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77-48-5 - 1,3-Dibromo-5,5-dimethylhydantoin, 98% - Bromodan - Dibromantin - A15510 - Alfa Aesar

A15510 1,3-Dibromo-5,5-dimethylhydantoin, 98%

CAS Number
77-48-5
Synonyms
Bromodan
Dibromantin

Size Price ($) Quantity Availability
100g 18.09
500g 45.84
2500g 156.80
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1,3-Dibromo-5,5-dimethylhydantoin, 98%

MDL
MFCD00003189
EINECS
201-030-9

Chemical Properties

Formula
C5H6Br2N2O2
Formula Weight
285.93
Melting point
ca 198° dec.
Flash Point
155°(311°F)
Sensitivity
Moisture Sensitive
Solubility
Soluble in Alcohol, Ether, Benzene. Insoluble in Water.

Applications

It is used for drinking water purification, recreational water treatment, as a bleaching agent in pulp and paper mills, and for treating industrial/commercial water cooling systems. It is an efficient and selective agent for the oxidation of thiols to disulfides in solution or under solvent-free conditions.

Notes

Moisture sensitive. Store away from oxidizing agents, reducing agents, flammable substances, organic materials, metal powders & moisture.

Literature References

KHAZAEI Ardeshir, MOHAMMAD ALI ZOLFIGOL, ROSTAMI Amin. 1,3-dibromo-5,5-dimethylhydantoin [DBDMH] as an efficient and selective agent for the oxidation of thiols to disulfides in solution or under solvent-free conditions. Synthesis. 2004, 18 2959-2961.

Nelo R. Rivera; Jaume Balsells, Karl B. Hansen.Synthesis of 2-amino-5-substituted-1,3,4-oxadiazoles using 1,3-dibromo-5,5-dimethylhydantoin as oxidant. Tetrahedron Letters. 2006, 47 (28), 4889-4891.

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).

For use in combination with AgF as a reagent for the trans-fluorobromination of alkenes, see: Chem. Lett., 1877 (1988).

GHS Hazard and Precautionary Statements

Hazard Statements: H272-H314-H318-H400-H302

May intensify fire; oxidizer. Causes severe skin burns and eye damage. Causes serious eye damage. Very toxic to aquatic life. Harmful if swallowed.

Precautionary Statements: P221-P210-P260-P220-P273-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Take any precaution to avoid mixing with combustibles. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Keep/Store away from clothing/combustible materials. Avoid release to the environment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
146024
Hazard Class
5.1
Packing Group
II
Harmonized Tariff Code
2933.21
TSCA
Yes
RTECS
MU0686000

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