1,3-Dibromo-5,5-dimethylhydantoin

Base Information

• Chemical Name: 1,3-Dibromo-5,5-dimethylhydantoin
• CAS No.: 77-48-5
• Deprecated CAS: 101650-80-0
• Molecular Formula: C5H6Br2N2O2
• Molecular Weight: 285.923
• Hs Code.: 2933.21 Oral rat LD50: 250 mg/kg
• European Community (EC) Number: 201-030-9
• NSC Number: 33305
• UNII: V9R5F9I7MZ
• DSSTox Substance ID: DTXSID3035341
• Nikkaji Number: J25.319G
• Wikipedia: DBDMH
• Wikidata: Q2078816
• ChEMBL ID: CHEMBL3184055
• Mol file: 77-48-5.mol

Synonyms:1,3-dibromo 5,5-dimethylhydantoin;1,3-dibromo-5,5-dimethylhydantoin;2,4-dibromo-5,5-dimethylhydantoin

Chemical Property of 1,3-Dibromo-5,5-dimethylhydantoin

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0.022mmHg at 25°C
• Melting Point: 197-199 °C (dec.)(lit.)
• Refractive Index: 1.621
• Boiling Point: 250.2 °C at 760 mmHg
• PKA: -3.44±0.40(Predicted)
• Flash Point: 105.1 °C
• PSA: 40.62000
• Density: 2.183 g/cm³
• LogP: 1.52480
• Storage Temp.: 0-6°C
• Sensitive.: Moisture Sensitive
• Solubility.: 1g/l
• Water Solubility.: Soluble in Alcohol, Ether, Benzene. Insoluble in Water.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 285.87755
• Heavy Atom Count: 11
• Complexity: 229

Purity/Quality:

99% ^*data from raw suppliers

1,3-Dibromo-5- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): O,C,N,Xi
• Hazard Codes: O,C,N,Xi
• Statements: 8-22-35-50/53-50-34
• Safety Statements: 17-26-36/37/39-45-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biocides/Disinfectants
• Canonical SMILES: CC1(C(=O)N(C(=O)N1Br)Br)C
• Uses: DBDMH is an important chemical product and has been widely applied in chemical, pharmaceutical and agricultural industries with various kinds of advantages including excellent stability, high content of bromine and high reactive activity. Currently, the combined formulation between DBDMH and other halogenated hydantoin for application has become a hotspot in recent years such as the combined application of BCDMH and DBDMH as well as the combined application of DCDMH and DBDMH. For the combined formulation of DBDMH and other halogenated hydantoin, one critical factor is the ratio between effective chlorine and effective bromine. For example, at pH 7.1, compound formulation with the same dose of BCDMH and DBDMH has a significantly higher bactericidal efficacy than DBDMH alone or BCDMH alone. Many domestic and foreign experts believe that the most significant oxidizing biocide is the compound halogenated compound formulation combining BCDMH and DBDMH. In agriculture, DBDMH is mainly used for aquaculture including pond disinfection, prevention of water disinfection, disease treatment, etc., and is not affected by water quality, salinity, pH, temperature, and other organic compounds during usage. In addition, there has been already cases in which people has applied DBDMH as high-efficiency and low-toxicity disinfectant for combined formulation with stearic acid monoglyceride and Tween-80 and applied to the surface of the orange for preventing mold and preservation, and has already achieved excellent results. We can expect that this preservative can also be used for storage and preservation of other fruits and vegetables. Therefore, with the continuous development of chemical and pharmaceutical industry and increasing people's living standards, it is expected that the application range and demand of DBDMH will increase greatly. Brominating agent. Analytical reagent for determination of iodide and organic iodine, and for identification tests. 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.
• Production method: It is obtained through the bromination of 5, 5-dimethyl hydantoin. Mix the 5, 5-dimethyl hydantoin, sodium carbonate, sodium hydroxide and water together, add bromine slowly under cooling. After the addition, it was poured into water with the crystal filtered out after standing being the crude product. The crude product was further dissolved in acetone for decolorizing and filtrating. The filtrate was poured into water to give white crystalline which is the finished product.

Technology Process of 1,3-Dibromo-5,5-dimethylhydantoin

There total 5 articles about 1,3-Dibromo-5,5-dimethylhydantoin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (77-48-5)

Guidance literature:

With bromine;

Reference yield: 97.0%

→ 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (77-48-5)

Guidance literature:

With [bis(acetoxy)iodo]benzene; In tetrachloromethane; at 20 ℃;

Reference yield:

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (77-48-5)

Guidance literature:

With sodium hydroxide; bromine; sodium carbonate;

upstream raw materials:

1,3-dichloro-5,5-dimethylhydantoin

5,5-dimethyl-imidazolidine-2,4-dione

sodium cyanide

acetone

Downstream raw materials:

Bromodiphenylmethane

9H-fluoren-9-yl bromide

4-Bromoveratrole

1-bromo-2-methoxynaphthalene

Refernces

• 1、 Huang, Hu,Pan, Hongjie,Cai, Yudong,Liu, Mao,Tian, Hua,Shi, Yian. "Enantioselective 6-endo bromoaminocyclization of 2,4-dienyl N-tosylcarbamates catalyzed by a chiral phosphine oxide-Sc(OTf)3 complex. A dramatic additive effect". . p. 3566 - 3570. Retrieved 2015.
• 2、 -. "PROCESS FOR THE PREPARATION OF ORGANIC BROMIDES". Paragraph 00114-00115;. . Retrieved 2017/07/28.