bis(1H-imidazol-1-yl)ethane-1,2-dione

• ChemBase ID: 149876
• Molecular Formular: C8H6N4O2
• Molecular Mass: 190.15884
• Monoisotopic Mass: 190.04907545
• SMILES: c1cn(cn1)C(=O)C(=O)n1ccnc1
• Canonical SMILES: O=C(C(=O)n1cncc1)n1cncc1
• InChI: InChI=1S/C8H6N4O2/c13-7(11-3-1-9-5-11)8(14)12-4-2-10-6-12/h1-6H
• InChIKey: ONRNRVLJHFFBJG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(1H-imidazol-1-yl)ethane-1,2-dione
• IUPAC Traditional name: bis(imidazol-1-yl)ethane-1,2-dione
• Synonyms: Oxalic acid diimidazolide; 1,1′-Oxalyldiimidazole; Oxalic acid diimidazolide; 草酰基二咪唑; 1,1′-草酰基二咪唑; 草酰基二咪唑

Database IDs

• CAS Number: 18637-83-7
• MDL Number: MFCD00043067
• Beilstein Number: 611833
• PubChem SID: 24862655; 162244038
• PubChem CID: 100439

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -1.469201
• LogD (pH = 7.4): -1.4679068
• Log P: -1.4678904
• Molar Refractivity: 45.7174 cm^3
• Polarizability: 17.434572 Å^3
• Polar Surface Area: 69.78 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~115 °C; 114-116 °C(lit.)

Safety Information

• European Hazard Symbols: Corrosive (C)
• UN Number: 3259
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3
• Risk Statements: 21/22-34
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H312-H314
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3259 8/PG 3

Product Information

• Purity: ≥90% (NT)
• Grade: technical; technical grade
• Impurities: ≤10% free imidazole
• Empirical Formula (Hill Notation): C8H6N4O2

DETAILS

Sigma Aldrich - 366439

Other Notes
Contains imidazole
Packaging
5 g in glass bottle

Sigma Aldrich - 75749

Other Notes
Reagent for the activation of carboxylic acids: synthesis of esters, amides, anhydrides, etc.1,2,3; Conversion of oximes into nitriles4; Reagent for oxalylation of carbanions5