1,3-Dibromo-5,5-dimethylhydantoin
[CAS# 77-48-5]

Identification

• Classification: API >> Synthetic anti-infective drugs >> Antiviral drugs
• Name: 1,3-Dibromo-5,5-dimethylhydantoin
• Synonyms: Dibromantin; Dibromo-5,5-dimethylhydantoin; 1,3-Dibromo-5,5-dimethyl-2,4-imidazolidinedione; DBNPA
• Molecular Formula: C₅H₆Br₂N₂O₂
• Molecular Weight: 285.92
• CAS Registry Number: 77-48-5
• EC Number: 201-030-9
• SMILES: CC1(C(=O)N(C(=O)N1Br)Br)C

Properties

• Density: 2.2±0.1 g/mL, Calc.^*
• Melting point: 197-199 °C (Expl.)
• Decomposition: 197-199 °C (Expl.)
• Index of Refraction: 1.622, Calc.^*
• Boiling Point: 250.2±23.0 °C (760 mmHg), Calc.^*
• Flash Point: 105.1±22.6 °C, Calc.^*, 155 °C (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS03;GHS05;GHS06;GHS07;GHS09 Danger
• Risk Statements: H272-H301-H302-H314-H315-H319-H400-H410
• Safety Statements: P210-P220-P260-P264-P264+P265-P270-P273-P280-P301+P316-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P321-P330-P332+P317-P337+P317-P362+P364-P363-P370+P378-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin irritation	Skin Irrit.	2	H315
Oxidising solids	Ox. Sol.	3	H272
Oxidising solids	Ox. Sol.	2	H272
Acute toxicity	Acute Tox.	3	H301
Skin corrosion	Skin Corr.	1A	H314
Skin corrosion	Skin Corr.	1B	H314
Skin sensitization	Skin Sens.	1	H317
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2A	H319
Oxidising liquids	Ox. Liq.	2	H272
Acute toxicity	Acute Tox.	1	H302
Oxidising liquids	Ox. Liq.	1	H272
Acute toxicity	Acute Tox.	3	H302

Discovery and Applications

1,3-Dibromo-5,5-dimethylhydantoin (DBDH) is an organic compound that belongs to the class of hydantoins, which are cyclic urea derivatives. It is widely used as a disinfectant and biocide, primarily in industrial and agricultural applications. The compound was first synthesized and characterized in the mid-20th century for its antimicrobial properties.

The structure of 1,3-dibromo-5,5-dimethylhydantoin consists of a hydantoin ring, which is a five-membered ring containing both nitrogen and carbon, with two bromine atoms attached to the 1 and 3 positions of the ring. This structure imparts the compound with its unique reactivity, particularly its ability to release bromine under certain conditions. The presence of bromine contributes to its bactericidal and fungicidal activities, making it effective as a disinfectant.

1,3-Dibromo-5,5-dimethylhydantoin is primarily used in water treatment applications, where it serves as a biocide to control microbial growth in cooling towers, industrial water systems, and swimming pools. Its ability to release bromine allows it to effectively kill a wide range of microorganisms, including bacteria, algae, and fungi. Additionally, it is utilized in the preservation of industrial processes that require controlled microbiological conditions.

The compound is also employed in agriculture as a fungicide and bactericide, particularly in the treatment of crops and agricultural equipment. By controlling the growth of harmful microorganisms, it helps in maintaining the health of plants and preventing crop diseases. Its use in post-harvest treatment helps in extending the shelf life of fruits and vegetables by reducing microbial contamination.

In addition to its use in disinfection and agriculture, 1,3-dibromo-5,5-dimethylhydantoin has applications in the production of other chemicals. It serves as a precursor in the synthesis of various organic compounds, including those used in polymerization reactions and other industrial processes. The compound’s ability to release bromine can also be utilized in chemical synthesis as a source of bromine atoms for substitution reactions.

While 1,3-dibromo-5,5-dimethylhydantoin is effective in its applications, safety precautions are necessary when handling the substance due to its toxic and corrosive nature. Proper storage and handling procedures are critical to minimize exposure to its potentially harmful effects.

In summary, 1,3-dibromo-5,5-dimethylhydantoin is an important biocide and disinfectant with various industrial and agricultural applications. Its ability to release bromine makes it effective in controlling microbial growth in water treatment, crop protection, and preservation. The compound continues to be a valuable tool in maintaining sanitary conditions in industrial, agricultural, and chemical processes.

References

2021. Poly-N-bromosulfonamide-melamine as a novel brominating reagent for regioselective ipso-bromination of arylboronic acids. Monatshefte für Chemie - Chemical Monthly, 152(8).
DOI: 10.1007/s00706-021-02827-2

2023. Mechanochemical synthesis of halogenated heterocyclic compounds. Chemistry of Heterocyclic Compounds, 59(8).
DOI: 10.1007/s10593-023-03227-6

2024. Bromination of naphtho[2,3-c][1,2,5]thiadiazole-4,9-dione. Russian Chemical Bulletin, 73(10).
DOI: