37052-78-1

Basic information

• Product Name: 5-Methoxy-2-mercaptobenzimidazole
• Synonyms: 5-Methoxye-2-mercaplobenzinidazole;TIMTEC-BB SBB000219;5-METHOXY-1H-BENZO[D]IMIDAZOLE-2-THIOL;5-Methoxybenzimidazole-2-thiol;5-METHOXY-2-THIOBENZIMIDAZOLE;5-METHOXY-2-MERCAPTOBENZIMIDAZOLE;5-METHOXY-2-BENZIMIDAZOLETHIOL;2-MERCAPTO-5-METHOXY-1H-BENZIMIDAZOLE
• CAS NO: 37052-78-1
• Molecular Formula: C₈H₈N₂OS
• Molecular Weight: 180.23
• EINECS: 253-326-2
• Product Categories: BENZIMIDAZOLE;BUILDING BLOCKS;Imidazol&Benzimidazole;(intermediate of omeprazole);Benzimidazoles;Building Blocks;Heterocyclic Building Blocks;Aromatics;Sulfur & Selenium Compounds;OLED materials,pharm chemical,electronic
• Mol File: 37052-78-1.mol
• Article Data: 29

Chemical Properties

• Melting Point: 261-263 °C(lit.)
• Boiling Point: 309.4 °C at 760 mmHg
• Flash Point: 140.9 °C
• Appearance: Off-white to light yellow-brown/Powder
• Density: 1.2425 (rough estimate)
• Vapor Pressure: 0.000641mmHg at 25°C
• Refractive Index: 1.5690 (estimate)
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Sparingly)
• PKA: 10.13±0.30(Predicted)
• Water Solubility: insoluble
• Sensitive: Air Sensitive
• BRN: 3605123
• CAS DataBase Reference: 5-Methoxy-2-mercaptobenzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methoxy-2-mercaptobenzimidazole(37052-78-1)
• EPA Substance Registry System: 5-Methoxy-2-mercaptobenzimidazole(37052-78-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-37-22
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 37052-78-1(Hazardous Substances Data)

Usage

Description

2-Mercapto-5-methoxybenzimidazole is used in the preparation of COX-2 inhibitors. It is also employed in the preparation of compounds such as 5-methoxy-2[[(4-methoxy-3, 5-dimethyl-2-pyridinyl) methyl] sulfonyl]-1H-benzimidazole, 5-methoxy-2[[(4-methoxy-3, 5-dimethylpyridin-2-yl-1-oxide) methyl] sulfonyl]-1H-benzimidazole as well as tris[μ-1,2-bis(diphenylphosphino)ethane]-1:2κ2P:P′;1:3κ2P:P′;2:3κ2P:P′-di-μ-bromido-1:2κ4Br:Br-bromido-3κBr-tricopper(I) acetone hemisolvate. Furthermore, it acts as a hetercocyclic building block and serves as an intermediate of drug omeprazole1. Finally, it acts as an intermediate for manufacture of the anti-ulcer drug Omeprazole.

Chemical Properties

off-white to light yellowish-brown powder

Uses

Different sources of media describe the Uses of 37052-78-1 differently. You can refer to the following data:
1. Reagent used in the synthesis of COX-2 inhibitors
2. 2-Mercapto-5-methoxybenzimidazole is used in the preparation of COX-2 inhibitors. It is also employed in the preparation of compounds such as 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfonyl]-1H-benzimidazole and 5-methoxy-2-[[(4-methoxy-3,5-dimethylpyridin-2-yl-1-oxide)methyl]sulfonyl]-1H-benzimidazole. Further, it acts as a hetercocyclic building block and serves as an intermediate of drug omeprazole.
3. 5-Methoxy-2-benzimidazolethiol may be used in the preparation of compounds present as contaminants in omeprazole, such as 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfonyl]-1H-benzimidazole and 5-methoxy-2-[[(4-methoxy-3,5-dimethylpyridin-2-yl-1-oxide)methyl]sulfonyl]-1H-benzimidazole. It may be used in the synthesis of tris[μ-1,2-bis(diphenylphosphino)ethane]-1:2κ2P:P′;1:3κ2P:P′;2:3κ2P:P′-di-μ-bromido-1:2κ4Br:Br-bromido-3κBr-tricopper(I) acetone hemisolvate.

