1,3-Dibromo-5,5-dimethylhydantoin

HCID 6479CAS 77-48-5

Basic information

Standard SMILES
CC1(C)C(=O)N(Br)C(=O)N1Br
InChIKey
VRLDVERQJMEPIF-UHFFFAOYSA-N
Molecular formula
C5H6Br2N2O2
Average molar mass
285.92 g/mol
Monoisotopic mass
283.87960163

Overview

1,3-Dibromo-5,5-dimethylhydantoin is an organobromide compound derived from the heterocycle called dimethylhydantoin. It is widely used as a disinfectant 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. Bromine is a halogen element with the symbol Br and atomic number 35. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock. (L625, L690)

Names & identifiers

Preferred name
1,3-Dibromo-5,5-dimethylhydantoin
IUPAC
1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione
English name
1,3-Dibromo-5,5-dimethylhydantoin
Molecular formula
C5H6Br2N2O2
Molecular weight
285.92

Names & synonyms

1,3-Dibromo-5,5-dimethylhydantoin77-48-5Dibromantin1,3-dibromo-5,5-dimethylimidazolidine-2,4-dioneDibromantineTake Charge OrangeDBDMHN,N'-Dibromodimethylhydantoin1,3-Dibromo-5,5-dimethyl-2,4-imidazolidinedione5,5-Dimethyl-1,3-dibromohydantoin2,4-Imidazolidinedione, 1,3-dibromo-5,5-dimethyl-DTXSID3035341
Show more names
DBNPADDHdibromohydantoinHSCDIBROMATIN
V9R5F9I7MZHYDANTOIN, 1,3-DIBROMO-5,5-DIMETHYL-NSC-33305DTXCID1015341DisinfectantTabletsDisinfectant TabletsRefChem:536271,3-dibromo 5,5-dimethylhydantoin

Database identifiers

CAS
77-48-5
PubChem CID
6479
DTXSID
DTXSID3035341
ChEMBL
CHEMBL3184055
UNII
V9R5F9I7MZ
EC Number
201-030-9
Nikkaji
J25.319G

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
40.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
11

Experimental & physicochemical properties

Chemical ClassesOther Uses -> Biocides/Disinfectants
Food Contact Substances · 2 items

FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications

FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications

Physical Description · 2 items

Dry Powder

Light yellow powder; [Aldrich MSDS]

Physicochemical properties

Melting point
197 · 197-199 °C (dec.)(lit.)
Boiling point
250.2 · 250.2±23.0 °C(Predicted)
Density
1 g/cm3 · 1.00 g/cm3 (25℃)
refractive index
1.622 · 1.6220 (estimate)
Flash point
155 °C · 155 °C
storage temp.
30 °C · Store below +30°C.

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H272 (93.5%): May intensify fire; oxidizer [Danger Oxidizing liquids; Oxidizing solids]

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, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 231 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: 2,4-Imidazolidinedione, 1,3-dibromo-5,5-dimethyl-

2,4-Imidazolidinedione, 1,3-dibromo-5,5-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,4-Imidazolidinedione, 1,3-dibromo-5,5-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 24-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/10089

1,3-Dibromo-5,5-dimethylhydantoin: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 item

Evidence of thyroid hypofunction in repeated dose study of rats; [RTECS] Corrosive to skin; Not sensitizing to guinea pigs; Halohydantoins: The persistent metabolites, 5,5-Dimethylhydantoin (DMH) and 5-Ethyl-5-methylhydantoin (EMH), are used for developing toxicity data for this group of compounds; Quickly decomposed by water forming hypochlorous or hypobromous acid (the true biocidal agents) and DMH or EMH; DMH/EMH: Sub-chronic, developmental, reproductive, and chronic toxicity animal studies have shown non-specific toxicity at high doses (no evidence of carcinogenicity, reproductive or developmental toxicity, and limited evidence of mutagenicity); [Reference #1] An oxidizer that can intensify fire; Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Toxic by ingestion; [Aldrich MSDS] See 1,3-Dichloro-5,5-dimethylhydantoin.

Hazard Classes and CategoriesOx. Sol. 3 (93.5%)

Toxicology

Treatment · 1 item

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Health Effects · 1 item

Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627)

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesOral (L626) ; inhalation (L626) ; dermal (L626)
Toxicity Summary · 1 item

Bromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (L626, L627, A543)

Signs and Symptoms · 1 item

Bromine vapour causes irritation and direct damage to the mucous membranes. Symptoms include lacrimation, rhinorrhoea, eye irritation with mucous secretions from the oropharyngeal and upper airways, coughing, dyspnoea, choking, wheezing, epistaxis, and headache. The bromide ion is a central nervous system depressant producing ataxia, slurred speech, tremor, nausea, vomiting, lethargy, dizziness, visual disturbances, unsteadiness, headaches, impaired memory and concentration, disorientation and hallucinations. This is called bromism. (L626, L627)

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
rtecs
MU0686000
ridadr
UN 3087 5.1/PG 2
hs_code
29332100

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Bromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (L626)

Uses & manufacturing

Uses · 3 items

Halohydantoins: Used as disinfectants in swimming pools, hot tubs, toilet bowls, and industrial systems (cooling water, pulp and paper, wastewater, and sewage); Also used as slimicide for paper/paperboard for food contact; [Reference #1]

Pulp and Paper Processing [Category: Industry]

1,3-Dibromo-5,5-dimethylhydantoin is an organobromide compound derived from the heterocycle called dimethylhydantoin. It is widely used as a disinfectant 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. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock.

U.S. Production2023: <75,000 lb
Industry UsesIntermediate
General Manufacturing Information · 2 items

Photographic Film, Paper, Plate, and Chemical Manufacturing

2,4-Imidazolidinedione, 1,3-dibromo-5,5-dimethyl-: ACTIVE

Applications · 4 items

Description1,3-Dibromo-5,5-dimethylhydantoin 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.

UsesIt 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.

UsesBrominating agent. Analytical reagent for determination of iodide and organic iodine, and for identification tests.

General DescriptionCurrently, the combined formulation between 1,3-Dibromo-5,5-dimethylhydantoin(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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海炎泽化工有限公司15345144255 19975051755 · [email protected]

Related reactions

408 records

Linked notes

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