87941-55-7

Basic information

• Product Name: 4-BROMO-1-TRITYL-1H-IMIDAZOLE
• Synonyms: 4-BROMO-1-TRITYL-1H-IMIDAZOLE;4-BROMO-1-TRITYLIMIDAZOLE;4-Bromo-1-trityl-1H-imidazde;4-Bromo-1-[tris(phenyl)methyl]-1H-imidazole;1-Trityl-4-BroMo IMidazole;4-Bromo-1-(triphenylmethyl)-1H-imidazole
• CAS NO: 87941-55-7
• Molecular Formula: C₂₂H₁₇BrN₂
• Molecular Weight: 389.29
• Product Categories: blocks;Bromides;Imidazoles;API intermediates
• Mol File: 87941-55-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 248-250 °C(Solv: ethanol (64-17-5))
• Boiling Point: 492.5 °C at 760 mmHg
• Flash Point: 251.7 °C
• Appearance: /
• Density: 1.27 g/cm³
• Vapor Pressure: 2.31E-09mmHg at 25°C
• Refractive Index: 1.629
• PKA: 3.60±0.61(Predicted)
• CAS DataBase Reference: 4-BROMO-1-TRITYL-1H-IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-1-TRITYL-1H-IMIDAZOLE(87941-55-7)
• EPA Substance Registry System: 4-BROMO-1-TRITYL-1H-IMIDAZOLE(87941-55-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 87941-55-7(Hazardous Substances Data)

Usage

General Description

4-Bromo-1-trityl-1H-imidazole is a chemical compound with the molecular formula C22H19BrN2. It is a derivative of imidazole, an aromatic heterocyclic compound, and features a trityl group (CPh3) and a bromine substituent. 4-Bromo-1-trityl-1H-imidazole is used in organic synthesis as a building block for the preparation of various pharmaceuticals and functional materials. It is also employed in the production of imidazoles, which are important in the field of medicinal chemistry as they exhibit various biological activities. Additionally, 4-Bromo-1-trityl-1H-imidazole may have other industrial and research applications due to its unique structure and reactivity.

InChI:InChI=1/C22H17BrN2/c23-21-16-25(17-24-21)22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-17H

Upstream product

• 2302-25-2 4-bromo-1 H-imidazole 
• 76-83-5 trityl chloride 
• 15469-97-3 N-tritylimidazole 

Downstream Products

• 1311569-36-4 1-oxo-N-[3-(1-trityl-1H-imidazol-4-yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxamide 
• 1311569-38-6 6-oxo-N-[3-(1-trityl-1H-imidazol-4-yl)phenyl]-7,8,9,10-tetrahydro-6H-pyrido[3',2':4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxamide 
• 1402838-08-7 2-[1-(triphenylmethyl)-1H-imidazol-4-yl]benzaldehyde 
• 197913-15-8 4-amino-1-triphenylmethylimidazole 
• 1033822-94-4 N-(1-trityl-1H-imidazol-4-yl)benzamide 
• 1380248-42-9 N-(1-trityl-1H-imidazol-4-yl)nicotinamide 
• 1311369-80-8 1-oxo-N-[3-(1-trityl-1H-imidazol-4-yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide 
• 725233-19-2 3-(1-trityl-1H-imidazol-4-yl)phenylamine 
• 121816-83-9 4-bromo-2-methyl-1-tritylimidazole 
• 23593-68-2 2-methyl-1-tritylimidazole 
• 76-84-6 triphenylmethyl alcohol 

Relevant articles and documents

INHIBITORS OF NOTCH SIGNALLING PATHWAY AND USE THEREOF IN TREATMENT OF CANCERS

The present invention relates to new inhibitors of Notch signalling pathway and its use in the treatment and/or prevention of cancers.

Synthesis, Biological Evaluation, and Molecular Modeling of 1 -Benzyl-1H-imidazoles as Selective Inhibitors of Aldosterone Synthase (CYP11B2)

Reducing aldosterone action is beneficial in various major diseases such as heart failure. Currently, this is achieved, with mineralocorticoid, receptor antagonists, however, aldosterone synthase (CYP 11B2) inhibitors may offer a promising alternative. In this study, we used three-dimensional modeling of CYP11B2 to model, the binding modes of the natural substrate 18-hydroxycorticosterone and the recently published CYP11B2 inhibitor R-fadrozole as a rational guide to design 44 structurally simple and achiral 1-benzyl-1H-imidazoles. Their syntheses, in vitro inhibitor potencies, and in silico docking are described. Some promising CYP11B2 inhibitors were identified, with our novel lead, MOERAS 115 (4-((5-phenyl-1H-imidazol-1-yl)methyl) benzonitrile) displaying an IC50 for CYP11B2 of 1.7 nM, and a CYP11B2 (versus CYP11B1) selectivity of 16.5, comparable to R-fadrozole (IC 50 for CYP11B26.0 nM, selectivity 19.8). Molecular docking of the inhibitors in the models enabled us to generate posthoc hypotheses on their binding modes, providing a valuable basis for future studies and further design of CYP11B2 inhibitors.

Synthesis and Reactions of Brominated 2-Nitroimidazoles

Various approaches to the synthesis of the hitherto-unknown 4(5)-bromo-2-nitroimidazole (5) are reported.Direct bromination of 2-nitroimidazole with N-bromosuccinimide gave the unreported 4,5-dibromo-2-nitroimidazole (10) in quantitative yield, but this could be selectively debrominated to give compound (5).While 1-methyl-2-nitroimidazole readily gave 4-bromo-1-methyl-2-nitroimidazole (15) on bromination, this could not be demethylated to give (5), and bromination of various other N-protected 2-nitroimidazoles was also unsuccessful.Lithiation of 4-bromo-1-tritylimidazole (21) followed by quenching with propyl nitrate gave (after detritylation and methylation) a mixture of a dimer (28) and compound (15), indicating that the desired product (5) is produced in this reaction although it can only be isolated in derivatized form.The proposed route for formation of the dimer suggests a general reaction between 1-alkyl-4-bromo-2-nitroimidazoles and strong C- and N-nucleophiles, resulting in substitution at the 5-position.