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Flammability and Explosibility

Notclassified

InChI:InChI=1/C8H8N2OS/c1-11-5-2-3-6-7(4-5)10-8(12)9-6/h2-4H,1H3,(H2,9,10,12)

Synthetic route

potassium ethyl xanthogenate (140-89-6) + 4-methoxy-1,2-phenylenediamine (102-51-2) → 2-Mercapto-5-methoxybenzimidazole (37052-78-1)

Conditions	Yield
In ethanol; water for 8h; Heating;	91%
In ethanol at 80℃;

potassium isopropylxanthate (140-92-1) + 4-methoxy-1,2-phenylenediamine (102-51-2) → 2-Mercapto-5-methoxybenzimidazole (37052-78-1)

Conditions	Yield
In N,N-dimethyl-formamide for 0.05h; Temperature; Time; Microwave irradiation;	90%

carbon disulfide (75-15-0) + 4-methoxy-1,2-phenylenediamine (102-51-2) → 2-Mercapto-5-methoxybenzimidazole (37052-78-1)

Conditions	Yield
With hydrogenchloride; potassium hydroxide In ethanol	72%
With potassium hydroxide In ethanol; water for 6h; Heating;	40%
With potassium hydroxide In ethanol for 3h; Heating;
With potassium hydroxide In ethanol for 8h; Reflux;
In ethanol at 60℃; for 5h;

4-methoxy-1,2-phenylenediamine (102-51-2) → 2-[(3,7-Dimethyl-2,6(E)-octadienyl)thio]-5-methoxy-1H-1,3-benzimidazole Monooxalate + 2-Mercapto-5-methoxybenzimidazole (37052-78-1)

Conditions	Yield
With potassium hydroxide In CS2; ethanol; water	A n/a B 63%

carbon disulfide (75-15-0) + 2'-amino-p-acetanisidide (5472-37-7) → 2-Mercapto-5-methoxybenzimidazole (37052-78-1) + 1-acetyl-5-methoxybenzimidazolethiol (84445-85-2)

Conditions	Yield
In N,N-dimethyl-formamide for 89h; Ambient temperature;	A 11.4% B 59.1%

6-methoxy-benzo[4,5]imidazo[2,1-b]thiazol-3-one (37052-80-5) → 2-Mercapto-5-methoxybenzimidazole (37052-78-1) + 2-<(5-methoxy-2-benzimidazolyl)thio>ethanol (79938-43-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 1.3h; Heating;	A 18.4% B 37.3%

4-methoxy-2-nitroacetanilide (119-81-3) → 2-Mercapto-5-methoxybenzimidazole (37052-78-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: Na2S*9H2O / 6 h / Heating 2: 40 percent / potassium hydroxide / ethanol; H2O / 6 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 99 percent / NaOH; KOH / H2O / 0.5 h / Heating 2: 96 percent / Na2S*9H2O / H2O / 6 h / Heating 3: 40 percent / potassium hydroxide / ethanol; H2O / 6 h / Heating View Scheme
Multi-step reaction with 2 steps 1: H2 / 5percent Pd/C 2: 11.4 percent / dimethylformamide / 89 h / Ambient temperature View Scheme

4-methoxyacetanilide (51-66-1) → 2-Mercapto-5-methoxybenzimidazole (37052-78-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 91 percent / nitric acid; sulfuric acid / 0 - 5 °C 2: Na2S*9H2O / 6 h / Heating 3: 40 percent / potassium hydroxide / ethanol; H2O / 6 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 91 percent / nitric acid; sulfuric acid / 0 - 5 °C 2: 99 percent / NaOH; KOH / H2O / 0.5 h / Heating 3: 96 percent / Na2S*9H2O / H2O / 6 h / Heating 4: 40 percent / potassium hydroxide / ethanol; H2O / 6 h / Heating View Scheme

