19190-68-2

Basic information

• Product Name: 4-METHYLBENZIMIDAZOLONE
• Synonyms: 4-METHYLBENZIMIDAZOLONE;2H-Benzimidazol-2-one,1,3-dihydro-4-methyl-(9CI);4-Methyl-1H-benzo[d]imidazol-2(3H)-one;4-Methylbenzoimidazol-2(3H)-one;4-Methyl-1,3-dihydro-2H-benzimidazol-2-one;1,3-dihydro-4-methyl-2H-Benzimidazol-2-one;4-Methyl-1,3-dihydro-benzoimidazol-2-one
• CAS NO: 19190-68-2
• Molecular Formula: C₈H₈N₂O
• Molecular Weight: 148.16
• Product Categories: BENZIMIDAZOLE
• Mol File: 19190-68-2.mol

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 143.3±10.0 °C(Predicted)
• Appearance: /
• Density: 1.201±0.06 g/cm3(Predicted)
• PKA: 12.26±0.30(Predicted)
• CAS DataBase Reference: 4-METHYLBENZIMIDAZOLONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYLBENZIMIDAZOLONE(19190-68-2)
• EPA Substance Registry System: 4-METHYLBENZIMIDAZOLONE(19190-68-2)

Safety Data

• Hazardous Substances Data: 19190-68-2(Hazardous Substances Data)

Usage

Uses

Used in Printing and Textile Industries:
4-Methylbenzimidazolone is used as a colorant for its exceptional color strength and fastness properties, making it ideal for the production of inks, dyes, and pigments in the printing and textile sectors.
Used in Pharmaceutical and Agrochemical Industries:
4-METHYLBENZIMIDAZOLONE is also utilized in the synthesis of pharmaceuticals and agrochemicals, contributing to the development of new drugs and agricultural products.
Safety Precautions:
It is crucial to handle 4-methylbenzimidazolone with care due to its potential to cause skin and eye irritation. It should be stored in a cool, dry place, away from sources of ignition to prevent any hazardous incidents.

Upstream product

• 530-62-1 1,1'-carbonyldiimidazole 
• 2687-25-4 3-methyl-1,2-benzenediamine 
• 601-87-6 3-methyl-2-nitroaniline 
• 57-13-6 urea 
• 124-38-9 carbon dioxide 
• 201230-82-2 carbon monoxide 
• 144167-54-4 1-(N-carbethoxyimidoyl)-4-methyl-2-benzimidazolone 
• 75-44-5 phosgene 

Downstream Products

• 15965-57-8 2-Chloro-4-methylbenzimidazole 
• 554-68-7 triethylamine hydrochloride 
• 14400-52-3 1,3-bis-(dichloro-fluoro-methylsulfanyl)-4-methyl-1,3-dihydro-benzoimidazol-2-one 
• 1453097-14-7 3-methyl-1-(4-methyl-1H-benzimidazol-2-yl)-4-(phenylmethyl)-1H-pyrazol-5-ol 

Relevant articles and documents

Method for preparing carbonyl heterocyclic compound

The invention provides a method for preparing a carbonyl heterocyclic compound, wherein Lewis base and hydrosilane are used as accelerators and can efficiently enable an ortho-substituted aniline compound to react with normal-pressure CO2 to generate corresponding carbonyl heterocyclic compounds containing different functional groups under mild conditions (100 DEG C, digital). According to the method, normal-pressure CO2 is used as an environmentally-friendly non-toxic carbonylation reagent, and cheap Lewis base and PMHS (industrial silicon waste) are used as accelerators, so that the use of CO, high-pressure CO2 and noble metal catalysts is avoided, the intermediate isocyanate does not need to be purified and separated, the pure product can be obtained only through simple suction filtration and separation after the reaction is finished, and the synthetic method is efficient and universal, is suitable for preparing a series of benzimidazolone, benzoxazolone and benzothiazolone compounds and has high industrial application value.

Selenium-Catalyzed Carbonylative Synthesis of 2-Benzimidazolones from 2-Nitroanilines with TFBen as the CO Source

A selenium-catalyzed carbonylative reaction for the synthesis of 2-benzimidazolones from 2-nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene-1,3,5-triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2-benzimidazolones were produced in moderate to excellent yields.

