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1,3-Dibromo-5,5-dimethylhydantoin

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Name

1,3-Dibromo-5,5-dimethylhydantoin

EINECS 201-030-9
CAS No. 77-48-5 Density 2.183 g/cm3
PSA 40.62000 LogP 1.52480
Solubility Soluble in Alcohol, Ether, Benzene. Insoluble in Water. Melting Point 197-199 °C (dec.)(lit.)
Formula C5H6Br2N2O2 Boiling Point 250.2 °C at 760 mmHg
Molecular Weight 285.92 Flash Point 105.1 °C
Transport Information UN 3087 5.1/PG 2 Appearance white powder
Safety 17-26-36/37/39-45-60-61 Risk Codes 8-22-35-50/53-50-34
Molecular Structure Molecular Structure of 77-48-5 (1,3-Dibromo-5,5-dimethylhydantoin) Hazard Symbols OxidizingO,CorrosiveC,DangerousN,IrritantXi
Synonyms

1,3-Dibromo-5,5-dimethyl-2,4-imidazolidinedione;1,3-Dibromo-5,5-Dimethylhydantoin(DBDMH);2,4-Imidazolidinedione, 1, 3-dibromo-5,5-dimethyl-;Hydantoin, 1,3-dibromo-5,5-dimethyl-;5,5-Dimethyl-1,3-dibromohydantoin;2,4-Imidazolidinedione, 1,3-dibromo-5,5-dimethyl-;1,3-dibromo-5,5-dimethyl-imidazolidine-2,4-dione;Take Charge Orange;5-24-05-00374 (Beilstein Handbook Reference);Dibromantine;EPA Pesticide Chemical Code 006317;Dibromantin;2,4-Imidazolidinedione,1,3-dibromo-5,5- dimethyl-;Hydantoin, 1,3-dibromo-5,5-dimethyl- (8CI);N,N-Dibromodimethylhydantoin;1,3-Dibromo-5,5-Dimethyl hydantoin(DBDMH);

 

1,3-Dibromo-5,5-dimethylhydantoin Synthetic route

77-71-4

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

77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

Conditions
ConditionsYield
With bromine99%
With bromine99%
With bromine99%
118-52-5

1,3-dichloro-5,5-dimethylhydantoin

77-71-4

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

77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

Conditions
ConditionsYield
With sodium hydroxide; bromine; sodium carbonate
143-33-9

sodium cyanide

67-64-1

acetone

2CO3

2CO3

77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

Conditions
ConditionsYield
With water anschliessend mit wss.NaOH und Brom;
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

1521-38-6

2,3-dimethoxybenzoic acid

60555-93-3

6-bromo-2,3-dimethoxybenzoic acid

Conditions
ConditionsYield
With sodium hydroxide at 20℃;100%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

100-44-7

benzyl chloride

1444336-77-9

3-(benzyloxy)-6-bromo-2,4,5-trimethylpyridine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;97%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

C10H13F3N2O3

C10H12BrF3N2O3

Conditions
ConditionsYield
With bromine In dichloromethane at 15℃; for 24h;96.4%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

pinacol 4-(4-cyanophenoxy)-2-methylphenylborate

pinacol 4-(4-cyanophenoxy)-2-bromomethylphenylborate

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In chlorobenzene at 70 - 80℃; for 5h; Inert atmosphere;96%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

2700-23-4

4-Nitrobenzylidenemalononitrile

3-[2-bromo-2,2-dicyano-1-(4-nitrophenyl)]ethyl-5,5-dimethylhydantoin

Conditions
ConditionsYield
Stage #1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 4-Nitrobenzylidenemalononitrile With sodium hydrogencarbonate In acetonitrile at 20℃; for 7h;
Stage #2: With water; sodium sulfite In acetonitrile for 0.166667h;
94%
930596-87-5

3,7-dimethyl-3-methoxyoct-6-en-1-ol

77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

930596-89-7

6-bromo-3,7-dimethoxy-3,7-dimethyloctan-1-ol

Conditions
ConditionsYield
In methanol at 5 - 10℃;92%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

2700-22-3

Benzylidenemalononitrile

3-(2-bromo-2,2-dicyano-1-phenyl)ethyl-5,5-dimethylhydantoin

Conditions
ConditionsYield
Stage #1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; Benzylidenemalononitrile With sodium hydrogencarbonate In acetonitrile at 20℃; for 7h;
Stage #2: With water; sodium sulfite In acetonitrile for 0.166667h;
91%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

ethyl 2-(3-(difluoromethyl)-4,4a-dihydrospiro[cyclopropa[3,4]cyclopenta[1,2-c]pyrazole-5,2’-[1,3]dithiolane]-1(3bH)-yl)acetate

ethyl 2-(3-(difluoromethyl)-5,5-difluoro-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)acetate

