• Name

  1,3-Dibromo-5,5-dimethylhydantoin

• EINECS 201-030-9
• CAS No. 77-48-5
• Article Data24
• CAS DataBase
• Density 2.183 g/cm³
• 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 285.923
• 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
• Hazard Symbols O,C,N,Xi
• 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);
• PSA 40.62000
• LogP 1.52480

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

Conditions	Yield
With bromine	99%
With bromine	99%
With bromine	99%

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

Conditions	Yield
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

Conditions	Yield
With water anschliessend mit wss.NaOH und Brom;

...Expand

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

106-25-2

Nerol

894806-14-5

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

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate; trifluoroacetic acid	79%

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

Conditions	Yield
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

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

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

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