Method for synthesizing benzothiazolone-based and 1,3-disubstituted urea-based derivatives through activation of CO2

The present invention relates to a method for synthesizing benzothiazolone-based and 1,3-disubstituted urea-based derivatives through activation of CO2. According to the present invention, an inexpensive and easily-available sulfur-containing metal salt compound is first used as an activation catalyst for CO2, and a reaction raw material and CO2 are converted into a corresponding target compound at a low reaction temperature under a low CO2 pressure; and the method has high atomic economy, can reduce the generation of by-products, meets the standards of environmental friendliness and environmentally friendly chemistry, and is the effective way capable of completely utilizing CO2 as the renewable resource, developing new energy and achieving the beneficial cycle of carbon in nature.

Sulfated polyborate-catalyzed efficient and expeditious synthesis of (un)symmetrical ureas and benzimidazolones

The excellent catalytic potential of sulfated polyborate is utilized in the synthesis of (un)symmetrical ureas and benzimidazolones by heating amines or substituted OPDA and urea or N-phenylureas under a solvent-free condition at 120 °C is described. The key advantages of the present protocol are phosgene-free, and other hazardous reagents or organic solvent free, high reaction rates and yields, simple workup procedure, and recyclability of the catalyst.

Discovery of a Selective Aurora A Kinase Inhibitor by Virtual Screening

Here we report the discovery of a selective inhibitor of Aurora A, a key regulator of cell division and potential anticancer target. We used the atom category extended ligand overlap score (xLOS), a 3D ligand-based virtual screening method recently developed in our group, to select 437 shape and pharmacophore analogs of reference kinase inhibitors. Biochemical screening uncovered two inhibitor series with scaffolds unprecedented among kinase inhibitors. One of them was successfully optimized by structure-based design to a potent Aurora A inhibitor (IC50 = 2 nM) with very high kinome selectivity for Aurora kinases. This inhibitor locks Aurora A in an inactive conformation and disrupts binding to its activator protein TPX2, which impairs Aurora A localization at the mitotic spindle and induces cell division defects. This phenotype can be rescued by inhibitor-resistant Aurora A mutants. The inhibitor furthermore does not induce Aurora B specific effects in cells.

NOVEL BENZIMIDAZOLE DERIVATIVE AND USE THEREOF

The present invention aims to provide a compound capable of inhibiting PCA-1 that can be a target for a novel treatment method of various diseases, and pharmaceutical use of the compound. A compound represented by the formula (I): wherein each symbol is a

Design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors as anti-prostate cancer drugs

A series of 1-aryl-3,4-substituted-1H-pyrazol-5-ol derivatives was synthesized and evaluated as prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors to obtain a novel anti-prostate cancer drug. After modifying 1-(1H-benzimidazol-2-yl)-3,4-dimethyl-1H-pyrazol-5-ol (1), a hit compound found during random screening using a recombinant PCA-1/ALKBH3, 1-(1H-5- methylbenzimidazol-2-yl)-4-benzyl-3-methyl-1H-pyrazol-5-ol (35, HUHS015), was obtained as a potent PCA-1/ALKBH3 inhibitor both in vitro and in vivo. The bioavailability (BA) of 35 was 7.2% in rats after oral administration. As expected, continuously administering 35 significantly suppressed the growth of DU145 cells, which are human hormone-independent prostate cancer cells, in a mouse xenograft model without untoward effects.

A bifunctional tungstate catalyst for chemical fixation of CO2 at atmospheric pressure

No pressure: A simple monomeric tungstate, [WO4]2-, serves as a highly efficient homogeneous catalyst for various transformations of CO2 at atmospheric pressure. The tungsten-oxo moiety activates CO2 and the substrate simultaneously. The catalyst system is high yielding and applicable to a wide range of substrates such as amines (see scheme), 2-aminobenzonitriles, and propargylic alcohols. Copyright

Selenium-catalyzed reductive carbonylation of 2-nitrophenols to 2-benzoxazolones

2-Benzoxazolones or 2-benzimidazolones are synthesized in moderate to good yields in the presence of a base (KOH, NaOH, KOAc, NEt3, DBU) at atmospheric pressure or under a high pressure of CO by one-pot reductive carbonylation of 2-nitrophenols or 2-nitroaniline in the presence of selenium as catalyst. Besides the effect of base, the effects of solvent and temperature on the reaction were investigated at high or atmospheric pressure. Contrasting results were obtained for 2-benzoxazolones or 2-benzimidazolone at high and atmospheric pressures. Moreover, phase-transfer catalysis was exhibited. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Benzimidazole derivatives, preparation and therapeutic use thereof

The invention relates to benzimidazole derivatives of general formula (I) in which X represents a nitrogen atom or a carbon atom; and when X represents a nitrogen atom R3 represents in particular a hydrogen atom or a (C1-C4)alkyl group, R4 represents in p