1H-Imidazole-4-carboxylic acid Chemical Properties

Melting point:

294-295 °C (lit.)

Boiling point:

495.0±18.0 °C(Predicted)

Density 

1.524±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Aqueous Acid (sparingly)

form 

Liquid

pka

2.69±0.10(Predicted)

color 

Clear colorless

InChI

InChI=1S/C4H4N2O2/c7-4(8)3-1-5-2-6-3/h1-2H,(H,5,6)(H,7,8)

InChIKey

NKWCGTOZTHZDHB-UHFFFAOYSA-N

SMILES

C1NC(C(O)=O)=CN=1

CAS DataBase Reference

1072-84-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

NI4001000

HazardClass 

IRRITANT

HS Code 

29332900

MSDS

• Language:English Provider:SigmaAldrich

1H-Imidazole-4-carboxylic acid Usage And Synthesis

Chemical Properties

Gray or tan powder

Uses

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.

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.

Synthesis

1. ethyl imidazole-4-carboxylate was mixed with potassium hydroxide solution at a mass ratio of 1:2.2, and the reaction was carried out at 30 °C. 2. After the reaction was completed, sulfuric acid solution was added slowly to adjust the pH of the reaction mixture to 1. 3. The crude product was purified by recrystallization to obtain 1H-imidazole-4-carboxylic acid.

References

[1] Patent: CN105693619, 2016, A. Location in patent: Paragraph 0010; 0088; 0089
[2] Patent: CN105622518, 2016, A. Location in patent: Paragraph 0083; 0094; 0095; 0096; 0097
[3] Patent: CN105622515, 2016, A. Location in patent: Paragraph 0074; 0075

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