2,4,5-Triphenylimidazole

Synonym(s):Lophine

CAS NO.：484-47-9
Empirical Formula: C21H16N2
Molecular Weight: 296.37
MDL number: MFCD00005187
EINECS: 207-606-6
SAFETY DATA SHEET (SDS)
Update Date: 2025-02-18 19:55:12

What is 2,4,5-Triphenylimidazole?

Description

Lophine (2,4,5-triphenyl-1H-imidazole) exhibits lemon yellow chemiluminescence in solution and is one of the few long-lasting chemiluminescent molecules. It forms dimers that have piezochromic and photochromic properties. It has been proposed as an analytical reagent for trace metal ion detection. Lophine’s chemiluminescence was discovered by B. Radziszewski in 1877.

Chemical properties

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The Uses of 2,4,5-Triphenylimidazole

2,4,5-Triphenylimidazole is used in the synthesis of fluorescent diarylethenes and nanowires of 2,4,5-triphenylimidazole, which finds application as single wire active optical waveguides and optically driven ultraviolet lasers.

Preparation

2,4,5-triphenylimidazole was synthesized by reaction between ammonia, benzaldehyde and benzoin: Benzoin (1) ( 5 g, 0.023 M) was reacted with benzaldehyde (5 mL, 0.05 mol) (2) in presence of ammonia (3) and refluxed for 4 h and the resulting mixture was cooled, filtered to get 2,4,5-triphenylimidazole (4).
Synthesis of 2,4,5-Triphenylimidazoles Novel Mannich Bases as Potential Antiinflammatory and Analgesic Agents
DOI: 10.3923/crc.2012.99.109

Properties of 2,4,5-Triphenylimidazole

Melting point:	274-278 °C (lit.)
Boiling point:	427.96°C (rough estimate)
Density	1.0874 (rough estimate)
refractive index	1.8000 (estimate)
storage temp.	Sealed in dry,Room Temperature
form	powder to crystal
pka	11.66±0.10(Predicted)
color	White to Orange to Green
Water Solubility	Soluble in methanol. Insoluble in water.
λmax	300nm(EtOH)(lit.)
BRN	236652
InChI	InChI=1S/C21H16N2/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/h1-15H,(H,22,23)
CAS DataBase Reference	484-47-9(CAS DataBase Reference)
EPA Substance Registry System	1H-Imidazole, 2,4,5-triphenyl- (484-47-9)

Safety information for 2,4,5-Triphenylimidazole

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05
GHS Hazard Statements	H314:Skin corrosion/irritation
Precautionary Statement Codes	P260:Do not breathe dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P363:Wash contaminated clothing before reuse. P301+P330+P331:IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P405:Store locked up. P501:Dispose of contents/container to..…