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

• ChemBase ID: 70259
• Molecular Formular: C5H6Br2N2O2
• Molecular Mass: 285.92134
• Monoisotopic Mass: 283.87960144
• SMILES: C1(N(C(=O)N(C1=O)Br)Br)(C)C
• Canonical SMILES: BrN1C(=O)N(C(C1=O)(C)C)Br
• InChI: InChI=1S/C5H6Br2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3
• InChIKey: VRLDVERQJMEPIF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione
• IUPAC Traditional name: dbdmh
• Synonyms: 1,3-Dibromo-5,5-dimethylimidazolidine-2,4-dione; Dibromantin; 1,3-Dibromo-5,5-dimethylhydantoin 98%; 1,3-Dibromo-5,5-dimethylhydantoin; Albrom 100, DBDMH; DibromantiH; DibromodimethylhydantoiH; XtraBrom 111; DBDMH; 1,3-Dibromo-5,5-dimethylhydantoin; 1,3-DIBROMO-5,5-DIMETHYLDANTOIN; DIBROMANTIN; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; Bromodan; 1,3-二溴-5,5-二甲基乙内酰脲; 1,3-二溴-5,5-二甲基海因; 1,3-二溴-5,5-二甲基乙内酰脲

Database IDs

• CAS Number: 77-48-5; 101650-80-0
• EC Number: 201-030-9
• MDL Number: MFCD00003189
• Beilstein Number: 146024
• PubChem SID: 162035982; 24860940; 24849707
• PubChem CID: 6479
• Chemspider ID: 6234
• Wikipedia Title: DBDMH

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.3758444
• LogD (pH = 7.4): 1.3758444
• Log P: 1.3758444
• Molar Refractivity: 46.1237 cm^3
• Polarizability: 17.967175 Å^3
• Polar Surface Area: 40.62 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 g/100 mL (20 °C) in water
• Apperance: White solid
• Melting Point: 197 - 199°C; 197-199 °C (dec.)(lit.); 197-199(dec.)°C; 197-203 °C; ca 198°C dec; ca 198°C dec.
• Flash Point: 155°C; 155°C(311°F)
• Density: 1.36 g/cm^3
• Hydrophobicity(logP): 1.133

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• Storage Warning: Moisture Sensitive; MOISTURE SENSITIVE, CORROSIVE, OXIDIZER; Oxidising/Toxic/Corrosive/Light Sensitive/Moisture Sensitive/Store under Argon
• RTECS: MU0686000
• European Hazard Symbols: Corrosive (C); Nature polluting (N); Oxidising (O); X
• UN Number: 3087; UN3085
• German water hazard class: 3
• Hazard Class: 5.1
• Packing Group: 2; II
• Risk Statements: 8-22-34-50; 8-22-35-50/53; R:22
• Safety Statements: 17-20-26-36/37/39-45-57; 17-26-36/37/39-45-60-61; R; S:36/37/39
• TSCA Listed: false; 是
• GHS Pictograms: GHS03; GHS05; GHS06; GHS07; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H272-H301-H314-H400; H272-H314-H318-H400-H302
• GHS Precautionary statements: P220-P273-P280-P301 + P310-P305 + P351 + P338-P310; P220-P273-P280-P305 + P351 + P338-P310; P221-P210-P303+P361+P353-P305+P351+P338-P405-P501A
• 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 3087 5.1/PG 2

Product Information

• Purity: ~98%; ≥97.0% (~55% active bromine, RT); 95%; 95+%; 97%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C5H6Br2N2O2

DETAILS

MP Biomedicals - 05214958

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02150853

Crystalline
Purity: ~98%
Selective brominating agent.

Sigma Aldrich - 157902

Packaging
25, 500 g in poly bottle
Application
Useful in aromatic bromination of alkoxybenzoic acids1 and in bromofluorination of alkenes.2

Sigma Aldrich - 34140

Other Notes
Bromination agent, used e.g. for a new α,β-enone-alkynone fragmentation1; Bromination of pyrrole2

REFERENCES

• Fehr, C., et al., Helv. Chim. Acta, 26: 2655 (1979).
• For use in combination with AgF as a reagent for the trans-fluorobromination of alkenes, see: Chem. Lett., 1877 (1988).
• Free-radical brominating agent: J. Chem. Soc., 4678 (1962), alternative to N-Bromosuccinimide, A15922, in many large-scale brominations. Superior to NBS for the regioselective free-radical 2-bromination of pyrrole: J. Org. Chem., 46, 2221 (1981); Org. Synth. Coll., 9, 121 (1998).
• Also behaves as a source of positive bromine. Electron-rich aromatic compounds undergo uncatalyzed ring-bromination: Tetrahedron Lett., 38, 4415 (1997). The bromination of less active substrates can be catalyzed by TMS triflate. Bromination of aromatic rings, including those with electron-withdrawing substituents, also occurs in the presence of strong acids: Bull. Chem. Soc. Jpn., 67, 1918 (1994). Has also been used as an alternative to NBS for the ring bromination of activated benzoic acids in the presence of aqueous NaOH: Tetrahedron Lett., 34, 931 (1993).