56750

Imidazole

puriss. p.a., ≥99.5% (GC)

• Synonym(s): 1,3-Diaza-2,4-cyclopentadiene, Glyoxaline
• Empirical Formula (Hill Notation): C₃H₄N₂
• CAS Number: 288-32-4
• Molecular Weight: 68.08
• Beilstein/REAXYS Number: 103853
• EC Number: 206-019-2
• MDL number: MFCD00005183
• UNSPSC Code: 12352005
• eCl@ss: 39161001
• PubChem Substance ID: 57651598
• NACRES: NA.21

Properties

• vapor pressure: <1 mmHg ( 20 °C)
• Quality Level: 200
• grade: puriss. p.a.
• assay: ≥99.5% (GC)
• form: flakes; powder or crystals
• ign. residue (900°C): ≤0.1%
• pH: 9.5-11.0 (25 °C, 50 mg/mL in H₂O)
• pKa (25 °C): 6.95
• bp: 256 °C (lit.)
• mp: 88-91 °C (lit.); 88-91 °C
• solubility: alcohol: soluble(lit.); chloroform: soluble(lit.); pyridine: soluble(lit.); water: soluble(lit.)
• anion traces: chloride (Cl^-): ≤50 mg/kg; sulfate (SO₄^2-): ≤50 mg/kg
• cation traces: Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• SMILES string: c1c[nH]cn1
• InChI: 1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
• InChI key: RAXXELZNTBOGNW-UHFFFAOYSA-N

Description

General description

Imidazole is an aromatic heterocyclic compound with a five-membered planar ring. It is an amphoteric compound because of the presence of both an acidic NH and a basic nitrogen atom. Imidazole is an essential component of many important molecules including natural products, bioactive molecules, ionic liquids, and imidazolium. It serves as a building block for the synthesis of various drug molecules.

Application

Imidazole can be used as a catalyst:      

• For the silylation of alcohols, carboxylic acids, and amines in the presence of silyl chloride in DMF.     
• In the peptide coupling using the triphenyl phosphite.
• To prepare acid chlorides from the corresponding carboxylic acids and phosgene.

It can also be used in the following reactions:      

• Imidazole-PPh₃/I₂ catalytic system used in the conversion of alcohols into iodides      
• Imidazole-PPh₃/I₂ is used in the diol deoxygenation reaction.

Excellent for buffers in the range of pH 6.2-7.8

Other Notes

For titration of aspartic acid and glutamic acid

Safety Information

• pictograms: GHS05,GHS07,GHS08
• signalword: Danger
• hcodes: H302 - H314 - H360D
• pcodes: P260 - P280 - P301 + P312 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Dam. 1 - Repr. 1B - Skin Corr. 1C
• Storage Class: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 2
• flash_point_f: 293.0 °F - closed cup
• flash_point_c: 145 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges