22927-61-3

Usage

Uses

Used in Flame Retardant Industry:
2,4,5-TRIBROMO-1-(METHOXYMETHYL)-1H-IMIDAZOLE is used as a flame retardant for enhancing the fire resistance of materials. The bromine atoms in its structure contribute to its flame retardant properties by interrupting the combustion process and reducing the flammability of materials.
Used in Polymer and Plastics Industry:
2,4,5-TRIBROMO-1-(METHOXYMETHYL)-1H-IMIDAZOLE is used in the production of polymers and plastics to improve their thermal stability and flame resistance. Its incorporation into polymer matrices can enhance the overall performance and safety of the final products.
Used in Pharmaceutical Industry (Potential):
2,4,5-TRIBROMO-1-(METHOXYMETHYL)-1H-IMIDAZOLE may have potential applications in the pharmaceutical industry, although further research is needed to determine its specific properties and potential uses. Its unique structure and functional groups could potentially be exploited for the development of new drugs or drug delivery systems.
Used in Environmental and Health Research:
Due to the presence of bromine in 2,4,5-TRIBROMO-1-(METHOXYMETHYL)-1H-IMIDAZOLE, it may be the subject of research in the field of environmental and health sciences. Studies could focus on understanding its environmental impact, potential toxicity, and safe handling and disposal methods to ensure its responsible use in various applications.

Upstream product

• 2034-22-2 2,4,5-tribromo-1H-imidazole 
• 107-30-2 chloromethyl methyl ether 
• 13057-17-5 bromethyl methyl ether 

Downstream Products

• 101853-84-3 4,5-dibromo-1-methoxymethyl-2-phenylthioimidazole 
• 101853-83-2 2-benzylthio-4,5-dibromo-1-methoxymethylimidazole 
• 159589-94-3 4,5-dibromo-1-methoxymethyl-2-phenyl-1H-imidazole 
• 2034-22-2 2,4,5-tribromo-1H-imidazole 
• 1251931-20-0 4-(4,5-dibromo-1-methoxymethyl-1H-imidazol-2-yl)phenol 
• 1251931-21-1 {2-[4-(4,5-dibromo-1-methoxymethyl-1H-imidazol-2-yl)phenoxy]ethyl}dimethylamine 
• 101853-97-8 ethyl 2-benzylthio-1-methoxymethyl-1H-thieno<2,3-d>imidazole-5-carboxylate 
• 101853-90-1 2-benzylthio-4-bromo-1-methoxymethylimidazole-5-carbaldehyde 
• 101853-91-2 4-bromo-1-methoxymethyl-2-phenylthioimidazole-5-carbaldehyde 
• 159590-03-1 4-bromo-1-methoxymethyl-2-phenyl-1H-imidazole 

Relevant academic research and scientific papers

ANTI-INFECTIVE COMPOUNDS

The present invention relates to small molecule compounds having the general formula (I): wherein A is a moiety selected from the group consisting of formulae (A) to (K) and their use in the treatment of bacterial infections, in particular Tuberculosis.

Potent BRAF kinase inhibitors based on 2,4,5-trisubstituted imidazole with naphthyl and benzothiophene 4-substituents

The RAS-RAF-MEK-ERK pathway is hyperactivated in 30% of human cancers. BRAF is a serine-threonine kinase, belonging to this pathway that is mutated with high frequency in human melanoma and other cancers thus BRAF is an important therapeutic target in melanoma. We have designed inhibitors of BRAF based on 2,4,5-trisubstituted imidazoles with naphthyl and benzothiophene-4-substituents. Two compounds were discovered to be potent BRAF inhibitors: 1-(6-{2-[4-(2-dimethylamino-ethoxy)phenyl]-5-(pyridin-4-yl)-1H-imidazol-4-yl} benzo[b]thiophen-3-yl)-2,2,2-trifluoroethanol (1i) with BRAF IC50 = 190 nM and with cellular GI50 = 2100 nM, and 6-{2-[4-(2- dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-naphthalen-1-ol (1q) with IC50 = 9 nM and GI50 = 220 nM.

Novel tricyclic pyrazole BRAF inhibitors with imidazole or furan central scaffolds

V-RAF murine sarcoma viral oncogene homolog B1 (BRAF) is a serine/threonine-specific protein kinase that is mutated with high frequency in cutaneous melanoma, and many other cancers. Inhibition of mutant BRAF is an attractive therapeutic approach for the treatment of melanoma. A triarylimidazole BRAF inhibitor bearing a phenylpyrazole group (dimethyl-[2-(4-{5-[4-(1H-pyrazol-3-yl)-phenyl]-4-pyridin-4-yl-1H-imidazol-2-yl} -phenoxy)-ethyl]-amine, 1a) was identified as an active BRAF inhibitor. Based on this starting point, we synthesized a series of analogues leading to the discovery of 6-{2-[4-(4-methyl-piperazin-1-yl)-phenyl]-5-pyridin-4-yl-3H- imidazol-4-yl}-2,4-dihydro-indeno[1,2-c]pyrazole (1j), with nanomolar activity in three assays: inhibition of purified mutant BRAF activity in vitro; inhibition of oncogenic BRAF-driven extracellular regulated kinase (ERK) activation in BRAF mutant melanoma cell lines; and inhibition of proliferation in these cells.

Azoles. Part 4. Nucleophilic Substitution Reactions of Halogenoimidazoles

A number of N-protected derivatives of 2,4,5-tribromoimidazole, 4(5)-bromo-5(4)-nitroimidazole, and 2,4(5)-dibromo-5(4)-nitroimidazole have been prepared by standard procedures and treated with various nucleophiles.Whereas 2,4,5-tribromo (and tri-iodo)imidazole reacted with sodium benzenethiolate to give the corresponding 4,5-dihalogenoimidazole and diphenyl disulphide, 1-protected derivatives of 2,4,5-tribromoimidazole reacted with various sodium alkane (or arene)thiolates and with sodium isopropoxide, in isoprpopyl alcohol, by displacement of the 2-bromine atom. 1-Benzyl-5-bromo-4-nitroimidazole (14), 2-(5-bromo-4-nitroimidazol-1-yl)acetate (25), and 5-bromo-4-nitro-1-phenacylimidazole (26) reacted by displacement of the 5-bromine atom.The product arising from reaction of the last compound with ethyl 2-mercaptoacetate in ethanol in the presence of base, cyclised to give ethyl 3-hydroxy-7-nitro-3-phenylimidazolothiazine-2-carboxylate (35).

A Convenient Synthesis of Thienoimidazoles

1-Protected and 1,2-diprotected derivatives of 4-bromoimidazole-5-carbaldehyde were prepared from imidazole via 2,4,5-tribromoimidazole and reacted with ethyl 2-mercaptoethanoate to give the title compounds.