425842

4-Imidazolecarboxylic acid

98%

• Empirical Formula (Hill Notation): C₄H₄N₂O₂
• CAS Number: 1072-84-0
• Molecular Weight: 112.09
• EC Number: 214-017-8
• MDL number: MFCD00082203
• UNSPSC Code: 12352005
• PubChem Substance ID: 24866670
• NACRES: NA.22

Properties

• Quality Level: 100
• Assay: 98%
• mp: 294-295 °C (lit.)
• functional group: carboxylic acid
• 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.

Other Notes

For a review of imidazoles, see Science of Synthesis.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves