5,5-Dimethylhydantoin supplier

Name
5,5-Dimethylhydantoin
EINECS 201-051-3
CAS No. 77-71-4
Article Data51
CAS DataBase
Density 1.142 g/cm³
Solubility soluble in water
Melting Point 174-177 °C(lit.)
Formula C₅H₈N₂O₂
Boiling Point 237.54°C (rough estimate)
Molecular Weight 128.131
Flash Point 193oC
Transport Information
Appearance white to off-white crystals or crystalline powder
Safety 22-24/25-36/37-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Hydantoin,5,5-dimethyl- (6CI,7CI,8CI);4,4-Dimethyl-2,5-dioxoimidazolidine;5,5-Dimethyl-2,4-imidazolidinedione;DM Hydantoin;DMH;Dantoin 736;Dantoin DMH;Dimethylhydantoin;Fennosurf 300;NSC 8652;
PSA 58.20000
LogP 0.26200

Synthetic route

: 590-28-3
potassium cyanate

: 15028-41-8
methyl 2-aminoisobutyrate hydrochloride

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
Stage #1: potassium cyanate; methyl 2-aminoisobutyrate hydrochloride In water Milling; Green chemistry; Stage #2: With potassium carbonate In water Green chemistry;	92%

: potassium cyanide

: 506-87-6
ammonium carbonate

: 67-64-1
acetone

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
In water at 120℃; under 15001.5 Torr; for 0.533333h; Bucherer-Bergs Reaction; Flow reactor;	82%
Stage #1: potassium cyanide; ammonium carbonate; acetone In ethanol; water at 55 - 60℃; Bucherer-Bergs Reaction; Stage #2: With hydrogenchloride In ethanol; water	65%
Stage #1: acetone With sodium metabisulfite Stage #2: potassium cyanide Bucherer-Bergs reaction; Stage #3: ammonium carbonate Bucherer-Bergs reaction;
In ethanol; water at 50 - 80℃; Reflux;

...Expand

: 32786-02-0
2,3:4,5-bis-O-(isopropylidene)-D-fructopyranose aldehyde

ammonium carbonate: ammonium carbonate

A: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

B: 116730-70-2, 116730-73-5
3,4:5,6-di-O-isopropylidene-β-D-arabino-DL-glycero-3-heptulopyranosonitrile

C: 116730-72-4, 116730-76-8
3,4:5,6-di-O-isopropylidene-β-D-arabino-DL-glycero-3-heptulopyranosoamide

Conditions

Conditions	Yield
With potassium cyanide In ethanol; water at 50℃; for 72h;	A 77.8% B 2% C 7.3%

...Expand

: 116730-53-1
5-[(R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-eth-(Z)-ylidene]-imidazolidine-2,4-dione

A: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

B: 116730-55-3
5-(D-threo-2,3,4-trihydroxybutylidene)imidazol-2,4-dione

Conditions

Conditions	Yield
hydrolysis; Yield given;	A 62.5% B n/a

: 3673-15-2, 13039-93-5, 13039-94-6, 23568-31-2, 50866-82-5, 81801-10-7, 120522-08-9, 120522-09-0, 120522-10-3
2,3:4,5-di-O-isopropylidene-D-xylose

ammonium carbonate: ammonium carbonate

A: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

B: 116730-55-3
5-(D-threo-2,3,4-trihydroxybutylidene)imidazol-2,4-dione

Conditions

Conditions	Yield
With potassium cyanide In ethanol; water at 50℃; for 24h;	A 62.5% B 15%

...Expand

: 3673-15-2, 13039-93-5, 13039-94-6, 23568-31-2, 50866-82-5, 81801-10-7, 120522-08-9, 120522-09-0, 120522-10-3
2,3:4,5-di-O-isopropylidene-D-xylose

ammonium carbonate: ammonium carbonate

A: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

B: 116730-53-1
5-[(R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-eth-(Z)-ylidene]-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With potassium cyanide In ethanol; water at 50℃; for 24h;	A 62.5% B n/a

...Expand

: 463-79-6
carbonic-acid

: 19355-69-2
2-amino-2-cyanopropane

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
at 25℃; for 24h;	50%

: 4933-77-1
(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde

ammonium carbonate: ammonium carbonate

A: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

B: 116730-74-6, 116837-98-0
5-(4,5-isopropylidene-L-gluconor-L-mannono-nitrile-6-yl)hydantoin

C: 116730-68-8
5-<1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose-5(R)-yl>hydantoin

D: 116730-54-2, 116730-69-9
6-deoxy-1,2:3,4-di-O-isopropylidene-6-ureido-DL-glycero-α-D-galacto-heptopyranuronamide

Conditions

Conditions	Yield
With potassium cyanide In ethanol; water at 50℃; for 24h;	A 45% B 2% C 15.7% D 23%

...Expand

: 288-32-4
1H-imidazole

: 77-48-5
1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

A: 2302-25-2
4-bromo-1 H-imidazole

B: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With sulfuric acid In water at 0℃; for 0.0833333h;	A 21% B 33%

...Expand

: 5392-23-4
3,4-dihydro-4,4,6-trimethylpyrimidine-2(1H)-thione

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With potassium permanganate; water

: 16252-90-7
2-amino-2-methylpropanamide

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With ethanol; carbon dioxide

: 7505-93-3
2-cyano-2-methylpropanamide

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With potassium hypobromite

: 79662-84-3
(1-Cyan-1-methylethyl)harnstoff

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With hydrogenchloride

: 38605-63-9
N-carbamoyl-α-aminoisobutyric acid

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
at 130 - 140℃;
With hydrogenchloride
With hydrogenchloride at 50℃; Rate constant;

: 128326-91-0
ethyl 2-isocyanato-2-methylpropionate

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With ammonium hydroxide anschliessende Cyclisierung mit wss.HCl;

: 861329-91-1
dimethyl-malonic acid bis-bromoamide

: 124-41-4
sodium methylate

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
erst in der Kaelte, dann in der Hitze;

: 861329-91-1
dimethyl-malonic acid bis-bromoamide

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With sodium methylate

: 62-57-7
2-Aminoisobutyric acid

: 57-13-6
urea

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
at 160 - 170℃;

: 1111-78-0
ammonium carbamate

: 75-86-5
2-hydroxy-2-methylpropanenitrile

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
at 50 - 65℃;

: 143-33-9
sodium cyanide

: 67-64-1
acetone

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With ethanol; carbon dioxide; ammonia
With water; ammonium carbonate
With carbon dioxide; water; ammonium carbonate

: 151-50-8
potassium cyanide

: 67-64-1
acetone

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With hydrogenchloride; potassium cyanate
With water; ammonium carbonate
With hydrogenchloride; potassium cyanate
With carbon dioxide; water; ammonium carbonate

: 19355-69-2
2-amino-2-cyanopropane

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With carbon dioxide; water

: 7072-23-3
1,3-dibromo-5,5-dimethyl-hydantoin

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With hydrogenchloride; ascorbic acid In water at 30℃;

: 81587-19-1
(1-Carbamoyl-1-methyl-ethyl)-carbamic acid ethyl ester

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With sodium hydroxide In methanol for 1.5h; Ambient temperature;

: 73470-46-9
tert-butyl (1-amino-2-methyl-1-oxopropan-2-yl)carbamate

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With sodium hydroxide In methanol for 1.5h; Ambient temperature;

: 81587-18-0
benzyl N-(2-amino-1,1-dimethyl-2-oxo-ethyl)carbamate

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With sodium hydroxide In methanol for 1.5h; Ambient temperature;

: 104867-38-1
1,3-di(chlorothio)-5,5-dimethylhydantoin

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With water

: chlorohydantoin

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With arsenic(III); potassium iodide In water other reductants;

: 16079-88-2
N-bromo-N'-chloro-5,5-dimethylhydantoin

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With hydrogenchloride; potassium bromide; hydrazine In acetic acid at 32℃; Product distribution; other reductants;

: 110-91-8
morpholine

: 50-00-0
formaldehyd

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 951-13-3
5,5-Dimethyl-3-<(morpholin-4-yl)methyl>imidazolidin-2,4-dion

Conditions

Conditions	Yield
With 4 A molecular sieve In N,N-dimethyl-formamide for 15h; Ambient temperature;	100%
In methanol for 2h; Condensation;	98%
In ethanol	71%

