1H-Imidazole-2-carboxylic acid Chemical Properties

Melting point:

198 °C

Boiling point:

407.9±28.0 °C(Predicted)

Density 

1.524±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

powder to crystal

pka

1.44±0.10(Predicted)

color 

White to Dark blue

λmax

247nm(lit.)

BRN 

112615

InChI

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

InChIKey

KYWMCFOWDYFYLV-UHFFFAOYSA-N

SMILES

OC(=O)c1ncc[nH]1

CAS DataBase Reference

16042-25-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

22-26-36/37/39-36

WGK Germany 

WGK 3

HazardClass 

IRRITANT

HS Code 

2933299090

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Dam. 1

1H-Imidazole-2-carboxylic acid Usage And Synthesis

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 1090, 1995 DOI: 10.1021/jo00109a052

Synthesis

General procedure for the synthesis of imidazole-2-carboxylic acid from 2-imidazolecarboxaldehyde: 30% aqueous H2O2 solution (10 g) was slowly added dropwise to stirred aqueous 2-imidazolecarboxaldehyde (2.88 g, 0.030 mol) solution (10 ml). The reaction was continued at room temperature for 72 hours. After completion of the reaction, water was removed by distillation under reduced pressure at room temperature to give a white crystalline solid. The resulting solid was washed with stirred diethyl ether/water (4:1) mixture to remove residual peroxide. Note: Heating may cause decarboxylation to occur. The yield was 97.5%. Melting point (MP) was 156-158 °C. 1H NMR (400 MHz, D2O): δ 7.56 (2H, s, imidazolium ring-H); 13C NMR (400 MHz, D2O): δ 158.86, 141.02, 120.49 ppm. IR (KBr, cm-1): 3392 (m), 3124 (m), 2861 ( m), 1618 (s), 1502 (m), 1462 (m), 1421 (s), 1388 (s), 1322 (m), 1108 (s), 925 (s), 910 (s), 819 (m), 797 (s), 774 (m). Calculated values for elemental analysis (C4H6N2O3, 130.11): C, 36.92%; H, 4.65%; N, 21.53%. Measured values: C, 37.18%; H, 4.94%; N, 21.47%.

References

[1] Journal of Inorganic Biochemistry, 2015, vol. 145, p. 11 - 18

1H-Imidazole-2-carboxylic acid(16042-25-4)Related Product Information

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