2849-93-6

Basic information

• Product Name: 2-Benzimidazolecarboxylic acid
• Synonyms: Benzimidazole-2-carboxylic acid monohydrate;2-Benzimidazolecarboxylic acid;1H-benzo[d]imidazole-2-carboxylicacidhydrochloride;1H-benzimidazole-2-carboxylic acid(SALTDATA: 2H2O);2-CarboxybenziMidazole;1H-1,3-benzodiazole-2-carboxylic acid;2-Carboxy-1H-benzimidazole;1H-BENOXIMIDAZOLE-2-CARBOXYLIC ACID
• CAS NO: 2849-93-6
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.15
• Product Categories: Carboxylic Acids;Imidazoles & Benzimidazoles;BENZIMIDAZOLE;Benzimidazole Series;Heterocycles series;Imidazol&Benzimidazole
• Mol File: 2849-93-6.mol

Chemical Properties

• Melting Point: 169℃
• Boiling Point: 443.991 °C at 760 mmHg
• Flash Point: 222.318 °C
• Appearance: /
• Density: 1.507 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.743
• Storage Temp.: 2-8°C
• PKA: 1.44±0.30(Predicted)
• CAS DataBase Reference: 2-Benzimidazolecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Benzimidazolecarboxylic acid(2849-93-6)
• EPA Substance Registry System: 2-Benzimidazolecarboxylic acid(2849-93-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36/37/39-39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2849-93-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Benzimidazolecarboxylic acid is used as a key intermediate in the synthesis of novel drugs for various therapeutic applications. Its unique structure enables it to target specific biological pathways, making it a valuable component in the development of new medications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Benzimidazolecarboxylic acid serves as a building block for the creation of new pesticides and other agricultural chemicals. Its ability to interact with biological systems makes it a promising candidate for enhancing crop protection and yield.
Used in Dye and Pigment Production:
2-Benzimidazolecarboxylic acid is utilized in the production of dyes and pigments due to its chemical properties that contribute to color intensity and stability. This application is particularly relevant in industries such as textiles, plastics, and printing.
Used as a Reagent in Organic Chemistry:
As a reagent, 2-Benzimidazolecarboxylic acid plays a crucial role in various organic chemistry reactions. Its versatility in chemical processes makes it an essential tool for researchers and chemists in the development of new compounds and materials.

InChI:InChI=1/C8H6N2O2/c11-8(12)7-9-5-3-1-2-4-6(5)10-7/h1-4H,(H,9,10)(H,11,12)

Upstream product

• 3314-30-5 1H-benzoimidazole-2-carboxaldehyde 
• 4856-97-7 2-(Hydroxymethyl)benzimidazole 
• 16414-04-3 1-benzimidazol-2-ylethanol 
• 58758-09-1 (E)-2-styryl-1H-benzo[d]imidazole 
• 245-47-6 benzo[4,5]imidazo[1,2-a]pyridine 
• 67-56-1 methanol 
• 3878-19-1 fuberidazole 
• 5436-00-0 benzimidazole-2-carboxylic acid hydrazide 
• 107997-49-9 Benzimidazol-2-carbonsaeureazid 
• 3584-65-4 2-trichloromethyl-1H-benzoimidazole 
• 67162-12-3 2-(α-methylstyryl)benzimidazole 
• 939-70-8 2-acetylbenzimidazole 
• 74527-55-2 N-butyl-1H-benzo[d]imidazole-2-carboxamide 
• 910026-59-4 N-(2-amino-phenyl)-N'-butyl-oxalamide 

Downstream Products

• 18773-95-0 1-acetylbenzimidazole 
• 51-17-2 benzoimidazole 
• 5805-52-7 1H-benzo[d]imidazole-2-carboxamide 
• 14483-72-8 6H,13H-dibenzimidazo<1,2-a;1',2'-d>pyrazine-6,13-dione 
• 78903-06-7 1-(3,3,3-trifluoro-1-trifluoromethylpropenyl)benzimidazole 
• 2849-92-5 methyl 1-methyl-1H-benzo[d]imidazole-2-carboxylate 
• 6965-02-2 2,2'-bi-1H-benzimidazole 
• 134362-79-1 Ro 0437626 
• 73903-18-1 5-nitro-1⁽³⁾H-benzoimidazole-2-carboxylic acid 
• 910026-71-0 [6-amino-1H-benzimidazol-2-yl]-(4-benzyl-piperidin-1-yl)-methanone 
• 910026-73-2 (6-nitro-1H-benzimidazol-2-yl)-(4-benzyl-piperidin-1-yl)-methanone 