...Expand

: 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%

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 118-52-5
1,3-dichloro-5,5-dimethylhydantoin

Conditions

Conditions	Yield
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With sodium carbonate at 20℃; for 6h; Stage #2: With chlorine In tetrahydrofuran; ethyl acetate at 100℃; for 7h; Concentration; Microwave irradiation;	98.72%
With trichloroisocyanuric acid In acetonitrile at 20℃; for 0.5h;	87%
With water; chlorine at 8 - 10℃;

: 66086-33-7
Di-tert-butyl acetylenedicarboxylate

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 603-35-0
triphenylphosphine

: di-tert-butyl 2-(4,4-dimethyl-2,5-dioxo-imidazolidin-1-yl)-3-(triphenylphosphanylidene)-succinate

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 8h;	98%

...Expand

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 17201-43-3
4-cyanobenzyl bromide

: 164648-32-2
4-((4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)methyl)benzonitrile

Conditions

Conditions	Yield
potassium tert-butylate	98%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	53.5%

: 101066-87-9
4-iodo-2-(trifluoromethyl)benzonitrile

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 143782-20-1
4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile

Conditions

Conditions	Yield
With copper(I) oxide In N,N-dimethyl-formamide at 150℃; for 12h;	98%
With copper(I) oxide In N,N-dimethyl-formamide at 150℃; for 12h;	98%
With copper(I) oxide In N,N-dimethyl-formamide at 150℃; for 14h; Inert atmosphere; regioselective reaction;	82%

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 100-51-6
benzyl alcohol

: 1886-18-6
3-benzoyl-5,5-dimethylimidazolidine-2,4-dione

Conditions

Conditions	Yield
With iron(III) chloride; calcium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate In water; acetonitrile at 35℃; for 1.5h; Sealed tube; Inert atmosphere;	98%

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: silver nitrate

: Ag(1+)*C5H7N2O2(1-)=AgC5H7N2O2

Conditions

Conditions	Yield
In not given	97%

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 286-20-4
cyclohexane-1,2-epoxide

: 40388-38-3
3-(2-hydroxy-cyclohexyl)-5,5-dimethyl-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With lithium chloride In N-methyl-acetamide	96.4%

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 16079-88-2
N-bromo-N'-chloro-5,5-dimethylhydantoin

Conditions

Conditions	Yield
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With bromine; sodium hydroxide In water at 5 - 10℃; for 0.25h; Large scale; Stage #2: With chlorine In water for 0.5h; Temperature; Reagent/catalyst; Large scale;	96.3%
With sodium hydroxide; bromine; chlorine In dichloromethane; water
With sodium hydroxide; bromine; chlorine In dichloromethane

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 66448-28-0
5,5-dimethyl-1,3-bis(TMS)hydantoin

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 15h; Heating;	96%

: 19614-67-6
N-(oxiran-2-ylmethyl)-N-ethylaniline

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 1258220-60-8
3-(5,5-dimethylhydantoin-3-yl)-1-(N-ethylanilino)propan-2-ol

Conditions

Conditions	Yield
In ethanol at 20 - 150℃; for 19h;	96%

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 693-02-7
hex-1-yne

: 3-[(Z)-hex-1-en-1-yl]-1,5,5-trimethylimidazolidine-2,4-dione

Conditions

Conditions	Yield
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 1,4-bis(dicyclohexylphosphino)butane; ytterbium(III) triflate In N,N-dimethyl-formamide at 60℃; for 16h; Inert atmosphere; optical yield given as %de;	96%

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 762-42-5
dimethyl acetylenedicarboxylate

: 603-35-0
triphenylphosphine

: dimethyl 2-(4,4-dimethyl-2,5-dioxo-imidazolidin-1-yl)-3-(triphenylphosphanylidene)-succinate

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 8h;	95%

...Expand

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 100-44-7
benzyl chloride

: 34657-68-6
3-benzyl-5,5-dimethyl-2,4-imidazolidinedione

Conditions

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃;	94%
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃;	94%
With sodium hydride In N,N-dimethyl-formamide for 15h; Ambient temperature;	53%

: 67-56-1
methanol

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 84039-99-6
methyl N-isopropylallophanate

Conditions

Conditions	Yield
for 30h; Irradiation;	93%

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 824-94-2
p-methoxybenzyl chloride

