5-Methoxy-2-mercaptobenzimidazole

Base Information

• Chemical Name: 5-Methoxy-2-mercaptobenzimidazole
• CAS No.: 37052-78-1
• Molecular Formula: C8H8N2OS
• Molecular Weight: 180.23
• Hs Code.: 29332900
• European Community (EC) Number: 253-326-2
• UNII: 143562LXX0
• DSSTox Substance ID: DTXSID20190558
• Nikkaji Number: J260.727A
• Wikidata: Q27251572
• Pharos Ligand ID: CQB1PAKKRKTC
• ChEMBL ID: CHEMBL1509639
• Mol file: 37052-78-1.mol

Synonyms:37052-78-1;5-Methoxy-2-mercaptobenzimidazole;2-Mercapto-5-methoxybenzimidazole;5-methoxy-1H-benzo[d]imidazole-2-thiol;5-Methoxy-2-benzimidazolethiol;5-methoxy-1H-benzimidazole-2-thiol;5-methoxy-1,3-dihydrobenzimidazole-2-thione;1,3-Dihydro-5-methoxy-2H-benzimidazole-2-thione;5-methoxy-1H-1,3-benzodiazole-2-thiol;2H-Benzimidazole-2-thione, 1,3-dihydro-5-methoxy-;2-MERCAPTO-5-METHOXY-1H-BENZIMIDAZOLE;MFCD00134581;5-Methoxy-1H-benzoimidazole-2-thiol;UNII-143562LXX0;EINECS 253-326-2;143562LXX0;5-methoxy-1H-benzo[d]imidazole-2(3H)-thione;EC 253-326-2;2H-Benzimidazole-2-thione, 1,3-dihydro-5-(methoxy-d3)-;5-Methoxy-1H-benzo[d]imidazole-2-thiol;5-METHOXY-1H-BENZO(D)IMIDAZOLE-2(3H)-THIONE;Maybridge1_006266;Omeprazole EP Impurity A;5-methoxy-1,3-dihydro-2H-benzimidazole-2-thione;5-methoxy-2benzimidazolethiol;MLS000083176;5-Methoxy-2-benzimidazolthiol;SCHEMBL916531;CHEMBL1509639;SCHEMBL16198394;HMS559E18;2-Mercapto-5-methoxy-1H-benzim;6-methoxy-2-mercaptobenzimidazole;DTXSID20190558;2-mercapto-5-methoxybenzoimidazole;HMS2298P11;2-mercapto-5-methoxy benzimidazole;BCP04509;5 -methoxy-2 -mercaptobenzimidazole;CCG-42938;STK506487;STK802141;6-Methoxy-1H-benzoimidazole-2-thiol;5-Methoxy-2-benzimidazolethiol, 99%;AKOS000120845;AKOS002657565;AKOS023552903;5-methoxy-(1H)-benzimidazole-2-thiol;5-methoxy-2-mercapto-1H-benzimidazole;AB03750;AC-6273;CCG-339969;CS-O-31075;CS-W008378;HY-W008378;PS-6231;SMR000046769;SY018610;5-METHOXY-2-THIO-1H-BENZIMIDAZOLE;5-METHOXYBENZO[D]IMIDAZOLE-2-THIOL;OMEPRAZOLE IMPURITY A [EP IMPURITY];5-methoxy-1H-benzimidazol-2-yl hydrosulfide;5-METHOXY-2-THIOHYDROXY BENZIMIDAZOLE;A6375;AM20040306;BB 0240770;FT-0612746;M1256;EN300-18300;AN-829/05700007;SR-01000534899;SR-01000534899-1;SR-01000534899-3;W-202531;OMEPRAZOLE MAGNESIUM IMPURITY A [EP IMPURITY];Q27251572;Z221604426;ETHYL3-[(1H-PYRROLE-2-CARBONYL)-AMINO]PROPIONATE

Chemical Property of 5-Methoxy-2-mercaptobenzimidazole

Chemical Property:

• Appearance/Colour: off-white to light yellowish-brown powder
• Vapor Pressure: 0.000641mmHg at 25°C
• Melting Point: 255 °C
• Refractive Index: 1.694
• Boiling Point: 309.4 °C at 760 mmHg
• PKA: 10.13±0.30(Predicted)
• Flash Point: 140.9 °C
• PSA: 72.90000
• Density: 1.38 g/cm³
• LogP: 2.23410
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Sensitive.: Air Sensitive
• Solubility.: DMSO (Slightly), Methanol (Sparingly)
• Water Solubility.: insoluble
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 180.03573406
• Heavy Atom Count: 12
• Complexity: 198

Purity/Quality:

98% ^*data from raw suppliers

5-Methoxy-2-mercaptobenzimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-37-22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)NC(=S)N2
• 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.
• Uses: Reagent used in the synthesis of COX-2 inhibitors 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. 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.

Technology Process of 5-Methoxy-2-mercaptobenzimidazole

There total 36 articles about 5-Methoxy-2-mercaptobenzimidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

carbon disulfide (75-15-0,12122-00-8) + 4-methoxy-1,2-phenylenediamine (102-51-2) → 2-Mercapto-5-methoxybenzimidazole (37052-78-1)

Guidance literature:

at 0 - 60 ℃; Temperature; Cooling with ice;

Reference yield: 91.0%

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

Guidance literature:

In ethanol; water; for 8h; Heating;

DOI:10.1248/cpb.37.1517

Reference yield: 90.0%

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

Guidance literature:

In N,N-dimethyl-formamide; for 0.05h; Temperature; Time; Microwave irradiation;

upstream raw materials:

potassium ethyl xanthogenate

4-methoxy-1,2-phenylenediamine

carbon disulfide

omeprazole

Downstream raw materials:

<(5-methoxy-2-benzimidazolyl)thio>acetic acid

1-(4-bromo-phenyl)-2-(5-methoxy-1H-benzoimidazol-2-ylsulfanyl)-ethanol

1-(4-chloro-3-methyl-phenyl)-2-(5-methoxy-1H-benzoimidazol-2-ylsulfanyl)-ethanol

1-(4-bromo-phenyl)-2-(5-methoxy-1H-benzoimidazole-2-sulfonyl)-ethanol

Refernces

• 1、 Sever, Belgin,Akal?n ?ift?i, Gül?en,Alt?ntop, Mehlika Dilek. "A new series of benzoxazole-based SIRT1 modulators for targeted therapy of non-small-cell lung cancer". . . Retrieved 2020/09/21.
• 2、 Halder, Atreyee,Mahanty, Kingshuk,Maiti, Debabrata,De Sarkar, Suman. "Highly Diastereoselective Synthesis of Dihydro-benzoimidazo-[1,3]-thiazines via Electro-oxidative Selenocyclization of Thioallyl Benzoimidazoles". supporting information. p. 3895 - 3899. Retrieved 2021/10/23.