Conditions
ConditionsYield
Stage #1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione With pyridine hydrogenfluoride In dichloromethane at -70℃; for 0.5h; Inert atmosphere;
Stage #2: ethyl 2-(3-(difluoromethyl)-4,4a-dihydrospiro[cyclopropa[3,4]cyclopenta[1,2-c]pyrazole-5,2’-[1,3]dithiolane]-1(3bH)-yl)acetate In dichloromethane at -40℃; for 1h;
91%
Stage #1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione With pyridine hydrogenfluoride In dichloromethane at -70℃; for 0.5h; Inert atmosphere;
Stage #2: ethyl 2-(3-(difluoromethyl)-4,4a-dihydrospiro[cyclopropa[3,4]cyclopenta[1,2-c]pyrazole-5,2’-[1,3]dithiolane]-1(3bH)-yl)acetate In dichloromethane at -70 - -40℃; for 1h;
91%
Stage #1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione With hydrogen fluoride In pyridine; dichloromethane at -78 - -8℃; for 1h;
Stage #2: ethyl 2-(3-(difluoromethyl)-4,4a-dihydrospiro[cyclopropa[3,4]cyclopenta[1,2-c]pyrazole-5,2’-[1,3]dithiolane]-1(3bH)-yl)acetate In pyridine; dichloromethane at -78 - -30℃; for 2.25h;
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

108-88-3

toluene

34657-68-6

3-benzyl-5,5-dimethyl-2,4-imidazolidinedione

Conditions
ConditionsYield
With copper(l) iodide; lithium bromide monohydrate; potassium carbonate; 1,2-bis-(diphenylphosphino)ethane at 120℃; for 24h; Inert atmosphere;91%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

2826-22-4

4-fluorobenzylidenemalononitrile

3-[2-bromo-2,2-dicyano-1-(4-fluorophenyl)]ethyl-5,5-dimethylhydantoin

Conditions
ConditionsYield
Stage #1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 4-fluorobenzylidenemalononitrile With sodium hydrogencarbonate In acetonitrile at 20℃; for 7h;
Stage #2: With water; sodium sulfite In acetonitrile for 0.166667h;
90%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

108-38-3

m-xylene

3-(3-methylbenzyl)-5,5-dimethylimidazolidine-2,4-dione

Conditions
ConditionsYield
With copper(l) iodide; lithium bromide monohydrate; potassium carbonate; 1,2-bis-(diphenylphosphino)ethane at 120℃; for 24h; Inert atmosphere;87%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

98-51-1

4-tert-butyltoluene

3-(4-tert-butylbenzyl)-5,5-dimethylimidazolidine-2,4-dione

Conditions
ConditionsYield
With copper(l) iodide; lithium bromide monohydrate; potassium carbonate; 1,2-bis-(diphenylphosphino)ethane at 140℃; for 6h; Inert atmosphere;86%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

894806-14-5

(2Z)-6-bromo-3,7-dimethyl-7-methoxyoct-2-en-1-ol

Conditions
ConditionsYield
In methanol at 5 - 10℃;85%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

19162-00-6

sulcatol acetate

930596-91-1

4-bromo-5-methoxy-1,5-dimethylhexyl acetate

Conditions
ConditionsYield
In methanol at 5 - 10℃;85%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

624-15-7

geraniol

(E/Z)-6-bromo-3,7-dimethyl-7-methoxyoct-2-en-1-ol

Conditions
ConditionsYield
In methanol at 5 - 10℃;85%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

98-86-2

acetophenone

1136548-61-2

5,5-dimethyl-3-(2-oxo-2-phenylethyl)imidazolidine-2,4-dione

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 12h;85%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

1975-50-4

2-methyl-3-nitrobenzic acid

107650-20-4

5-bromo-2-methyl-3-nitro-benzoic acid

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 5h;84%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

108-41-8

1-chloro-3-methylbenzene

3-(3-chlorobenzyl)-5,5-dimethylimidazolidine-2,4-dione

Conditions
ConditionsYield
With copper(l) iodide; lithium bromide monohydrate; potassium carbonate; 1,2-bis-(diphenylphosphino)ethane at 120℃; for 24h; Inert atmosphere;83%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

106-42-3

para-xylene

3-(4-methylbenzyl)-5,5-dimethylimidazolidine-2,4-dione

Conditions
ConditionsYield
With copper(l) iodide; lithium bromide monohydrate; potassium carbonate; 1,2-bis-(diphenylphosphino)ethane at 80℃; for 48h; Inert atmosphere;83%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

