1H-imidazole-4-carboxylic acid

• ChemBase ID: 52861
• Molecular Formular: C4H4N2O2
• Molecular Mass: 112.08676
• Monoisotopic Mass: 112.02727738
• SMILES: c1nc(c[nH]1)C(=O)O
• Canonical SMILES: OC(=O)c1c[nH]cn1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H-imidazole-4-carboxylic acid; 1H-imidazole-5-carboxylic acid
• IUPAC Traditional name: 1H-imidazole-4-carboxylic acid; 3H-imidazole-4-carboxylic acid
• Synonyms: 1H-imidazole-5-carboxylic acid; 4-Imidazolecarboxylic acid; 1H-Imidazole-4-carboxylic acid; 4-Imidazolecarboxylic acid; 3H-Imidazole-4-carboxylic acid; 5-Carboxy-1H-imidazole; 1H-Imidazole-4-carboxylic acid; 4-Carboxy-1H-imidazole; 1H-Imidazole-5-carboxylic acid 98%; 1H-咪唑-4-甲酸

Database IDs

• CAS Number: 1072-84-0
• EC Number: 214-017-8
• MDL Number: MFCD00082203; MFCD01365907
• PubChem SID: 24866670; 162057624
• PubChem CID: 14080

CALCULATED PROPERTIES

• Acid pKa: 1.2403853
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.4695647
• LogD (pH = 7.4): -2.6302145
• Log P: -1.3808786
• Molar Refractivity: 25.897 cm^3
• Polarizability: 9.606815 Å^3
• Polar Surface Area: 65.98 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 259 - 261°C; 264-266°C; 294-295 °C(lit.)
• Hydrophobicity(logP): 0.567

Safety Information

• Storage Warning: IRRITANT; Irritant/Store under Argon
• RTECS: NI4001000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 95+%; 97%; 98%
• Empirical Formula (Hill Notation): C4H4N2O2

DETAILS

Sigma Aldrich - 425842

Application
Used in the synthesis of imidazole functionalized poly(propylene imine) dendrimers.1
Other Notes
For a review of imidazoles, see Science of Synthesis.2
Packaging
1 g in glass bottle
5 g in poly bottle