4-methoxy-aniline (104-94-9) → 2-Mercapto-5-methoxybenzimidazole (37052-78-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / acetic acid / 2 h / 110 °C 2: 91 percent / nitric acid; sulfuric acid / 0 - 5 °C 3: Na2S*9H2O / 6 h / Heating 4: 40 percent / potassium hydroxide / ethanol; H2O / 6 h / Heating View Scheme
Multi-step reaction with 5 steps 1: 85 percent / acetic acid / 2 h / 110 °C 2: 91 percent / nitric acid; sulfuric acid / 0 - 5 °C 3: 99 percent / NaOH; KOH / H2O / 0.5 h / Heating 4: 96 percent / Na2S*9H2O / H2O / 6 h / Heating 5: 40 percent / potassium hydroxide / ethanol; H2O / 6 h / Heating View Scheme

4-methoxy-2-nitroaniline (96-96-8) → 2-Mercapto-5-methoxybenzimidazole (37052-78-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / Na2S*9H2O / H2O / 6 h / Heating 2: 40 percent / potassium hydroxide / ethanol; H2O / 6 h / Heating View Scheme
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol / 80 °C 2: ethanol / 80 °C View Scheme

carbon disulfide (75-15-0) + 2'-amino-p-acetanisidide (5472-37-7) → 2-Mercapto-5-methoxybenzimidazole (37052-78-1)

Conditions	Yield
Stage #1: carbon disulfide; 2'-amino-p-acetanisidide With potassium hydroxide; water In ethanol at 80 - 90℃; for 8 - 10h; Stage #2: With hydrogenchloride In ethanol; water at 10 - 15℃; Stage #3: Alkaline conditions;

4-methoxy-1,2-phenylenediamine hydrochloride (106658-14-4) → 2-Mercapto-5-methoxybenzimidazole (37052-78-1)

Conditions	Yield
With carbon disulfide; potassium hydroxide In ethanol; water; water ethanol

potassium ethyldithiocarbamate (63467-57-2) + 4-methoxy-1,2-phenylenediamine (102-51-2) → 2-Mercapto-5-methoxybenzimidazole (37052-78-1)

Conditions	Yield
Microwave irradiation;

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → omeprazole sulfide (73590-85-9)

Conditions	Yield
With tetrabutylammomium bromide; edetate disodium; sodium hydroxide In dichloromethane; water pH=10; pH-value;	100%
With sodium hydroxide at 20℃;	98%
With sodium hydroxide In methanol; water Reflux;	95.2%

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + methyl iodide (74-88-4) → 2-methylthio-5-methoxy-1H-benzimidazole (91168-31-9)

Conditions	Yield
With potassium hydroxide In ethanol; water	98.9%
With sodium hydroxide In methanol at 20℃; for 2h;	83.7%
With triethylamine

2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 5-methoxy-1H-benzimidazole (4887-80-3)

Conditions	Yield
With rose bengal; water; oxygen; sodium chloride In N,N-dimethyl-formamide at 25℃; for 48h; Irradiation; Green chemistry;	98%

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → 6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole (73590-85-9)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 80℃; for 1h; Solvent; Temperature;	97%
With sodium hydroxide In methanol; water at 55 - 65℃; for 2h; Large scale;	86%
With sodium hydrogencarbonate In ethanol Reagent/catalyst; Temperature; Solvent; Reflux; Large scale;	85.3%
With sodium hydroxide In ethanol; water Solvent; Reflux; Large scale;	81.1%
With sodium hydroxide In methanol at 50℃; for 4h; Reagent/catalyst; Temperature; Solvent;	34.1 g

2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 5-methoxy-1H-benzimidazole-2-sulfinyl chloride

Conditions	Yield
With sulfuryl dichloride; acetic acid In dichloromethane at -30 - 30℃; for 11.5h; Temperature;	96.3%
With thionyl chloride; acetic acid In dichloromethane at -30 - 30℃; for 11.5h; Temperature; Solvent;	96.3%
With thionyl chloride; acetic acid In dichloromethane at -30 - 30℃; for 11.5h; Temperature;	777.5 mg
With sulfuryl dichloride; acetic acid In dichloromethane at -30 - 30℃; for 11.5h; Temperature; Reagent/catalyst;	777.5 g

