1-[4-(4-bromophenyl)butyl]-1H-imidazole

Base Information

• Chemical Name: 1-[4-(4-bromophenyl)butyl]-1H-imidazole
• CAS No.: 1093058-52-6
• Molecular Formula: C₁₃H₁₅BrN₂
• Molecular Weight: 279.18

Synonyms:1-[4-(4-bromophenyl)butyl]-1H-imidazole

Chemical Property of 1-[4-(4-bromophenyl)butyl]-1H-imidazole

Chemical Property:

• Boiling Point: 435.0±28.0 °C(Predicted)
• Density: 1.31±0.1 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

HO-1-IN-1 99.91% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of 1-[4-(4-bromophenyl)butyl]-1H-imidazole

There total 7 articles about 1-[4-(4-bromophenyl)butyl]-1H-imidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 46.0%

4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanone (939825-22-6) → 1-[4-(4-bromophenyl)butyl]-1H-imidazole (1093058-52-6)

Guidance literature:

With potassium hydroxide; hydrazine; In ethylene glycol; at 100 - 195 ℃; for 12.5h;

Reference yield:

1-bromomethyl-4-bromobenzene (589-15-1) → 1-[4-(4-bromophenyl)butyl]-1H-imidazole (1093058-52-6)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / methanol / 16 h / Heating / reflux

2: bromine / methanol / 2 h / 20 °C

3: N,N-dimethyl-formamide / 1 h / 20 °C

4: potassium hydroxide; hydrazine / ethylene glycol / 12.5 h / 100 - 195 °C

With potassium hydroxide; bromine; potassium carbonate; hydrazine; In methanol; ethylene glycol; N,N-dimethyl-formamide;

Reference yield:

4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanol (940061-41-6) → 1-[4-(4-bromophenyl)butyl]-1H-imidazole (1093058-52-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: phosphorus pentoxide; dimethyl sulfoxide / 72.5 h / 0 - 20 °C

1.2: 0.17 h / 0 °C

2.1: potassium hydroxide; hydrazine / ethylene glycol / 12.5 h / 100 - 195 °C

With potassium hydroxide; phosphorus pentoxide; dimethyl sulfoxide; hydrazine; In ethylene glycol;

upstream raw materials:

4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanone

4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanol

1-bromo-4-(4-bromophenyl)-2-butanone

4-(4-bromo-phenyl)-1,2-epoxy-butane

Downstream raw materials:

1-[4-(4-bromophenyl)butyl]-1H-imidazole hydrochloride

Refernces

Benzylidenemalononitrile compounds as activators of cell resistance to oxidative stress and modulators of multiple signaling pathways. A structure-activity relationship study

10.1016/j.bcp.2011.05.028

The research, titled "Benzylidenemalononitrile compounds as activators of cell resistance to oxidative stress and modulators of multiple signaling pathways: A structure–activity relationship study," investigates the structure–activity relationship of benzylidenemalononitrile (BMN) compounds and their capacity to induce heme oxygenase-1 (HO-1) gene expression, activate upstream signaling pathways, and protect cells against oxidative stress. The study used U937 human monocytic cells and examined 49 BMNs and related compounds. Key findings include the discovery that electron-withdrawing groups (NO2, CN, halogens) and double meta MeO substituents in BMN molecules increase HO-1 gene induction, while electron-donating groups (OH, MeO, N-morpholino) significantly decrease it. The study also revealed that the activation of c-Jun, Nrf2, p38 MAPK, and p70S6K correlated with specific substitution patterns in the BMN structure. Furthermore, BMN-dependent maximal up-regulation of HO-1 required a parallel increase in Nrf2 and phospho-c-Jun cellular levels. The research concludes that BMNs induce the expression of protective genes by alkylating sensitive cysteine residues of regulatory factors, providing insights into their potential as therapeutic agents for conditions involving oxidative stress.

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