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CAS RN: 77-48-5 | Product Number: D1265

1,3-Dibromo-5,5-dimethylhydantoin


Purity: >97.0%(T)
Synonyms:
  • Dibromantin
  • DBDMH
Documents:
25G
£22.00
1   ≥20 
500G
£83.00
3   ≥20 

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Product Number D1265
Purity / Analysis Method >97.0%(T)
Molecular Formula / Molecular Weight C__5H__6Br__2N__2O__2 = 285.92  
Physical State (20 deg.C) Solid
Store Under Inert Gas Store under inert gas
Condition to Avoid Moisture Sensitive
CAS RN 77-48-5
Reaxys Registry Number 146024
PubChem Substance ID 87567800
SDBS (AIST Spectral DB) 4013
Merck Index (14) 3017
MDL Number

MFCD00003189

Specifications
Appearance White to Light red to Green powder to crystal
Purity(Iodometric Titration) min. 97.0 %
Solubility in hot Toluene almost transparency
Properties (reference)
Melting Point 193 °C
Boiling Point 376 °C
Solubility (soluble in) Chloroform,Ethanol
GHS
Pictogram Pictogram Pictogram Pictogram Pictogram
Signal Word Danger
Hazard Statements H301 : Toxic if swallowed.
H314 : Causes severe skin burns and eye damage.
H410 : Very toxic to aquatic life with long lasting effects.
oxidizer.
Precautionary Statements P273 : Avoid release to the environment.
P260 : Do not breathe dust or mist.
P220 : Keep away from clothing and other combustible materials.
P210 : Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish.
P391 : Collect spillage.
P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water.
P301 + P310 + P330 : IF SWALLOWED: Immediately call a POISON CENTER/doctor. Rinse mouth.
P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor.
P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.
Related Laws:
EC Number 201-030-9
RTECS# MU0686000
Transport Information:
UN Number UN3087
Class 5.1 / 6.1
Packing Group II
HS Number 2933210090
Application
Carbon-Heteroatom Bond Formation at the Benzylic Position of Methylarenes

D1265

Typical procedure (Ar = 4-BrPh, nucleophile = PhCO2H): To a solution of 4-bromotoluene (342.1 mg, 2.0 mmol) in anhydrous MeCN (4 mL) are added 1,3-dibromo-5,5-dimethylhydantoin (314.5 mg, 1.1 mmol) and AIBN (16.8 mg, 0.1 mmol) at room temperature. The mixture is stirred for 2 h at 90 °C. Then, benzoic acid (268.7 mg, 2.2 mmol) and DIPEA (0.35 mL, 2.0 mmol) are added at room temperature and the mixture is stirred for 16 h at 90 °C. The mixture is quenched by the addition of saturated aq. Na2SO3 solution (10 mL) and then extracted with CHCl3 (3 × 20 mL). The organic layer is dried over Na2SO4. After removal of the solvent under reduced pressure, the residue is purified by column chromatography on silica gel (eluent: hexane/CHCl3 = 1/1) to afford 4-bromobenzyl benzoate as a white solid. (489.1 mg, 84% yield).

References


Application
Selective ortho-Monobromination of Phenols and Polyphenols

Typical Procedure:
DBDMH (0.50–0.53 eq.) is added in part into the solution of starting material in CHCl3 (5–7 mL / mmol) at room temperature. Upon addition of the DBDMH, the solution becomes red or deep brown colored, the next portion of DBDMH is added after the disappearance of color and so on. The progress of the reaction is monitored by GC-MS. After completion of the reaction, removal of the solvent followed by the separation of the solid byproduct (derived from DBDMH) by simple filtration provides the almost pure bromide. 10% Aqueous sodium hydrosulfite solution is added into the reaction mixture, stirred for 5 min. Organic layer is separated, dried over MgSO4 and concentrated in evaporator yields the almost pure product. Passing through a small chromatographic column, it gives the pure products.

References

  • 1,3-Dibromo-5,5-dimethylhydantoin, a useful reagent for ortho-monobromination of phenols and polyphenols
    • A. Alam, Y. Takaguchi, S. Tsuboi, J. Fac. Environ. Sci. Tech., Okayama Univ. 2005, 10, 105.


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