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + (chloromethyl)-4-methoxy-3,5-dimethylpyridine (84006-10-0) → omeprazole sulfide (73590-85-9)

Conditions	Yield
With potassium iodide; sodium hydroxide In ethanol at 15 - 55℃; for 0.5h; Inert atmosphere; Large scale;	95.1%
In methanol for 4h; Heating;	2.1 g

2-((4-(chloromethyl)-2-methoxyphenoxy)methyl)-4-methoxy-3,5-dimethylpyridine + 2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 2-(4-((4-methoxy-3,5-dimethylpyridin-2-yl)methoxy)-3-methoxybenzylthio)-5-methoxy-1H-benzo[d]imidazole

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 15h;	94%

2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 5-methoxy-1H-benzo[d]imidazole-2-d

Conditions	Yield
With rose bengal; water-d2; oxygen; sodium chloride In N,N-dimethyl-formamide at 25℃; for 48h; Irradiation; Green chemistry;	94%

2-((4-(chloromethyl)-2-methoxyphenoxy)methyl)-3,4-dimethoxypyridine + 2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 2-(4-((3,4-dimethoxypyridin-2-yl)methoxy)-3-methoxybenzylthio)-5-methoxy-1H-benzo[d]imidazole

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 15h;	93%

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + 3-((3,4-dimethoxyphenethyl)imino)-2-phenylacrylic acid methyl ester → C48H50N4O9S

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 80℃; for 1.5h; Inert atmosphere; regioselective reaction;	93%

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + 4-Methylbenzyl bromide (104-81-4) → 5-methoxy-2-[(4-methylbenzyl)sulfanyl]-1H-benzimidazole (309735-05-5)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 24h;	92%

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + benzoic acid (65-85-0) → 4-(6-Methoxy-1H-benzoimidazol-2-ylsulfanylmethyl)-benzoic Acid Methyl Ester Hydrobromide (503040-01-5)

Conditions	Yield
In ethyl acetate; N,N-dimethyl-formamide	91%

Methyl 4-(bromomethyl)benzoate (2417-72-3) + 2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 4-(6-Methoxy-1H-benzoimidazol-2-ylsulfanylmethyl)-benzoic Acid Methyl Ester Hydrobromide (503040-01-5)

Conditions	Yield
In ethyl acetate; N,N-dimethyl-formamide	91%
In ethyl acetate; N,N-dimethyl-formamide	91%

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + 1-(halomethyl)-3-phenoxybenzene → C21H18N2O2S (1356959-88-0)

Conditions	Yield
With sodium hydroxide In methanol; water at 70℃; for 12h;	91%

4-bromoethylbutanoate (2969-81-5) + 2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 4-(5-methoxybenzimidazole-2-ylthio)butanoate ester hydrogen bromide salt (349668-33-3)

Conditions	Yield
In ethanol; ethyl acetate	90%
In ethanol at 80℃; for 1h;	90%
In ethanol; ethyl acetate	90%

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + (R,S)-2-chloropropionic acid (598-78-7) → 2-(5-methoxy-1(3)H-benzimidazol-2-ylmercapto)-propionic acid (919467-09-7)

Conditions	Yield
With potassium hydroxide In ethanol for 6h; Reflux;	90%

4-(2,2,2-trifluoroethoxy)-2-((4-(chloromethyl)-2-methoxyphenoxy)methyl)-3-methylpyridine + 2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 2-(4-((4-(2,2,2-trifluoroethoxy)-3-methylpyridin-2-yl)methoxy)-3-methoxybenzylthio)-5-methoxy-1H-benzo[d]imidazole

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 15h;	90%

7-methyl-1H-indole (933-67-5) + 2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 2-(7-methyl-1H-indol-3-ylthio)-6-methoxy-1hbenzo[d]imidazole

Conditions	Yield
With manganese(III) triacetate dihydrate; acetic acid at 80℃; for 2h; Inert atmosphere; regioselective reaction;	90%

pleuromutilin tosylate (31716-01-5) + 2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 14-O-{[(5-methoxy-1H-benzimidazol-2-yl)sulfanyl]acetyl}mutilin

