyridinyl; copper(II) acetate monohydrate In N,N-dimethyl-formamide at 30℃; Chan-Lam Coupling; chemoselective reaction;	93%

Upstream product

• 51290-77-8 2-(benzylthio)-1H-benzo[d]imidazole 
• 333-20-0 potassium thioacyanate 
• 39145-59-0 o-phenylenediamine hydrochloride 
• 17356-08-0 thiourea 
• 1155-37-9 bis-benzimidazole disulfide 
• 103742-55-8 3-(2-benzimidazolylthio)-1-oxo-1-phenyl-2-propene 
• 103-72-0 phenyl isothiocyanate 
• 95-54-5 1,2-diamino-benzene 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 23766-28-1 5-(4-chlorophenyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione 
• 6028-35-9 1,3-di(hydroxymethyl)-2,3-dihydro-1H-benzo[d]imidazole-2-thione 
• 58536-65-5 1-vinylbenzimidazole-2-thione 
• 75-15-0 carbon disulfide 
• 39222-69-0 3-[(2-aminophenyl)amino]-5,5-dimethylcyclohex-2-en-1-one 

Downstream Products

• 7152-24-1 2-methylsulfanylbenzimidazole 
• 4344-61-0 1-methyl-2-(methylthio)-1H-benzimidazole 
• 3418-46-0 1,3-dimethyl-1,3-dihydro-benzoimidazole-2-thione 
• 526197-35-3 2,3-bis-phenylhydrazono-2,3,4,5-tetrahydrothiazolo[3,2-a]benzimidazole 
• 326881-96-3 2-(4-methoxy-phenyl)-2,3-dihydro-1-thia-4a,9-diaza-fluoren-4-one 
• 326007-50-5 2-phenyl-2,3-dihydro-4H- [1,3]thiazino[3,2-a]benzimidazol-4-one 
• 51290-77-8 2-(benzylthio)-1H-benzo[d]imidazole 
• 68470-82-6 methyl 2-oxo-2H-thiazino[3,2-a]benzimidazole-4-carboxylate 
• 123157-45-9 bis(triphenylphosphine)(benz-1,3-imidazoline-2-thione)copper(I) nitrate 
• 136407-64-2 C₄₃H₃₆ClCuN₂P₂S 

Relevant articles and documents

A new strategy for the synthesis of 2-mercaptobenzazole derivatives by green chemistry metrics

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

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Synthesis Of di- and tri-substituted thiourea derivatives in water using choline chloride–urea catalyst

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.