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425842

Sigma-Aldrich

4-Imidazolecarboxylic acid

98%

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About This Item

Fórmula empírica (notación de Hill):
C4H4N2O2
Número de CAS:
1072-84-0
Peso molecular:
112.09
EC Number:
214-017-8
MDL number:
MFCD00082203
UNSPSC Code:
12352005
PubChem Substance ID:
24866670
NACRES:
NA.22

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

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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.

Pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sigma-Aldrich

716537

Dimethyl 4,5-imidazoledicarboxylate

Francisco Aguilar-Pérez et al.
Inorganic chemistry, 45(23), 9502-9517 (2006-11-07)
The anion of 4-imidazolecarboxylic acid (HL) stabilizes hydroxo complexes of trivalent lanthanides of the type ML(OH)+ (M = La, Pr) and M2L(n)(OH)(6-n) (M = La, n = 2; M = Pr, n = 2, 3; M = Nd, Eu, Dy
Synthesis and catalytic properties of imidazole-functionalized poly (propylene imine) dendrimers.
Baker LA, et al.
Bull. Korean Chem. Soc., 23(5), 647-654 (2002)
Tetranuclear manganese carboxylate clusters with imidazole-carboxylate chelating ligands. X-ray crystal structure of the 4-imidazoleacetate complex.
Boskovic C, et al.
Polyhedron, 19(18), 2111-2118 (2000)
Diaquabis(1H-imidazole-4-carboxylato-κ2N3,O4) cobalt (II).
Chen WS.
Acta Crystallographica Section E, Structure Reports Online, 68(10), m1246-m1246 (2012)
Sci. Synth., 12, 325-325 (2002)
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