573-33-1

Basic information

• Product Name: 2,4,5-triphenyl-2-imidazoline
• Synonyms: 2,4,5-triphenyl-2-imidazoline;(4R)-2,4α,5α-Triphenyl-2-imidazoline;(4S,5R)-2,4,5-Triphenyl-2-imidazoline;(4α,5α)-4,5-Dihydro-2,4,5-triphenyl-1H-imidazole
• CAS NO: 573-33-1
• Molecular Formula: C₂₁H₁₈N₂
• Molecular Weight: 298.38102
• EINECS: 209-354-2
• Mol File: 573-33-1.mol
• Article Data: 16

Chemical Properties

• Melting Point: 134.5°C
• Boiling Point: 429.8°C (rough estimate)
• Flash Point: 226.5°C
• Appearance: /
• Density: 1.0750 (rough estimate)
• Vapor Pressure: 2.53E-08mmHg at 25°C
• Refractive Index: 1.8000 (estimate)
• PKA: 8.66±0.70(Predicted)
• CAS DataBase Reference: 2,4,5-triphenyl-2-imidazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,5-triphenyl-2-imidazoline(573-33-1)
• EPA Substance Registry System: 2,4,5-triphenyl-2-imidazoline(573-33-1)

Safety Data

• Hazardous Substances Data: 573-33-1(Hazardous Substances Data)

Usage

General Description

2,4,5-triphenyl-2-imidazoline is a chemical compound that belongs to the imidazoline class of chemicals. It is a white to off-white crystalline solid that is insoluble in water and most organic solvents. It is primarily used as an intermediate in the synthesis of other chemicals, such as dyes, pharmaceuticals, and agrochemicals. It has also been studied for its potential use in corrosion inhibition and as a reagent in organic synthesis. Additionally, 2,4,5-triphenyl-2-imidazoline has been investigated for its potential biological activity, including its possible role as an antagonist of alpha-adrenergic receptors. Further research is needed to fully understand the applications and properties of this chemical compound.

InChI:InChI=1/C21H18N2/c1-4-10-16(11-5-1)19-20(17-12-6-2-7-13-17)23-21(22-19)18-14-8-3-9-15-18/h1-15,19-20H,(H,22,23)

Upstream product

• 538-51-2 benzylidene phenylamine 
• 92-29-5 hydrobenzamide 
• 64-17-5 ethanol 
• 7664-41-7 ammonia 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 100-52-7 benzaldehyde 
• 951-87-1 meso-1,2-diphenyl-1,2-diaminoethane 
• 825-60-5 benzimidic acid ethyl ester 
• 92-29-5 (E,E)-1,3,5-triphenyl-2,4-diazapenta-1,4-diene 
• 65-85-0 benzoic acid 
• 16118-22-2 benzylidenamine 
• 57-13-6 urea 
• 54874-97-4 N-(erythro-α'-amino-bibenzyl-α-yl)-benzamide 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 87671-32-7 N,N'-((1R,2R)-1,2-diphenylethane-1,2-diyl)dibenzamide 
• 484-47-9 lophine 
• 3190-01-0 racem-N,N'-dibenzylidene-bibenzyl-α,α'-diyldiamine 
• 65-85-0 benzoic acid 
• 3190-22-5 erythro-N-benzoyl-N'-phenylmethylidene-1,2-diamino-1,2-diphenylethane 
• 881662-21-1 1,3-diallyl amarine bromide 
• 951-87-1 rac-1,2-diphenylethylene-1,2-diamine 
• 80424-18-6 (4R,5R)-2,4,5-Triphenyl-imidazolidine 
• 493-77-6 2,4,6-triphenyl-1,3,5-triazine 
• 642-04-6 2,3,5,6-tetraphenylpyrazine 
• 33722-46-2 isoamarine 
• 33722-47-3 DL-(4R,5S)-1-benzyl-2,4,5-triphenyl-4,5-dihydro-1H-imidazole 
• 216861-21-1 (1S,2S)-N,N'-(1,2-diphenylethane-1,2-diyl)diacetamide 
• 91840-93-6 (1S,2S)-N,N'-diethyl-1,2-diphenyl-1,2-ethanediamine 

Relevant articles and documents

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Nuclear factor-κB mediated inhibition of cytokine production by imidazoline scaffolds

The mammalian nuclear transcription factor NF-κB is responsible for the transcription of multiple cytokines, including the pro-inflammatory cytokines tumor necrosis factor alpha (TNF-α) and interleukin 6 (IL-6). Elevated levels of pro-inflammatory cytokines play an important role in the pathogenesis of inflammatory disorders such as rheumatoid arthritis (RA). Inhibition of the pro-inflammatory transcription factor NF-κB has therefore been identified as a possible therapeutic treatment for RA. We describe herein the synthesis and biological activity of a series of imidazoline-based scaffolds as potent inhibitors of NF-κB mediated gene transcription in cell culture as well as inhibitors of TNF-α and IL-6 production in interleukin 1 beta (IL-1β) stimulated human blood.

On the racemization of chiral imidazolines

(Chemical Equation Presented) Racemization of chiral imidazolines with base has been studied for the first time following an unexpected finding in the synthesis of chiral imidazoline ligands. Amine bases do not cause racemization. Strong inorganic bases can induce racemization, yet this occurs only when the nitrogen is unsubstituted, in agreement with a symmetry-allowed thermal disrotatory ring opening and closure from a diazapentadienyl anion. Surprisingly, even with electron-withdrawing N-substituents, no racemization is observed. Conditions which allow for the racemization-free manipulations of this important compound class have been defined and developed.