: 220615-80-5
3-(4-methoxybenzyl)-5,5-dimethylimidazolidine-2,4-dione

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 8h; Inert atmosphere;	93%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	88.5%
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With potassium hydroxide In ethanol at 25 - 90℃; Stage #2: p-methoxybenzyl chloride In methanol; ethanol at 25 - 60℃;	14%

: 4549-32-0
1,8-dibromooctane

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: C13H23BrN2O2

Conditions

Conditions	Yield
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: 1,8-dibromooctane In acetone at 20℃; for 3h;	92.4%
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With potassium carbonate In acetone for 0.5h; Reflux; Stage #2: 1,8-dibromooctane In acetone Reflux;	92.4%

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 106-95-6
allyl bromide

: 3366-92-5
1-(Prop-2-enyl)-4,4-dimethyl-2,5-dioxoimidazolidine

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water at 60℃; for 2h;	92%
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With sodium hydroxide In water Stage #2: allyl bromide In methanol; water at 60℃; for 1h;	90%
With triethylamine In tetrahydrofuran for 5h; Addition; Heating;

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 107-04-0
1-Bromo-2-chloroethane

: 53066-53-8
3-(2'-chloroethyl)-5, 5-dimethylhydantoin

Conditions

Conditions	Yield
With potassium hydroxide In ethanol at 80℃; for 8h;	92%
With potassium hydroxide In ethanol at 80℃; for 8h;	92%
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With sodium hydroxide In ethanol at 90℃; for 0.166667h; Stage #2: 1-Bromo-2-chloroethane In ethanol at 80℃; for 8h;	87.6%

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 535-11-5, 41978-69-2
Ethyl 2-bromopropionate

: 127834-98-4
2-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)propionic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 90h; Inert atmosphere; regioselective reaction;	92%

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 100-39-0
benzyl bromide

: 34657-68-6
3-benzyl-5,5-dimethyl-2,4-imidazolidinedione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 6h; Inert atmosphere; regioselective reaction;	92%
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With potassium carbonate In acetone for 0.5h; Reflux; Stage #2: benzyl bromide In acetone at 20℃; for 21h; Reflux;	73%

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 123726-16-9
bis(4-methylphenyl)iodonium trifluoromethanesulfonate

: 92668-56-9
5,5-dimethyl-3-(p-tolyl)imidazolidine-2,4-dione

Conditions

Conditions	Yield
With potassium phosphate; copper(l) iodide In 1,2-dichloro-ethane at 20℃; for 7h; Inert atmosphere; Schlenk technique; Sealed tube;	92%

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 100-39-0
benzyl bromide

A 3-benzyl-1-(3-iodo-2-propynyl-5,5-dimethylhydantoin: 3-benzyl-1-(3-iodo-2-propynyl-5,5-dimethylhydantoin

B: 34657-68-6
3-benzyl-5,5-dimethyl-2,4-imidazolidinedione

Conditions

Conditions	Yield
With potassium carbonate In acetone	A 91.3% B n/a

...Expand

: 580-13-2
2-bromonaphthalene

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 5,5-dimethyl-3-(naphthalen-2-yl)hydantoin

Conditions

Conditions	Yield
With copper(I) oxide In N,N-dimethyl-formamide at 150℃; for 14h; Inert atmosphere; regioselective reaction;	91%

: 5089-70-3
(3-chloropropyl)triethoxysilane

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 473780-80-2
5,5-dimethyl-3-(3'-triethoxysilylpropyl)hydantoin

Conditions

Conditions	Yield
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With potassium hydroxide In ethanol Heating / reflux; Stage #2: (3-chloropropyl)triethoxysilane In DMF (N,N-dimethyl-formamide) at 60 - 95℃; for 5h;	90.3%
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With sodium hydroxide In ethanol at 90℃; for 0.166667h; Stage #2: (3-chloropropyl)triethoxysilane In N,N-dimethyl-formamide at 95℃; for 10h;

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 2232-12-4
1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione

Conditions

Conditions	Yield
With sodium hypochlorite; iodine In acetic acid butyl ester; water at 10℃; for 2h; Solvent; Reagent/catalyst;	90%
With Iodine monochloride; sodium hydroxide In chloroform; water at -5 - 5℃; for 2h;	63.3%
With sodium hydroxide; Iodine monochloride In chloroform at 0℃; for 0.25h;	48%

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 1123-44-0
3-amino-5,5'-dimethylimidazolidine-2,4-dione

Conditions

Conditions	Yield
With hydrazine hydrate	90%
With hydrazine hydrate
With hydrazine hydrate Heating;
With hydrazine hydrate

5,5-Dimethylhydantoin Consensus Reports

Reported in EPA TSCA Inventory.

