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425842 Sigma-Aldrich

4-Imidazolecarboxylic acid

98%

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Properties

Related Categories Building Blocks, C3 to C8, Chemical Synthesis, Heterocyclic Building Blocks, Imidazoles More...
Quality Level   100
assay   98%
mp   294-295 °C (lit.)
SMILES string   OC(=O)c1c[nH]cn1
InChI   1S/C4H4N2O2/c7-4(8)3-1-5-2-6-3/h1-2H,(H,5,6)(H,7,8)
InChI key   NKWCGTOZTHZDHB-UHFFFAOYSA-N

Description

General description

4-Imidazolecarboxylic acid (1H-imidazole-4-carboxylic acid, H2imc) is an imidazole derivative that contains an imidazole group and a carboxylate group. It has been widely utilized to generate different types of coordination polymers. The anion of 4-imidazolecarboxylic acid has been reported to stabilize binuclear hydroxo complexes of trivalent lanthanides in the pH range 7-10.

Application

4-Imidazolecarboxylic acid (ICA) was used in the synthesis of triphenymethyl-protected 4-imidazole carboxylic acid (trityl-ImCOOH) which is employed to functionalize poly(propylene imine) dendrimers.
It may be used in the following studies:
• In the synthesis of lanthanide sulfate–carboxylates, [Ln(HIMC)(SO4)(H2O)] (Ln = Dy and Eu, HIMC = 4-imidazolecarboxylic acid) by in situ decarboxylation in the presence of Cu(II) ions.
• As an internal standard to obtain calibration curve by plotting the peak area ratios of histamine (HA) and several metabolites isolated from C3H/HeNCrj mice hair relative to ICA.
• In the synthesis of tetranuclear manganese carboxylate complexes possessing imidazole-based N/O chelating ligands.

Packaging

1, 5 g in poly bottle

Other Notes

For a review of imidazoles, see Science of Synthesis.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
NI4001000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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