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About This Item
Empirical Formula (Hill Notation):
C4H4N2O2
CAS Number:
Molecular Weight:
112.09
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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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:
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
Certificates of Analysis (COA)
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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)
catena-Poly [copper (I)-bis [μ-3-(1H-imidazol-2-yl) pyridine]-copper (I)-di-μ-iodido].
425842
Acta Crystallographica Section E, Structure Reports Online, 67(9), 1288-1288 (2011)
Diaquabis(1H-imidazole-4-carboxylato-κ2N3,O4) cobalt (II).
Chen WS.
Acta Crystallographica Section E, Structure Reports Online, 68(10), m1246-m1246 (2012)
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