HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Compound

1,3-Dibromo-5,5-dimethylhydantoin

HCID 6479
New noteNew reactionRequest quotes
Print preview
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
77-48-5
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

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

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.
solubility
1 g/l · 1g/l
form
Powder

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

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.

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.

Related reactions

408 records
New reaction record
HRID 5774 reaction equation
HRID 5774As reactantuspto-grants-1993_09
HRID 6465 reaction equation
HRID 6465As reactantuspto-grants-1993_09
HRID 6466 reaction equation
HRID 6466As reactantuspto-grants-1993_09
HRID 37516 reaction equation
HRID 37516As reactantuspto-grants-1995_05
HRID 59580 reaction equation
HRID 59580As reactantuspto-grants-2016_09
HRID 60222 reaction equation
HRID 60222As reactantuspto-grants-2016_09
HRID 60230 reaction equation
HRID 60230As reactantuspto-grants-2016_09
HRID 60392 reaction equation
HRID 60392As reactantuspto-grants-2016_09
Page 1 of 51

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
New noteNew reactionRequest quotes
V9R5F9I7MZ
EC Number
201-030-9
Nikkaji
J25.319G
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)
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)

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

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

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

Sodium hypochlorite5,5-DimethylhydantoinHydrochloric acid1,3-Dichloro-5,5-dimethylhydantoinSodium cyanideSodium hydroxide

Downstream products

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