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene	90%

2-chloromethyl-3,5-dimethyl-4-methoxypyridine-N-oxide (848694-10-0) + 2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 5-methoxy-2-[[(4-methoxy-3,5-dimethylpyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzimidazole (142885-92-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	88%

1,5-dibromo-pentane (111-24-0) + 2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 1,5-bis(5-methoxyl-2-benzimidazoylthio)pentane

Conditions	Yield
	88%

2-chloro-3',4'-dihydroxyacetophenone (99-40-1) + 2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 1-(3,4-dihydroxy-phenyl)-2-(5-methoxy-1H-benzoimidazol-2-ylsulfanyl)-ethanone; hydrochloride

Conditions	Yield
In acetonitrile for 16h; Heating;	87%

4-(3-methoxypropoxy)-2-((4-(chloromethyl)-2-methoxyphenoxy)methyl)-3-methylpyridine + 2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 2-(4-((4-(3-methoxypropoxy)-3-methylpyridin-2-yl)methoxy)-3-methoxybenzylthio)-5-methoxy-1H-benzo[d]imidazole

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 15h;	87%

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + 2-chloromethyl-3,5-dimethylpyridine hydrochloride → 2-[((3,5-dimethyl-2-pyridinyl)methylthio)]-5-methoxy-1H-benzimidazole

Conditions	Yield
With sodium hydroxide In methanol at 55 - 60℃;	87%

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + 7-Chloro-4-chloromethyl-pyrrolo[1,2-a]quinoxaline (210222-77-8) → 2-[[(7-chloropyrrolo[1,2-a]quinoxalin-4-yl)methyl]thio]-5-methoxy-1H-benzimidazole (936110-42-8)

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; for 16h;	86%

C18H17Cl2FN2O4 + 2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 8-chloro-1-cyclopropyl-6-fluoro-7-(3-(2-((5-methoxy-1H-benzo[d]imidazol-2-yl)thio)acetamido)pyrrolidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions	Yield
Stage #1: 2-Mercapto-5-methoxybenzimidazole With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: C18H17Cl2FN2O4 In N,N-dimethyl-formamide at 40℃; for 4.2h;	86%

C19H18Cl2FN3O4 + 2-Mercapto-5-methoxybenzimidazole (37052-78-1) → 8-chloro-1-cyclopropyl-6-fluoro-7-(3-(2-((5-methoxy-1H-benzo[d]imidazol-2-yl)thio)acetamido)pyrrolidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions	Yield
Stage #1: 2-Mercapto-5-methoxybenzimidazole With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: C19H18Cl2FN3O4 In N,N-dimethyl-formamide at 40℃;	86%

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + 1-(halomethyl)-4-(propan-2-yl)benzene → 2-(4-isopropylbenzylthio)-5-methoxy-1H-benzo[d]imidazole (1356959-85-7)

Conditions	Yield
With sodium hydroxide In methanol; water at 70℃; for 12h;	85.8%

Upstream product

• 137-26-8 Thiram 
• 102-51-2 4-methoxy-1,2-phenylenediamine 
• 37052-80-5 6-methoxy-benzo[4,5]imidazo[2,1-b]thiazol-3-one 
• 73590-58-6 omeprazole 
• 132841-40-8 N-[4-Methoxy-2-(3-phenyl-thioureido)-phenyl]-acetamide 
• 75-15-0 carbon disulfide 
• 16133-49-6 5-methoxy-2-nitroaniline 
• 128-04-1 sodium dimethyldithiocarbamate 
• 67-66-3 chloroform 
• 73590-58-6 omeprazole 
• 140-89-6 potassium ethyl xanthogenate 
• 140-92-1 potassium isopropylxanthate 
• 63467-57-2 potassium ethyldithiocarbamate 
• 106658-14-4 4-methoxy-1,2-phenylenediamine hydrochloride 

