1-(Triphenylmethyl)imidazole Chemical Properties

Melting point:

220-224 °C(lit.)

Boiling point:

451.3±14.0 °C(Predicted)

Density 

1.05±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly, Sonicated), Methanol (Slightly, Sonicated)

form 

Solid

pka

6.34±0.30(Predicted)

color 

White to Off-White

Water Solubility 

Insoluble in water.

BRN 

238171

InChI

InChI=1S/C22H18N2/c1-4-10-19(11-5-1)22(24-17-16-23-18-24,20-12-6-2-7-13-20)21-14-8-3-9-15-21/h1-18H

InChIKey

NPZDCTUDQYGYQD-UHFFFAOYSA-N

SMILES

C1N(C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CN=1

CAS DataBase Reference

15469-97-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933299090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1-(Triphenylmethyl)imidazole Usage And Synthesis

Uses

1-(Triphenylmethyl)imidazole may be used in the synthesis of 1,2,5-trisubstituted imidazole derivatives.

Uses

1-Tritylimidazole is a Clotrimazole (C587400) analog as antifungal agent.

General Description

1-(Triphenylmethyl)imidazole is an imidazole derivative.

Synthesis

The reaction was carried out in a 50 L autoclave using imidazole (880 g, 12.9 mol, 1.0 eq.) and triphenylchloromethane (3605.0 g, 12.9 mol, 1.0 eq.) as raw materials. First, imidazole was dissolved in 12 L of DMF and cooled to below 0 °C. Subsequently, triethylamine (1308 g, 12.9 mol, 1.0 eq.) was added and the reaction was kept for 30 min. A DMF solution of triphenylchloromethane (16 L) was slowly added dropwise to the reaction mixture at 0°C. After the dropwise addition was completed, the reaction system was warmed to 15°C and the reaction was continued with stirring for 16 hours. Upon completion of the reaction, the reaction mixture was poured into water and a large amount of solid was precipitated. The solid was collected by filtration and the filter cake was washed with water, drained and dried to afford N-trityl imidazole (Compound XIV-1) as a white solid 3835.1 g in 95.6% yield.

References

[1] Patent: CN104086553, 2016, B. Location in patent: Paragraph 0065-0068
[2] Patent: US2010/16610, 2010, A1. Location in patent: Page/Page column 28
[3] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 253 - 256
[4] Tetrahedron, 1999, vol. 55, # 13, p. 4109 - 4122
[5] Patent: US6476216, 2002, B1

1-(Triphenylmethyl)imidazole(15469-97-3)Related Product Information

• Clotrimazole
• 1-Methylimidazole
• Imidazole
• 3-(Trifluoromethyl)benzaldehyde
• 5-Methyl-1H-benzotriazole
• Benzotrifluoride
• N-Fmoc-N'-trityl-D-histidine
• Fmoc-His(Trt)-OH
• FMOC-D-HIS(MTT)-OH
• N-FMOC-3-(triphenylmethyl)-L-histidine
• 3,5-DIIODO-D-TYROSINE HYDROCHLORIDE
• N-Fmoc-N'-Trityl-L-histidine pentafluorophenyl ester
• H-His(Trt)-OH
• 4-BROMO-1-TRITYL-1H-IMIDAZOLE
• Boc-His(Trt)-OH
• 2,5-DIBROMO-1-TRITYLIMIDAZOLE
• 4-Iodo-1-(triphenylmethyl)imidazole
• N-α-Fmoc-N-im-trityl-L-histidine N-carboxyanhydride