Imidazole CAS#288-32-4
Versatile Heterocyclic Building Block: Imidazole is an important five-membered aromatic heterocyclic compound widely used as a key intermediate in pharmaceutical, agrochemical, and fine chemical synthesis.
Unique Amphoteric Properties: With both acidic and basic characteristics, imidazole readily forms salts with strong bases and exhibits versatile chemical reactivity in a variety of synthesis processes.
Excellent Catalytic Performance: The imidazole ring combines the chemical features of pyridine and pyrrole, making it an effective catalytic and acyl-transfer structural unit in numerous chemical and biochemical reactions.
Biologically Significant Structure: Imidazole derivatives are widely found in biological systems, including important biomolecules such as histidine, DNA-related compounds, and hemoglobin, highlighting their broad scientific and industrial value.
Products Description of Imidazole CAS#288-32-4
Imidazole (molecular formula: C₃H₄N₂) is an organic compound belonging to the diazole family. It is a five-membered aromatic heterocyclic compound containing two non-adjacent nitrogen atoms within its ring structure. The lone pair of electrons on the nitrogen atom at the 1-position participates in cyclic conjugation, reducing the electron density of the nitrogen atom and allowing the hydrogen attached to it to be readily released as a proton.
Imidazole exhibits both acidic and basic properties and is capable of forming salts with strong bases. Its chemical behavior combines characteristics of both pyridine and pyrrole. In biological systems, the imidazole ring is an essential structural component of histidine, where it functions as an acyl-transfer group involved in lipid hydrolysis and plays an important catalytic role in enzymatic reactions. Imidazole derivatives are widely distributed in living organisms and are of greater significance than imidazole itself in scientific research and industrial applications, with important examples including DNA- and hemoglobin-related compounds.
Imidazole Chemical Properties
| Melting point | 88-91 °C(lit.) |
| Boiling point | 256 °C(lit.) |
| density | 1.01 g/mL at 20 °C |
| vapor pressure | <1 mm Hg ( 20 °C) |
| refractive index | 1.4801 |
| Fp | 293 °F |
| storage temp. | Store below +30°C. |
| solubility | H2O: 0.1 M at 20 °C, clear, colorless |
| pka | 6.953(at 25℃) |
| form | crystalline |
| color | white |
| Specific Gravity | 1.03 |
| Odor | Amine like |
| PH Range | 9.5 - 11 |
| PH | 9.5-11.0 (25℃, 50mg/mL in H2O) |
| Water Solubility | 633 g/L (20 ºC) |
| Sensitive | Hygroscopic |
| λmax | λ: 260 nm Amax: 0.10 |
| λ: 280 nm Amax: 0.10 | |
| Merck | 144912 |
| BRN | 103853 |
| Dielectric constant | 23.0（Ambient） |
| Stability: | Stable. Incompatible with acids, strong oxidizing agents. Protect from moisture. |
| InChIKey | RAXXELZNTBOGNW-UHFFFAOYSA-N |
| LogP | -0.02 at 25℃ |
| CAS DataBase Reference | 288-32-4(CAS DataBase Reference) |
| NIST Chemistry Reference | 1H-Imidazole(288-32-4) |
| EPA Substance Registry System | Imidazole (288-32-4) |
| Hazard Codes | C,Xi,T |
| Risk Statements | 36/38-63-34-22-20/21/22-61 |
| Safety Statements | 26-36/37/39-45-22-36-27-53 |
| RIDADR | UN 2923 8/PG 3 |
| WGK Germany | 1 |
| RTECS | NI3325000 |
| Autoignition Temperature | 480 °C |
| TSCA | Yes |
| HazardClass | 8 |
| PackingGroup | III |
| HS Code | 29332990 |
| Hazardous Substances Data | 288-32-4(Hazardous Substances Data) |
| Toxicity | LD50 in mice (mg/kg): 610 i.p.; 1880 orally (Nishie) |
Product Application of Imidazole CAS#288-32-4
Imidazole is slightly more basic than pyrazole and readily forms stable salts, including picrates and nitrates. One of its important applications is in the purification of His-tagged proteins using immobilized metal affinity chromatography (IMAC).
During the purification process, His-tagged proteins selectively bind to nickel ions immobilized on the chromatography resin. An imidazole-containing elution buffer is then used to compete with the His tag for nickel binding, allowing the target protein to be released from the column and collected with high purity.
