1-(1H-imidazol-1-yl)ethan-1-one

• ChemBase ID: 102998
• Molecular Formular: C5H6N2O
• Molecular Mass: 110.11394
• Monoisotopic Mass: 110.04801282
• SMILES: CC(=O)n1ccnc1
• Canonical SMILES: CC(=O)n1cncc1
• InChI: InChI=1S/C5H6N2O/c1-5(8)7-3-2-6-4-7/h2-4H,1H3
• InChIKey: VIHYIVKEECZGOU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(1H-imidazol-1-yl)ethan-1-one
• IUPAC Traditional name: acetylimidazole
• Synonyms: 1-Acetylimidazole; 1-Acetylimidazole; N-ACETYLIMIDAZOLE; 1-acetylimidazole; 1-乙酰基咪唑; N-乙酰基咪唑

Database IDs

• CAS Number: 2466-76-4
• EC Number: 219-577-7
• MDL Number: MFCD00005287
• Beilstein Number: 108425
• PubChem SID: 162090651; 24845151; 24849704
• PubChem CID: 17174

CALCULATED PROPERTIES

• Acid pKa: 19.84017
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.82617456
• LogD (pH = 7.4): -0.8254247
• Log P: -0.8254151
• Molar Refractivity: 28.2831 cm^3
• Polarizability: 10.8970175 Å^3
• Polar Surface Area: 34.89 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 100-104 °C; 98-104°C; 99-105 °C(lit.); 99-105°C

Safety Information

• Storage Condition: 0°C, Store Under Nitrogen
• Storage Warning: Moisture Sensitive
• RTECS: NI3400000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (GC); 98%
• Empirical Formula (Hill Notation): C5H6N2O

DETAILS

MP Biomedicals - 02150231

Crystalline
Selectively acetylates hydroxyl group of tyrosyl residues under conditions where most proteins are stable.
Also acetylates amino group of catecholamines prior to GLC.

Sigma Aldrich - 157864

Packaging
25, 100 g in glass bottle
Application
Relatively specific reagent for tyrosyl residue acetylation. Reagent used in the synthesis of annulated imidazole derivatives.

Sigma Aldrich - 01194

Other Notes
Acetylating agent1,2,3,4

REFERENCES

• Riordan, J.F., et al., Biochem. , 4 : 1758, (1965).
• Mild acylating agent. Reactivity can be enhanced by quaternization with, e.g. benzyl bromide: Chem. Pharm. Bull., 30, 4242 (1982). Acylation of nitromethane salts leads to acylnitro compounds: Synthesis, 478 (1978).