96797-15-8

Basic information

• Product Name: 4-Iodo-1-tritylimidazole
• Synonyms: 4-Iodo-1-[tris(phenyl)methyl]-1H-imidazole;1-(TriphenylMethyl)-4-iodoiMidazole;(4-Iodo-1H-imidazol-1-yl)triphenylmethane, 1,1',1"-[(4-Iodo-1H-imidazol-1-yl)methanetriyl]tribenzene;2-Bromo-5,6-dichloro-1H-benzoimidazole;N-trityl-4(5)-iodoimidazole;1H-IMIDAZOLE, 4-IODO-1-(TRIPHENYLMETHYL)-;1-TRITYL-4-IODOIMIDAZOLE;AKOS 6
• CAS NO: 96797-15-8
• Molecular Formula: C₂₂H₁₇IN₂
• Molecular Weight: 436.29
• Product Categories: blocks;Imidazoles;Iodides;Aromatics;Heterocycles;Miscellaneous Reagents
• Mol File: 96797-15-8.mol
• Article Data: 29

Chemical Properties

• Melting Point: 224 °C
• Boiling Point: 509.7 °C at 760 mmHg
• Flash Point: 262 °C
• Appearance: off-white solid.
• Density: 1.4 g/cm³
• Vapor Pressure: 5.3E-10mmHg at 25°C
• Refractive Index: 1.653
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Very Slightly)
• PKA: 3.80±0.61(Predicted)
• CAS DataBase Reference: 4-Iodo-1-tritylimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Iodo-1-tritylimidazole(96797-15-8)
• EPA Substance Registry System: 4-Iodo-1-tritylimidazole(96797-15-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 96797-15-8(Hazardous Substances Data)

Usage

Description

4-Iodo-1-tritylimidazole, with the chemical formula C20H16IN3 and CAS number 96797-15-8, is an organic compound characterized by the presence of an imidazole ring and an iodine atom. It is a versatile reagent in the field of organic synthesis, known for its unique properties and potential applications.

Uses

Used in Organic Synthesis:
4-Iodo-1-tritylimidazole is used as a reagent in organic synthesis for various purposes. Its iodine atom can act as a leaving group, facilitating reactions such as nucleophilic substitutions and cross-coupling reactions. This property makes it a valuable tool in the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 4-Iodo-1-tritylimidazole is employed as a building block for the development of new drugs and drug candidates. Its imidazole ring is a common structural motif found in many biologically active molecules, and its iodination can enhance the lipophilicity and metabolic stability of the resulting compounds.
Used in Material Science:
4-Iodo-1-tritylimidazole also finds applications in material science, particularly in the synthesis of functional materials with specific properties. For example, it can be used to create ionic liquids, which are salts with low melting points and unique solvation properties, or to develop new types of polymers with tailored characteristics.

InChI:InChI=1/C22H17IN2/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

• 71759-89-2 4-iodoimidazole 
• 76-83-5 trityl chloride 
• 60-29-7 diethyl ether 

Downstream Products

• 135773-29-4 5-Hydroxy-5-(1-trityl-1H-imidazol-4-yl)-pentanoic acid methyl ester 
• 151607-58-8 1,1-Bis(methylthio)-2-fluoro-3-((1'-trityl)-4'-imidazolyl)prop-1-en-3-ol 
• 135773-27-2 1-triphenylmethyl-4-[(1-hydroxy-1-phenyl)methyl]-1H-imidazole 
• 15469-97-3 N-tritylimidazole 
• 67478-50-6 1-(triphenylmethyl)-1H-imidazole-2-carboxaldehyde 
• 33016-47-6 (1-tritylimidazol-4-yl)carboxaldehyde 
• 96797-16-9 1-tritylimidazole-2,4-dicarboxaldehyde 
• 135773-30-7 Bis-(4-chloro-phenyl)-(1-trityl-1H-imidazol-4-yl)-methanol 
• 161530-05-8 4-<(1-hydroxy-1-phenyl-2,2,2-trifluoro)ethyl>-N-triphenylmethylimidazole 
• 185798-88-3 1-(pyridine-4-yl)-1-(1-trityl-1H-imidazol-5-yl)methanol 
• 196870-07-2 1-(1-Trityl-1H-imidazol-4-yl)-2,3-dihydro-1H-phenalen-1-ol 
• 178556-70-2 4-(1-Trityl-1H-imidazol-4-yl)-1,2,3,4-tetrahydro-phenanthren-4-ol 
• 156833-28-2 4-<(1-naphthyl)hydroxymethyl>-N-(triphenylmethyl)imidazole 
• 192987-46-5 4-[1-(1-hydroxy-4-methylindanyl)]-N-(triphenylmethyl)imidazole 

Relevant articles and documents

Preparation method of (2-(1H-imidazole-4-yl)phenyl)methanol

The invention belongs to the technical field of medicinal chemistry, and particularly discloses a preparation method of (2-(1H-imidazole-4-yl)phenyl)methanol. Amino of 4-iodine-1H-imidazole is protected by a triphenylmethyl protecting group and reacts wit

Design and synthesis of indoleamine 2,3-dioxygenase 1 inhibitors and evaluation of their use as anti-tumor agents

Indoleamine 2,3-dioxygenase (IDO) 1 is the key enzyme for regulating tryptophan metabolism and is an important target for interrupting tumor immune escape. In this study, we designed four series of compounds as potential IDO1 inhibitors by attaching various fragments or ligands to indole or phenylimidazole scaffolds to improve binding to IDO1. The compounds were synthesized and their inhibitory activities against IDO1 and tryptophan 2,3-dioxygenase were evaluated. The cytotoxicities of the compounds against two tumor cell lines were also determined. Two compounds with a phenylimidazole scaffold (DX-03-12 and DX-03-13) showed potent IDO1 inhibition with IC50 values of 0.3–0.5 μM. These two IDO1 inhibitors showed low cell cytotoxicity, which indicated that they may exert their anti-tumor effect via immune modulation. Compound DX-03-12 was investigated further by determining the in vivo pharmacokinetic profile and anti-tumor efficacy. The pharmacokinetic study revealed that DX-03-12 had satisfactory properties in mice, with rapid absorption, moderate plasma clearance (～36% of hepatic blood flow), acceptable half-life (～4.6 h), and high oral bioavailability (～96%). Daily oral administration of 60 mg/kg of compound DX-03-12 decreased tumor growth by 72.2% after 19 days in a mouse melanoma cell B16-F10 xenograft model compared with the untreated control. Moreover, there was no obvious weight loss in DX-03-12-treated mice. In conclusion, compound DX-03-12 is a potent lead compound for developing IDO1 inhibitors and anti-tumor agents.

Fused imidazole compounds with indoleamine 2,3-dioxygenase inhibition activity

The invention relates to fused imidazole compounds, and a preparation method and application thereof. The structure of the compounds is shown in a general formula I, wherein the definitions of each group are as described in the specification. The compounds are capable of selectively inhibiting indoleamine 2,3-dioxygenase (IDO). The compounds provided by the invention can be used as IDO inhibitorsfor the treatment and/or prevention of diseases with the pathological characteristics of IDO mediated tryptophan metabolism pathways, such as cancer, eye diseases, autoimmune diseases, psychological disorders, depression, anxiety and other diseases.