1,3-diiodo-5,5-dimethylimidazolidine-2,4-dione

• ChemBase ID: 142556
• Molecular Formular: C5H6I2N2O2
• Molecular Mass: 379.92228
• Monoisotopic Mass: 379.85187344
• SMILES: CC1(C(=O)N(C(=O)N1I)I)C
• Canonical SMILES: IN1C(=O)N(C(C1=O)(C)C)I
• InChI: InChI=1S/C5H6I2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3
• InChIKey: RDZHCKRAHUPIFK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-diiodo-5,5-dimethylimidazolidine-2,4-dione
• IUPAC Traditional name: 1,3-diiodo-5,5-dimethylimidazolidine-2,4-dione
• Synonyms: DIH; 1,3-Diiodo-5,5-dimethylhydantoin; 1,3-Diiodo-5,5-dimethyl hydantoin; 1,3-二碘-5,5-二甲基海因

Database IDs

• CAS Number: 2232-12-4
• MDL Number: MFCD00020867
• Beilstein Number: 146040
• PubChem SID: 162236783
• PubChem CID: 200534

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.3503593
• LogD (pH = 7.4): 1.3503593
• Log P: 1.3503593
• Molar Refractivity: 55.3349 cm^3
• Polarizability: 22.700909 Å^3
• Polar Surface Area: 40.62 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: MU0970000
• European Hazard Symbols: Corrosive (C); Nature polluting (N); Oxidising (O)
• German water hazard class: 3
• Risk Statements: 8-35-50/53
• Safety Statements: 26-36/37/39-45-60-61
• GHS Pictograms: GHS03; GHS05; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H272-H314-H400
• GHS Precautionary statements: P220-P273-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
• Storage Temperature: -20°C

Product Information

• Purity: ≥96%; 95+%; 98%
• Empirical Formula (Hill Notation): C5H6I2N2O2

DETAILS

Sigma Aldrich - 711624

Packaging
5, 25 g in glass bottle
Application
DIH - Highly efficient and economical reagent for IodinationUsed for:
• Preparation of nitriles from corresponding alcohols and amines via oxidative conversion1
• Chemoselective, stereospecific iododesilylation of silylated alkenes2
• Preparation of N-benzyl toluenesulfonamides via sulfonylamidation of alkylbenzenes with toluenesulfonamide in presence of diiododimethylhydantoin3
• Iodination reactions4