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
Show more names
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
- Formal charge
- 0
- Complexity
- 229
Experimental & physicochemical properties
Food Contact Substances
FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications
FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications
Physical Description
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.
- solubility
- 1 g/l · 1g/l
- form
- Powder
- pka
- -3.44 · -3.44±0.40(Predicted)
- color
- Cream or light yellow
- Water Solubility
- Soluble in Alcohol, Ether, Benzene. Insoluble in Water.
- Sensitive
- Moisture Sensitive
- Decomposition
- 197 · 197-199 ºC
- Merck
- 14 · 14,3017
- BRN
- 146024 · 146024
- InChI
- 1S/C5H6Br2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3
- InChIKey
- VRLDVERQJMEPIF-UHFFFAOYSA-N
- SMILES
- CC1(C)N(Br)C(=O)N(Br)C1=O
- CAS DataBase Reference
- 77 · 77-48-5(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 9 R5F9I7MZ · V9R5F9I7MZ
- EPA Substance Registry System
- 1 · 1,3-Dibromo-5,5-dimethylhydantoin (77-48-5)
- Pesticides Freedom of Information Act (FOIA)
- 1 · 1,3-Dibromo-5,5-dimethylhydantoin
- UNSPSC Code
- 12352115 · 12352115
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 3 · GHS03,GHS05,GHS06,GHS09
- Signal word
- Danger
- Hazard statements
- 272 · H272-H301-H314-H317-H400
- Precautionary statements
- 210 · P210-P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- O,C,N,Xi
- Risk Statements
- 8 · 8-22-35-50/53-50-34
- Safety Statements
- 17 · 17-26-36/37/39-45-60-61
- RIDADR
- 3087 · UN 3087 5.1/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 686000 · MU0686000
- Autoignition Temperature
- 550 °C · 550°C
- Hazard Note
- Harmful/Irritant
- TSCA
- TSCA listed
- HazardClass
- 5.1 · 5.1
- PackingGroup
- II
- HS Code
- 29332100 · 29332100
- Storage Class
- 5.1 B · 5.1B - Oxidizing hazardous materials
- Hazard Classifications
- 3 OralAquatic · Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Ox. Sol. 3Skin Corr. 1BSkin Sens. 1
- REACH Registrations
- Active
- Limited Quantities
- 1 kg · 1.0 kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
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
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
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.
Toxicology
Treatment
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
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)
Toxicity Summary
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
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
- risk_code
- 8-22-35-50/53-50-34
- Signal word
- Danger
- Symbol(GHS)
- GHS03,GHS05,GHS06,GHS09
- hazard_code
- O,C,N,Xi
- hazard_note
- Harmful/Irritant
- safety_code
- 17-26-36/37/39-45-60-61
- hazard_class
- 5.1
- Storage Class
- 5.1B - Oxidizing hazardous materials
- packing_group
- II
- Hazard statements
- H272-H301-H314-H317-H400
- Limited Quantities
- 1.0 kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Ox. Sol. 3Skin Corr. 1BSkin Sens. 1
- Autoignition Temperature
- 550°C
- Precautionary statements
- P210-P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Chemistry & industry
Pharmacology
Metabolism/Metabolites
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
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.
General Manufacturing Information
Photographic Film, Paper, Plate, and Chemical Manufacturing
2,4-Imidazolidinedione, 1,3-dibromo-5,5-dimethyl-: ACTIVE
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
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