2826-26-8

2-(4-methoxyphenylmethylene)malononitrile

3-[2-bromo-2,2-dicyano-1-(4-methoxyphenyl)]ethyl-5,5-dimethylhydantoin

Conditions
ConditionsYield
Stage #1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2-(4-methoxyphenylmethylene)malononitrile With sodium hydrogencarbonate In acetonitrile at 20℃; for 24h;
Stage #2: With water; sodium sulfite In acetonitrile for 0.166667h;
82%
352-32-9

p-fluorotoluene

77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

860787-36-6

3-(4-fluorobenzyl)-5,5-dimethylimidazolidine-2,4-dione

Conditions
ConditionsYield
With copper(l) iodide; lithium bromide monohydrate; potassium carbonate; 1,2-bis-(diphenylphosphino)ethane at 120℃; for 24h; Inert atmosphere;81%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

106-43-4

para-chlorotoluene

3-(4-chlorobenzyl)-5,5-dimethylimidazolidine-2,4-dione

Conditions
ConditionsYield
With copper(l) iodide; lithium bromide monohydrate; potassium carbonate; 1,2-bis-(diphenylphosphino)ethane at 120℃; for 24h; Inert atmosphere;81%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

2826-25-7

2-(4-methylbenzylidene)malononitrile

3-[2-bromo-2,2-dicyano-1-(4-methlphenyl)]ethyl-5,5-dimethylhydantoin

Conditions
ConditionsYield
Stage #1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2-(4-methylbenzylidene)malononitrile With sodium hydrogencarbonate In acetonitrile at 20℃; for 7h;
Stage #2: With water; sodium sulfite In acetonitrile for 0.166667h;
80%

2-ethoxy-3-(trifluoromethyl)pyridine

77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

849934-83-4

5-bromo-2-ethoxy-3-trifluoromethyl-pyridine

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethyl acetate; trifluoroacetic acid79%
77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

26495-19-2

β,β-dicyano-3,5-dimethoxystyrene

3-[2-bromo-2,2-dicyano-1-(3,5-dimethoxyphenyl)]ethyl-5,5-dimethylhydantoin

Conditions
ConditionsYield
Stage #1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; β,β-dicyano-3,5-dimethoxystyrene With sodium hydrogencarbonate In acetonitrile at 20℃; for 10h;
Stage #2: With water; sodium sulfite In acetonitrile for 0.166667h;
78%

1,3-Dibromo-5,5-dimethylhydantoin Chemical Properties

Molecular structure of 1,3-Dibromo-5,5-dimethylhydantoin (CAS NO.77-48-5) is:

Product Name: 1,3-Dibromo-5,5-dimethylhydantoin
CAS Registry Number: 77-48-5
IUPAC Name: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione 
Molecular Weight: 285.92134 [g/mol]
Molecular Formula: C5H6Br2N2O2
XLogP3-AA: 1.5
H-Bond Donor: 0
H-Bond Acceptor: 2 
EINECS: 201-030-9
Melting Point: 197-199 °C (dec.)(lit.)
Sensitive: Moisture Sensitive
Surface Tension: 60.7 dyne/cm
Density: 2.183 g/cm3
Flash Point: 105.1 °C
Enthalpy of Vaporization: 48.74 kJ/mol
Boiling Point: 250.2 °C at 760 mmHg
Vapour Pressure: 0.022 mmHg at 25°C
Product Categories: Nitrogen cyclic compounds;Miscellaneous;Bromination;Halogenation;Synthetic Organic Chemistry;Water treatment chemicals

1,3-Dibromo-5,5-dimethylhydantoin Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LDLo skin 20gm/kg (20000mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0581-0382,
rat LCLo inhalation 29gm/m3/1H (29000mg/m3)   United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0281-0382,
rat LD50 oral 250mg/kg (250mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 36(10), Pg. 108, 1971.

1,3-Dibromo-5,5-dimethylhydantoin Safety Profile

Safty information about 1,3-Dibromo-5,5-dimethylhydantoin (CAS NO.77-48-5) is:
Hazard Codes: OxidizingO,CorrosiveC,DangerousN,IrritantXi
Risk Statements: 8-22-35-50/53-50-34 
R8 :Contact with combustible material may cause fire. 
R22:Harmful if swallowed. 
R35:Causes severe burns. 
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R34:Causes burns.
Safety Statements: 17-26-36/37/39-45-60-61 
S17:Keep away from combustible material. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S60:This material and its container must be disposed of as hazardous waste. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 3087 5.1/PG 2
WGK Germany: 3
RTECS: MU0686000
Hazard Note: Harmful/Irritant
HazardClass: 5.1
PackingGroup: II
HS Code: 29332100

1,3-Dibromo-5,5-dimethylhydantoin Specification

 1,3-Dibromo-5,5-dimethylhydantoin  , its cas register number is 77-48-5. It also can be called Dibromantin ; Dibromo-5,5-dimethylhydantoin ; 1,3-Dibromo-5,5-dimethyl-2,4-imidazolidinedione ; DBNPA .It is a white powder.

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