1-[2-(Trifluoromethyl)phenyl]imidazole

CAS Number 25371-96-4

Chemistry Building Blocks, Fluorinated Building Blocks, Heterocyclic Building Blocks, Monomers

1-[2-(Trifluoromethyl)phenyl]imidazole MSDS

1-[2-(Trifluoromethyl)phenyl]imidazole CAS 25371-96-4

A rigid fluorinated heterocyclic building block

Used as ligands and APIs in application of OLEDs, DSSCs and drug discovery

Overview
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1-[2-(Trifluoromethyl)phenyl]imidazole (CAS number 25371-96-4) is a trifluoromethyl substituted benzene ring connecting to an imidazole at ortho-position. By having a carbon-carbon single bond connected benzene and imidazole, 1-[2-(Trifluoromethyl)phenyl]imidazole shows strong binding affinity to transition metals such as iridium (Ir) and ruthenium (Ru). The homoleptic iridium(III)-phenylimidazole complexes show high photoluminescence quantum yields (53%) and in OLED devices they display high current efficiency of 20 cd/A at luminance of 1000 cd/m². A cyclometalated ruthenium complex with phenylimidazole is used as a chromogenic sensor for detecting fluoride in acetonitrile, showing a red shift from 565 nm to 618 nm (solution colour changed from red to green).

1-[2-(Trifluoromethyl)phenyl]imidazole has been vastly investigated as an inhibitor of neuronal nitric oxide synthase which is involved in depression and anxiety. 1-[2-(trifluoromethyl)phenyl]imidazole (30 mg/kg/day) shows significant antidepressant-like effect in vitro and in vivo study.

Multiple functional groups

For facile synthesis

Fluorinated imidazole building block

For drug discovery, biochemistry, and OLEDs

Worldwide shipping

Quick and reliable shipping

High purity

>98% High purity

General Information

CAS Number	25371-96-4
Chemical Formula	C₁₀H₇F₃N₂
Full Name	1-[2-(Trifluoromethyl)phenyl]-1H-imidazole
Molecular Weight	212.17 g/mol
Synonyms	TRIM, 1-(1H-Imidazol-1-yl)-2-(trifluoromethyl)benzene
Classification / Family	Fluorinated building block, Heterocyclic building block, OLEDs, APIs

Chemical Structure

Product Details

Purity	98%
Melting Point	T_m = 50 °C – 53 °C
Appearance	White powder

MSDS Documentation

1-[2-(Trifluoromethyl)phenyl]imidazole MSDS Sheet

Literature and Reviews

Effects of neuronal and inducible NOS inhibitor 1-[2-(trifluoromethyl)phenyl]imidazole (TRIM) in unpredictable chronic mild stress procedure in mice, O. Mutlu et al., Pharmacol. Biochem Behav., 92, 82-87(2009); DOI: 10.1016/j.pbb.2008.10.013.
A cycloruthenated 2phenylimidazole: chromogenic sensor for nitrite in acidic buffer and fluoride in CH₃CN, Z. Li et al., New J. Chem., 47, 4911-4919(2023); DOI: 10.1039/D2NJ05227J.
Homoleptic tris-cyclometalated iridium (III) complexes with phenylimidazole ligands for highly efficient sky-blue OLEDs, J. Zhuang et al., New J. Chem., 39, 246-253(2015); DOI: 10.1039/C4NJ01316F.
Ruthenium(II) bipyridyl complexes with cyclometalated NHC ligands, Inorg. Chem., 56(12), 7217–7229(2017); DOI: 10.1021/acs.inorgchem.7b00831.
The antinociceptive effect of 1-(2-trifluoromethylphenyl) imidazole (TRIM), a potent inhibitor of neuronal nitric oxide synthase in vitro, in the mouse, R. Handy et al., Br. J. Pharmacol., 116, 2349-2350(1995); DOI: 10.1111/j.1476-5381.1995.tb15078.x.

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