1-(Triphenylmethyl)imidazole

1-(Triphenylmethyl)imidazole Property

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933299090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-(Triphenylmethyl)imidazole Chemical Properties,Usage,Production

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