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

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

Uses

Used in Chemical Synthesis:
2,4,5-triphenyl-2-imidazoline is used as an intermediate in the synthesis of other chemicals for its ability to contribute to the formation of complex organic compounds. This includes its role in the production of dyes, pharmaceuticals, and agrochemicals, where its structural features are essential for the desired chemical reactions.
Used in Corrosion Inhibition:
2,4,5-triphenyl-2-imidazoline is studied for its potential use in corrosion inhibition, where it may serve as a protective agent against the degradation of materials, particularly in industrial applications where metal surfaces are exposed to corrosive environments.
Used in Organic Synthesis as a Reagent:
In the field of organic synthesis, 2,4,5-triphenyl-2-imidazoline is utilized as a reagent, facilitating specific chemical reactions that are crucial for the development of new organic compounds and materials.
Used in Biological Research:
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. This research is significant for understanding its interaction with biological systems and exploring its potential therapeutic applications.
Further research is necessary to fully explore the applications and properties of 2,4,5-triphenyl-2-imidazoline, expanding its use across various industries and scientific domains.

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

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

Downstream Products

• 33722-46-2 isoamarine 
• 33722-47-3 DL-(4R,5S)-1-benzyl-2,4,5-triphenyl-4,5-dihydro-1H-imidazole 
• 881662-21-1 1,3-diallyl amarine bromide 
• 484-47-9 lophine 
• 95000-92-3 2,4,5-tricyclohexyl-1H-imidazole 
• 102457-31-8 2,4r,5c-tricyclohexyl-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 
• 40102-64-5 racem.-1,2-diphenyl-ethane-1,2-diamine; dihydrochloride 
• 951-87-1 rac-1,2-diphenylethylene-1,2-diamine 
• 29841-69-8 (S,S)-1,2-diphenyl-1,2-diaminoethane 
• 911306-54-2 (+)-(1S,2S)-N-[(R)-α-acetoxyphenylacetyl]-N'-benzoyl-1,2-diamino-1,2-diphenylethane 
• 911306-52-0 (-)-(4S,5S)-1-[(R)-α-acetoxyphenylacetyl]-4,5-dihydro-2,4,5-triphenyl-1H-imidazole 
• 3190-22-5 erythro-N-benzoyl-N'-phenylmethylidene-1,2-diamino-1,2-diphenylethane 

Relevant articles and documents

Convenient one-step synthesis of cis-2,4,5-triarylimidazolines from aromatic aldehydes with urea

A simple and efficient method has been developed for the synthesis of cis-2,4,5-triarylimidazolines based on a one-step procedure of aldehydes and urea in the presence of cesium carbonate. Taylor & Francis Group, LLC.

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.

Cycloaddition reactions of 1,3-diazabuta-1,3-dienes with alkynyl ketenes

The cycloaddition reactions of 'all-carbon' 1,3-diazabuta-1,3-dienes with a few conjugated and unconjugated alkynyl ketenes are described. The reactions provide some interesting azetidinones and dihydropyrimidinones bearing an alkynyl moiety. The regiochemistry of cycloadduct is related with the degree of conjugation of the alkynyl ketene. Moreover, two alternative approaches to 'all-carbon' 1,3-diazabuta-1,3-dienes are reported.

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.

A convenient preparation of enantiomerically pure (+)-(1R,2R)- and (-)-(1S,2S)-1,2-diamino-1,2-diphenylethanes

A gram-scale preparation of (1S,2S)- and (1R,2R)-1,2-diamino-1,2- diphenylethanes, (1S,2S)-1 and (1R,2R)-1, is reported via (±)-iso-amarine 4. Strategically, the activation of (±)-iso-amarine 4 for hydrolysis to the required diamines and enantiomeric resolution is achieved simultaneously by formation of two separable diastereoisomeric N-acylamidines 5 and 6 derived from direct DCC-mediated coupling of (±)-iso-amarine 4 with (R)-acetylmandelic acid. iso-Amarine 4 is conveniently obtained from amarine 3, and a one-pot synthesis of the latter is reported from benzaldehyde and hexamethyldisilazane as catalysed by benzoic acid.

Alumina-ammonium acetate as an efficient reagent for the one-pot synthesis of cis-2,4,5-triarylimidazolines from aromatic aldehydes

A simple, efficient, and new method has been developed for the synthesis of 2,4,5-triarylimidazolines from aldehydes through a one-pot reaction of aldehydes in the presence of alumina-ammonium acetate under solvent-free conditions using microwave irradiation. This method is easy, rapid, one-pot and good to high-yielding reaction for the synthesis of 2,4,5-triarylimidazolines.

Synthesis and SAR of novel 4,5-diarylimidazolines as potent P2X7 receptor antagonists

The synthesis and SAR of a series of potent P2X7 receptor antagonists is described. The synthesis featured high-throughput solution- and solid-phase techniques including a microwave induced imidazoline formation. A series of 4,5-diarylimidazoline libraries were prepared using high-throughput solid-phase and microwave techniques. The compounds were evaluated as P2X 7 antagonists and their SAR is described.

Studies on the synthesis of 1-aminoalkylphosphonates from aldehydes using silica-supported ammonium hydrogen carbonate

Studies on the use of silica-supported ammonium hydrogen carbonate as an efficient reagent for the synthesis of 1-amino-phosphonates under microwave irradiation in solvent-free conditions is reported. Investigations showed that this reaction proceeds by the formation of methanediamine as an intermediate. The reaction in the absence of diethyl phosphite gave cis-imidazolines as the major products.

Synthesis of N,N-di(arylmethylidene)arylmethanediamines by flash vacuum pyrolysis of arylmethylazides

Flash vacuum pyrolysis of arylmethylazides 7a-d gave 2,4-diazapentadienes 5a-d in high yield (76-92%). The thermal cyclization of 5a-d gave cis-imidazolines 1a-d, further heating or Swern oxidation of 1a-d gave dehydrogenated products, imidazoles 2a-d.

Solvent-free efficient synthesis of 2,4,5-triarylimidazolines from aromatic aldehydes and hexamethyldisilazane

A one-step preparation of 2,4,5-triarylimidazolines from aromatic aldehydes was accomplished by heating with hexamethyldisilazane under solvent-free conditions. This reaction provides a convenient preparative method for triarylimidazolines having a variety of aryl groups.