Relevant articles and documents

Structure-based design of novel benzimidazole derivatives as PIN1 inhibitors

Peptidyl-prolyl cis/trans isomerase Pin1 plays a key role in amplifying and translating multiple oncogenic signaling pathways during oncogenesis. The blockade of Pin1 provided a unique way of disrupting multiple oncogenic pathways and inducing apoptosis. Aiming to develop potent Pin1 inhibitors, a series of benzimidazole derivatives were designed and synthesized. Among the derivatives, compounds 6h and 13g showed the most potent Pin1 inhibitory activity with IC50 values of 0.64 and 0.37 μM, respectively. In vitro antiproliferative assay demonstrated that compounds 6d, 6g, 6h, 6n, 6o and 7c exhibited moderate antiproliferative activity against human prostate cancer PC-3 cells. Taken together, these unique benzimidazole derivatives exhibited great potential to be further explored as potent Pin1 inhibitors with improved potency.

Environmental Effects on the Absorption and Fluorescence Spectral Characteristics of Benzimidazole-2-carboxylic Acid and Its Esters

The absorption and fluorescence spectra of benzimidazole-2-carboxylic acid (BIA) and 5-chlorobenzimidazole-2-carboxylic acid (CBIA) have clearly indicated that benzimidazole (BI) ring and -COOH group are coplanar to each other and are held together in a rigid frame by intramolecular hydrogen-bonding.Dual fluorescence is observed in polar and hydrogen bonding solvents.The short wavelength fluorescence band is assigned to a structure where the -COOH group is perpendicular to the BI moiety and the long wavelength fluorescence band to the planar configuration.This is further manifested from the spectral characteristics of the ester of 5-chlorobenzimidazole-2-carboxylic acid (CBIM).Various prototropic reactions taking place in S0 ans S1 states for all the three molecules are studied in the H0/pH/H- range of -10 to 16.All the dissociation constants are determined, both in the S0 and S1 states and are discussed.

Green synthesis of 1,1-Carbonyldiimidazole using copper oxide nanofiber as a heterogeneous catalyst

Poly(vinyl pyrrolidone) (PVP)/copper oxide composite nanofibers were prepared by electrospinning technique using PVP and copper acetate as precursors and calcinated at high temperature to yield polymer free, phase pure copper oxide nanofibers (CuO NFs). T

Fragment-Based Optimization of Dihydropyrazino-Benzimidazolones as Metabotropic Glutamate Receptor-2 Positive Allosteric Modulators against Migraine

Our previous scaffold-hopping attempts resulted in dihydropyrazino-benzimidazoles as metabotropic glutamate receptor-2 (mGluR2) positive allosteric modulators (PAMs) with suboptimal drug-like profiles. Here, we report an alternative fragment-based optimization strategy applied on the new dihydropyrazino-benzimidazolone scaffold. Analyzing published high-affinity mGluR2 PAMs, we used a pharmacophore-guided approach to identify suitable growing vectors and optimize the scaffold in these directions. This strategy resulted in a new fragment like lead (34) with improved druglike properties that were translated to sufficient pharmacokinetics and validated proof-of-concept studies in migraine. Gratifyingly, compound34showed reasonable activity in the partial infraorbital nerve ligation, a migraine disease model that might open this indication for mGluR2 PAMs.

