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Dibrom-dimethylhydantoin

1,3-Dibromo-5,5-dimethylhydantoin

HCID 6479
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Grundinformationen

CAS
77-48-5
Standard-SMILES
CC1(C)C(=O)N(Br)C(=O)N1Br
InChIKey
VRLDVERQJMEPIF-UHFFFAOYSA-N
Summenformel
C5H6Br2N2O2
Durchschnittliche Molmasse
285,92 g/mol
Monoisotopische Masse
283,87960163

Überblick

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)

Namen und Bezeichner

Bevorzugter Name
1,3-Dibromo-5,5-dimethylhydantoin
IUPAC
1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione
Lokaler Name
Dibrom-dimethylhydantoin
Englischer Name
1,3-Dibromo-5,5-dimethylhydantoin
Summenformel
C5H6Br2N2O2
Molmasse
285.92

Namen und Synonyme

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
Weitere Namen anzeigen
DBNPADDHdibromohydantoinHSCDIBROMATIN
V9R5F9I7MZHYDANTOIN, 1,3-DIBROMO-5,5-DIMETHYL-NSC-33305DTXCID1015341DisinfectantTabletsDisinfectant TabletsRefChem:536271,3-dibromo 5,5-dimethylhydantoin

Datenbank-Bezeichner

CAS
77-48-5
PubChem CID
6479
DTXSID
DTXSID3035341
ChEMBL

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,5
Polarare Oberfläche (TPSA)
40,6 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
0
Schwere Atome
11
Formalladung
0
Komplexität
229

Experimentelle und physikochemische Eigenschaften

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

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

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

Physical Description · 2 Einträge

Dry Powder

Light yellow powder; [Aldrich MSDS]

Physikochemische Eigenschaften

Schmelzpunkt
197 · 197-199 °C (dec.)(lit.)
Siedepunkt
250.2 · 250.2±23.0 °C(Predicted)
Dichte
1 g/cm3 · 1.00 g/cm3 (25℃)
Brechungsindex
1.622 · 1.6220 (estimate)
Flammpunkt
155 °C · 155 °C
storage temp.
30 °C · Store below +30°C.
Löslichkeit
1 g/l · 1g/l
Aggregatzustand

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Regulatory Information · 4 Einträge

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 Eintrag

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.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

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)

Verwendung und Herstellung

Uses · 3 Einträge

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 Einträge

Photographic Film, Paper, Plate, and Chemical Manufacturing

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

Anwendungen · 2 Einträge

Beschreibung1,3-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.

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

Zugehörige Reaktionen

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Reaktionsgleichung von HRID 59580
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Reaktionsgleichung von HRID 60222
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Reaktionsgleichung von HRID 60230
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CHEMBL3184055
UNII
V9R5F9I7MZ
EC Number
201-030-9
Nikkaji
J25.319G
Powder
pka
-3.44 · -3.44±0.40(Predicted)
Farbe
Cream or light yellow
Wasserlöslichkeit
Soluble in Alcohol, Ether, Benzene. Insoluble in Water.
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 Datenbank
77 · 77-48-5(CAS DataBase Reference)
EPA chemische Informationen
1 · 1,3-Dibromo-5,5-dimethylhydantoin (77-48-5)
Hazard Classes and CategoriesOx. Sol. 3 (93.5%)

Toxikologische Informationen

Treatment · 1 Eintrag

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 Eintrag

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 Eintrag

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 Eintrag

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)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLC50 (rat) = 510 - 2,020 mg/m3

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
UN 3087 5.1/PG 2
hs_code
29332100
RTECS-Nr.
MU0686000
risk_code
8-22-35-50/53-50-34
hazard_code
O,C,N,Xi
hazard_note
Harmful/Irritant
safety_code
17-26-36/37/39-45-60-61
hazard_class
5.1
packing_group
II
Speicherklasse
5.1B - Oxidizing hazardous materials
Hazard Classifications
Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Ox. Sol. 3Skin Corr. 1BSkin Sens. 1
Selbstentzündungstemperatur
550°C
Verwenden

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Natriumhypochlorit5,5-DimethylhydantoinHydrogenchlorid1,3-Dichlor-5,5-dimethylhydantoinNatriumcyanidNatriumhydroxid

Nachgelagerte Produkte

1-Fluoro-4-(trifluoromethylthio)benzene5-Bromo-2-(dimethylamino)pyrimidine1,6-Dibromopyrene1-(Brommethyl)-3-phenoxybenzol