Downstream Products

• 91168-31-9 2-methylthio-5-methoxy-1H-benzimidazole 
• 503040-01-5 4-(6-Methoxy-1H-benzoimidazol-2-ylsulfanylmethyl)-benzoic Acid Methyl Ester Hydrobromide 
• 511304-75-9 2-(benzylthio)-5-methoxy-1H-benzo[d]imidazole 
• 1424375-42-7 C₂₅H₁₉N₅O₇S 
• 1424375-46-1 C₂₄H₁₆FN₅O₆S 
• 1424375-49-4 C₂₅H₁₆N₆O₆S 
• 1424375-11-0 C₁₇H₁₂N₄O₅S 
• 1424375-00-7 2-((2,4-dinitrophenyl)sulphanyl)-5-methoxybenzimidazole 
• 73590-58-6 omeprazole 
• 356587-72-9 2-((5-methoxy-1H-benzo[d]imidazol-2-yl)thio)-N-phenylacetamide 
• 356587-79-6 2-((5-methoxy-1H-benzo[d]imidazol-2-yl)thio)-N-(o-tolyl)acetamide 
• 361184-76-1 2-((5-methoxy-1H-benzo[d]imidazol-2-yl)thio)-N-(2-chlorophenyl)acetamide 
• 356587-81-0 2-((5-methoxy-1H-benzo[d]imidazol-2-yl)thio)-N-(2-methoxyphenyl)acetamide 

Relevant articles and documents

Method for continuous-flow synthesis of 2-sulfydryl-5-methoxybenzimidazole

The invention belongs to the technical field of organic synthesis, and particularly relates to a method for continuous-flow synthesis of 2-sulfydryl-5-methoxybenzimidazole. The method comprises the following reaction steps in a continuous flow reactor: (1) subjecting 2-nitro-4-methoxyaniline to reacting with a reducing agent under the action of a catalyst to obtain a reaction solution containing 4-methoxy o-phenylenediamine; and (2) enabling the reaction solution containing the 4-methoxy o-phenylenediamine to react with carbon disulfide so as to generate the 2-sulfydryl-5-methoxybenzimidazole. According to the production process improved by a continuous flow technology in the invention, reaction time is greatly shortened, operation is simple and convenient, production efficiency is improved, and the yield and the purity of the obtained product are very high. Therefore, the method disclosed by the invention has a very good application prospect in the synthesis of 2-sulfydryl-5-methoxybenzimidazole.

Cinnamide derived pyrimidine-benzimidazole hybrids as tubulin inhibitors: Synthesis, in silico and cell growth inhibition studies

An approach in modern medicinal chemistry to discover novel bioactive compounds is by mimicking diverse complementary pharmacophores. In extension of this strategy, a new class of piperazine-linked cinnamide derivatives of benzimidazole-pyrimidine hybrids have been designed and synthesized. Their in vitro cytotoxicity profiles were explored on selected human cancer cell lines. Specifically, structural comparison of target hybrids with tubulin-DAMA-colchicine and tubulin-nocodazole complexes has exposed a deep position of benzimidazole ring into the αT5 loop. All the synthesized compounds were demonstrated modest to interesting cytotoxicity against different cancer cell lines. The utmost cytotoxicity has shown with an amine linker of benzimidazole-pyrimidine series, with specificity toward A549 (lung cancer) cell line. The most potent compound in this series was 18i, which inhibited cancer cell growth at micromolar concentrations ranging 2.21–7.29 μM. Flow cytometry studies disclosed that 18i inhibited the cells in G2/M phase of cell cycle. The potent antitumor activity of 18i resulted from enhanced microtubule disruption at a similar level as nocodazole on β-tubulin antibody, explored using immunofluorescence staining. The most active compound 18i also inhibited tubulin polymerization with an IC50 of 5.72 ± 0.51 μM. In vitro biological analysis of 18i presented apoptosis induction on A549 cells with triggering of ROS generation and loss of mitochondrial membrane potential, resulting in DNA injury. In addition, 18i displayed impairment in cellular migration and inhibited the colony formation. Notably, the safety profile of most potent compound 18i was revealed by screening against normal human pulmonary epithelial cells (L132: IC50: 69.25 ± 5.95 μM). The detailed binding interactions of 18i with tubulin was investigated by employing molecular docking, superimposition and free energy analyses. Thus remarks made in this study established that pyrimidine-benzimidazole hybrids as a new class of tubulin polymerization inhibitors with significant anticancer activity.

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.