Discovery of heterocyclic carbohydrazide derivatives as novel selective fatty acid amide hydrolase inhibitors: design, synthesis and anti-neuroinflammatory evaluation

Fatty acid amide hydrolase (FAAH) is a promising target for the development of drugs to treat pain, inflammation, and other central nervous system disorders. Herein, a series of novel heterocyclic carbohydrazide derivatives were firstly designed by the classic scaffold-hopping strategy. Then, multi-steps synthesis and human FAAH enzyme inhibiting activity assays were conducted. Among them, compound 26 showed strong inhibition against human FAAH with IC50 of 2.8 μM. Corresponding docking studies revealed that the acyl hydrazide group of compound 26 well-occupied the acyl-chain binding pocket. It also exhibited high selectivity towards FAAH when comparing with CES2 and MAGL. Additionally, compound 26 effectively suppressed the LPS-induced neuroinflammation of microglial cells (BV2) via the reduction of interleukin-1β and tumor necrosis factor-α. Our results provided significative lead compounds for the further discovery of novel selective and safe FAAH inhibitors with potent anti-neuroinflammation activity.

Substituted heterocyclic compound containing urea skeleton and preparation method and application of substituted heterocyclic compound

The invention discloses a substituted heterocyclic compound containing a urea skeleton and a preparation method and application of the substituted heterocyclic compound, and relates to the field of pharmaceutical chemistry, in particular to the substituted heterocyclic compound containing the urea skeleton or pharmaceutically acceptable salt of the substituted heterocyclic compound, a pharmaceutical composition containing the compounds and medical application of the compounds. Particularly, the invention relates to application of the substituted heterocyclic compound as an FAAH inhibitor in preparing drugs for preventing or treating diseases associated with FAAH, such as depression, analgesia, cannabinoid using disorders and other related diseases.

Substituted heterocyclic compound containing acylhydrazone skeleton as well as preparation method and application thereof (by machine translation)

The invention discloses a substituted heterocyclic compound containing an acylhydrazone skeleton as well as a preparation method and application, of the substituted heterocyclic compound. The invention relates to the field, in particular to a substituted heterocyclic compound containing an acylhydrazone skeleton or a pharmaceutically acceptable salt, a pharmaceutical composition containing the compounds and medical application, in particular to an FAAH inhibitor, and application, in preparation of drugs for preventing or treating diseases related to FAAH, including depression, analgesia, cannabinoid use disorders and other related diseases. (by machine translation)

benzimidazole chiral heterocyclic compound as well as preparation method and application thereof

The invention discloses a benzimidazole chiral heterocyclic compound as well as a preparation method and application thereof. The structure formula of the benzimidazole chiral heterocyclic compound isshown in formula I, formula II or formula III in the description. The benzimidazole chiral heterocyclic compound is prepared by treating an iridium complex which is prepared through a metal iridium compound and a phosphoramidite ligand as a catalyst, performing intra-molecular allyl amination on allyl substrate, and then synthesizing with high efficiency and high enantioselectivity. The method has the advantages of being high in catalytic reaction activity, mild in reaction conditions, high in enantioselectivity, wide in substrate applicable scope, and environmentally friendly; the primary in-vitro enzyme inhibition activity test shows that the compound is high in alpha-glucosidase inhibiting activity and can be used as an alpha-glucosidase inhibiting agent, and the compound can also be used as a further modified drug intermediate; the compound has a potential application value in preventing or treating II-diabetes, obesity and complication medicines thereof and pilot compounds thereof.

1,2-dis-substituted benzimidazole derivative and application thereof

The invention belongs to the technical field of medicines, and particularly relates to a 1,2-dis-substituted benzimidazole derivative and pharmaceutically acceptable salt thereof, a preparation method of the derivative, a medicine composition with the derivative serving as an active component, and application of the derivative in preparation of a Pin1 inhibitor and preparation of a medicine for treating and/or preventing various cancers. The 1,2-dis-substituted benzimidazole derivative and the pharmaceutically acceptable salt thereof are as shown in the general formula I, and definitions of all substituents are described in claims and the specification. (Refer to Specification).

18 beta-glycyrrhetinic acid derivative and application thereof

The invention relates to the technical field of medicines, in particular to an 18 beta-glycyrrhetinic acid derivative with Pin1 inhibitory activity and pharmacologically-acceptable salt thereof, a preparation method of the derivative, a pharmaceutical composition taking the derivative as an active ingredient and application of the derivative to the preparation of a Pin1 inhibitor and the preparation of a drug for treating and/or preventing various cancers. The derivative shown in a general formula I or the pharmacologically-acceptable salt thereof has the following structure, wherein R, X, Y and n are stated in the claims and the descriptions.