6868-37-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Benzimidazolcarbonitrile is used as a synthetic building block for the development of various pharmaceuticals. Its unique chemical structure allows for the creation of new compounds with potential therapeutic applications.
Used in Agrochemical Industry:
2-Benzimidazolcarbonitrile is used as an active ingredient in the formulation of crop protection products due to its fungicidal and insecticidal properties. It helps in safeguarding crops from pests and diseases, thereby ensuring increased agricultural productivity.
Used in Dye and Pigment Industry:
2-Benzimidazolcarbonitrile is used as an intermediate in the production of dyes and pigments. Its versatile chemical properties enable the synthesis of a wide range of colorants for various applications, including textiles, plastics, and printing inks.
Used in Specialty Chemicals Industry:
2-Benzimidazolcarbonitrile is employed as a precursor in the synthesis of specialty chemicals, such as advanced materials and fine chemicals. Its unique structure and reactivity contribute to the development of innovative products with specific properties and applications.

InChI:InChI=1/C8H5N3/c9-5-8-10-6-3-1-2-4-7(6)11-8/h1-4H,(H,10,11)

Upstream product

• 3584-65-4 2-trichloromethyl-1H-benzoimidazole 
• 3173-92-0 Benzimidazol-aldehyd-(2)-oxim 
• 88-74-4 2-nitro-aniline 
• 95-54-5 1,2-diamino-benzene 
• 75318-43-3 4,5-dichloro-1,2,3-dithiazolium chloride 
• 57097-49-1 2-cyano-benzimidazole-N-oxide 

Downstream Products

• 14483-74-0 benzimidazole-2-carboxamide oxime 
• 43102-21-2 2-(1H-tetrazol-5-yl)-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel scaffold benzo[4,5]imidazo [1,2-a]pyrazin-1-amine: Towards adenosine A2A receptor (A2A AR) antagonist

Antagonists of adenosine receptor are under exploration as potential drug candidates for treatment of neurological disorders, depression, certain cancers and potentially used as a cancer immunotherapy. Herein, we describe design and synthesis of novel scaffold benzo[4,5]imidazo [1,2-a]pyrazin-1-amine (6) derivatives. All the compounds were evaluated for A2A AR antagonist activity and displayed encouraging results (IC50 9–300 nM) of A2A AR antagonist binding affinity in biochemical assay. Compound 27 exhibits good activity in A2A AR antagonist cAMP functional assay (IC50 31 nM) and further this compound shows T-cell activation at the IL-2 production assay (EC50 165 nM). Molecular docking studies were carried out to rationalize the observed binding affinity of compound 27.

A convenient reagent for the conversion of aldoximes into nitriles and isonitriles

For the dehydroxylation of aldoximes with 4-nitro-1-((trifluoromethyl)sulfonyl)-imidazole (NTSI), slight modifications of reaction conditions resulted in significantly different reaction paths to provide either nitriles or isonitriles. The challenging conversion of aldoximes into isonitriles was achieved under mild conditions.

3-benzo[4,5]imidazo[1,2-a]pyrazin-1-amine compounds as well as preparation method and application thereof

The invention discloses 3-benzo[4,5]imidazo[1,2-a]pyrazin-1-amine compounds as well as a preparation method and application thereof. The general structure of the compounds is shown as a formula (I). The compounds disclosed by the invention have good inhibitory activity on an adenosine A2A receptor, and in particular, IC50 values of the compounds 1-3, compounds 7-11, compounds 13-15, and compounds18, 23, 25, 26, 29, 30 and 31 on the adenosine A2A receptor is 50 nM or below, and the IC50 values of the compounds 14, 23, 25, 30 and 31 is 10.1 nM or below. The disclosed compounds show excellent inhibitory effect on adenosine A2A receptors, can be prepared into adenosine A2A receptor inhibitors to serve as potential immune antitumor drugs, and release the scavenging function of an immune systemon tumor cells by inhibiting the activity of the adenosine A2A receptor, thereby achieving the effect of treating tumors. Meanwhile, the compounds are simple in synthesis method, mild in condition, high in product yield and purity, capable of being industrially produced and prepared on a large scale and convenient to apply and popularize.

Sequence-specific 2-cyanobenzothiazole ligation

The use of small, natural chemical reporters in conjunction with catalyst-free bioorthogonal reactions will greatly streamline protein labeling in a cellular environment with minimum perturbation to their function. Here we report the discovery of a 2-cyan

The synthesis of tetrazoles in nanometer aqueous micelles at room temperature

A newly developed nonionic amphiphile (GPGS-1500), a diester composed of a Guerbet alcohol (2-octyldodecan-1-ol), poly(ethylene glycol) 1500 (PEG 1500), and succinic acid esters, has been prepared as an effective nanomicelle-forming species for the synthesis of tetrazoles in water at room temperature. We have designed a new nonionic amphiphile (GPGS-1500) for the synthesis of tetrazoles in water at room temperature. The reaction conditions were optimized, and the size of the micelles formed by GPGS-1500 in water was measured by dynamic light scattering. Copyright

The Synthesis of Tetrazoles in Nanometer Aqueous Micelles at Room Temperature

A newly developed nonionic amphiphile (GPGS-1500), a diester composed of a Guerbet alcohol (2-octyldodecan-1-ol), poly(ethylene glycol) 1500 (PEG 1500), and succinic acid esters, has been prepared as an effective nanomicelle-forming species for the synthesis of tetrazoles in water at room temperature.

Synthesis of novel histamine H4 receptor antagonists

This letter describes the discovery and synthesis of a series of octahydropyrrolo[3,4-c]pyrrole based selective histamine hH4 receptor antagonists. The amidine compound 20 was found to be a potent and selective histamine H4 receptor antagonist with moderate clearance and a high volume of distribution.

MIF MODULATORS

The invention provides novel heterocyclic compounds, pharmaceutical compositions and methods of treatment that modulate levels of MIF expression and treat disorders associated with high or low levels of MIF expression

New route to 2-cyanobenzimidazoles

N-Monosubstituted 1,2-diaminobenzenes 4 (R = Me, Ph, PhCH2, and 3,4- Me2C6H3CH2) react with 4,5-dichloro-1,2,3-dithiazolium chloride 1 in dichloromethane at room temperature to give the corresponding 2- cyanobenzimidazoles 6. If pyridine is added at the beginning of the reaction, the intermediate imino-1,2,3-dithiazoles 5 can be isolated. Upon thermolysis, most of the imines 5 give the 2-cyanobenzimidazoles 6 in fair to good yields. 1.2-Diaminobenzene can be converted in high yield into the mono-imine 5i or the bis-imine 12, R = H; thermolysis of 5i gives 2-cyanobenzimidazole in high yield. Conversion of 5 into 6 involves the loss of both sulfur atoms and with the N-phenylimino derivative 5b singlet diatomic sulfur, S2, has been intercepted with norbornene and with 2.3-diphenylbutadiene to give the expected cycloadducts 7 and 8.

The Cycloaddition Reactions of Benzimidazole-2-carbonitrile Oxide with Alkenes

Benzimidazole-2-carbonitrile oxide was prepared in situ and reacted with vinyl acetate, acrylonitrile, styrene, phenyl vinyl sulfone and 3,3,3-trifluoropropene to afford 2-(5'-acetoxyisoxazolin-3'-yl)-, 2-(5'-cyanoisoxazolin-3'-yl)-, 2,-(5'-phenylisoxazol