2851-13-0

Usage

Uses

Used in Organic Synthesis:
N,N-dimethyl-1H-benzoimidazol-2-amine is used as a building block in organic synthesis for the creation of various pharmaceuticals and bioactive compounds.
Used in Medicinal Chemistry:
N,N-dimethyl-1H-benzoimidazol-2-amine is used as a key component in medicinal chemistry for the development of new drugs and therapeutic agents.
Used in Biological Research:
N,N-dimethyl-1H-benzoimidazol-2-amine is used as a potent inhibitor of tyrosine kinases in biological research, which are important enzymes involved in cell signaling and cancer development. This makes it a valuable tool for studying the mechanisms of these enzymes and their role in disease processes.

InChI:InChI=1/C9H11N3/c1-12(2)9-10-7-5-3-4-6-8(7)11-9/h3-6H,1-2H3,(H,10,11)

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 

Relevant academic research and scientific papers

Chloroformamidinium salts: Efficient reagents for preparation of 2-aminobenzoimidazole, 2-aminobenzoxazole, and 2-aminobenzothiazole derivatives

A Reaction involving chloroformamidinium salts (TCFH 1a, BTCFH 1b, DmCFH 1c, DmPCFH 1d, BPCFH 1e) and 2-aminophenol 9a, benzene-1,2-diamine 9b, and 2-aminothiophenol 9c afforded 2-aminobenzoxazole 13, 2-aminobenzoimidazole 14, and 2-aminobenzothiazole 15 derivatives, respectively as major products, due to the in situ heterocyclization with dimethylamine acting as the better leaving group. Attempts for preparation of 13-15 from the reaction of N,N-dimethyl carbomyl chloride 16 with 2-aminophenol 9a, benzene-1,2-diamine 9b, and 2-aminothiophenol 9c were unsuccessful, and gave the unexpected products benzoxazol-2-ol 18a, benzoimidazol-2-one 18b, and S-(2-amino-phenyl) N,N-dimethylthiocarbamate 19 respectively. On the other hand reaction of chloroformamidinium salts 1a-e with 3-benzyl-2-hydrazinoquinoxaline 3 and 1-hydrazinophthalazine hydrochloride 4 in the presence of triethylamine as a base, afforded the [1,2,4]triazolo derivatives 6 and 7 respectively in good yield and purity. These triazole derivatives were formed due to the strong tendency towards heterocyclization and substitution of dimethylamine group as a better leaving group.