5,5-Dimethylhydantoin Specification

The IUPAC name of 5,5-Dimethylhydantoin is 5,5-dimethylimidazolidine-2,4-dione. With the CAS registry number 77-71-4, it is also named as 2,4-Imidazolidinedione, 5,5-dimethyl-; DM Hydantoin. The product's categories are miscellaneous natural products, water treatment chemicals, building blocks, heterocyclic building blocks and imidazolines / imidazolidines. It is white to off-white crystals or crystalline powder which is soluble in water, hexanol, ethyl acetate, dimethyl ether, slightly soluble in isopropylacetone, acetone, methyl ethyl ketone, and insoluble in aliphatic hydrocarbons, trichlorethylene.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.66; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.66; (4)ACD/LogD (pH 7.4): -0.66; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 10.46; (8)ACD/KOC (pH 7.4): 10.4; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.449; (13)Molar Refractivity: 30.11 cm³; (14)Molar Volume: 112.1 cm³; (15)Polarizability: 11.93×10^-24 cm³; (16)Surface Tension: 30.5 dyne/cm; (17)Tautomer Count: 5; (18)Exact Mass: 128.058578; (19)MonoIsotopic Mass: 128.058578; (20)Topological Polar Surface Area: 58.2; (21)Heavy Atom Count: 9.

Uses of 5,5-Dimethylhydantoin: It is not only used in the amino acid synthesis, but also as a special epoxy resins, water-soluble resin, fungicides, preservatives, etc. Its derivatives such as 1,3-dichloro-5,5-dimethyl hydantoin can be used as chlorination agent and sanitizers, and 3-hydroxymethyl-5,5-dimethyl hydantoin can be used as formaldehyde-based agents and preservatives. In addition, it can be used in organic synthesis. For example: 1. It reacts with chloromethyl-benzene to get 3-benzyl-5,5-dimethyl-imidazolidine-2,4-dione. This reaction needs reagent NaH and solvent dimethylformamide at ambient temperature. The reaction time is 15 hours. The yield is 53%.

2. It also can react with morpholine and formaldehyde to obtain 5,5-dimethyl-3-morpholin-4-ylmethyl-imidazolidine-2,4-dione. This reaction needs reagent molecular sieves (4 Angstroem) and solvent dimethylformamide at ambient temperature. The reaction time is 15 hours. The yield is 100%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. So people should not breathe dust and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing and gloves. This product must be stored in a tightly closed container which placed in a cool, dry area.

People can use the following data to convert to the molecule structure.
1. SMILES: O=C1NC(=O)NC1(C)C;
2. InChI: InChI=1/C5H8N2O2/c1-5(2)3(8)6-4(9)7-5/h1-2H3,(H2,6,7,8,9).

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LD50	oral	8430mg/kg (8430mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: WITHDRAWAL LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 47(6), Pg. 76, 1982.
guinea pig	LD50	unreported	5600mg/kg (5600mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 46(5), Pg. 69, 1981.
mammal (species unspecified)	LD50	unreported	15950mg/kg (15950mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 46(5), Pg. 69, 1981.
mouse	LD50	subcutaneous	2800mg/kg (2800mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 4, Pg. 723, 1954.
mouse	LD50	unreported	10gm/kg (10000mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 46(5), Pg. 69, 1981.
rabbit	LD50	oral	12660mg/kg (12660mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: REGIDITY	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 47(6), Pg. 76, 1982.
rat	LD50	oral	7800mg/kg (7800mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: WITHDRAWAL LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 47(6), Pg. 76, 1982.

Product Name

5,5-Dimethylhydantoin

Synthetic route

5,5-Dimethylhydantoin Consensus Reports

5,5-Dimethylhydantoin Specification

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