1-(Triphenylmethyl)imidazole

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1-(Triphenylmethyl)imidazole manufacturers

1-(Triphenylmethyl)imidazole Basic information
Product Name:1-(Triphenylmethyl)imidazole
Synonyms:N-TRITYLIMIDAZOLE;(TRIPHENYLMETHYL)IMIDAZOLE;1-(TRIPHENYLMETHYL)IMIDAZOLE;1-TRITYL-1H-IMIDAZOLE;1-TRITYLIMIDAZOLE;N-(Triphenylmethyl)imidazole;CDD 3501;Clotrimazole Impurity 6(Clotrimazole EP Impurity F)
CAS:15469-97-3
MF:C22H18N2
MW:310.39
EINECS:628-022-1
Product Categories:Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;blocks;Imidazoles;Building Blocks;Heterocyclic Building Blocks
Mol File:15469-97-3.mol
1-(Triphenylmethyl)imidazole Structure
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
pka6.34±0.30(Predicted)
color White to Off-White
Water Solubility Insoluble in water.
BRN 238171
InChIInChI=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
InChIKeyNPZDCTUDQYGYQD-UHFFFAOYSA-N
SMILESC1N(C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CN=1
CAS DataBase Reference15469-97-3(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
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
1-(Triphenylmethyl)imidazole Usage And Synthesis
Uses1-Tritylimidazole is a Clotrimazole (C587400) analog as antifungal agent.
Uses1-(Triphenylmethyl)imidazole may be used in the synthesis of 1,2,5-trisubstituted imidazole derivatives.
General Description1-(Triphenylmethyl)imidazole is an imidazole derivative.
Synthesis
Imidazole

288-32-4

Triphenylmethyl Chloride

76-83-5

1-(Triphenylmethyl)imidazole

15469-97-3

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
Tag: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 N-Fmoc-N'-Trityl-L-histidine pentafluorophenyl ester 3,5-DIIODO-D-TYROSINE HYDROCHLORIDE 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