2,4-Imidazolidinedione, 3-methyl- supplier

Name
2,4-Imidazolidinedione, 3-methyl-
EINECS
CAS No. 6843-45-4
Article Data39
CAS DataBase
Density 1.285 g/cm³
Solubility
Melting Point
Formula C₄H₆N₂O₂
Boiling Point
Molecular Weight 114.104
Flash Point
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Hydantoin,3-methyl- (6CI,7CI,8CI);3-Methylhydantoin;3-Methylimidazolidine-2,4-dione;
PSA 49.41000
LogP -0.56530

Synthetic route

: 7150-62-1
ethyl (methylcarbamoyl)glycinate

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
With sodium methylate In methanol	85%
With hydrogenchloride In ethanol Heating; Yield given;
With sodium hydroxide In water Rate constant; Mechanism; other solvent, other base;
In methanol; water at 25℃; Rate constant; Mechanism; borax buffer (pH = 9.06, ionic strength 0.1), spectrophotometric measured;

: 94790-27-9
methyl {(methylcarbamoyl)amino}acetate

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
With sodium methylate In methanol	85%
With sodium hydroxide In water Rate constant; Mechanism; other solvent, other base;

: 461-72-3
2,4-imidazolidinedione

: 18871-66-4
N,N-dimethylacetamide dimethyl acetal

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
In toluene Heating;	73%
In toluene for 2h; Reflux;	68%
In toluene for 3h; Heating;	62%
In toluene at 110℃; for 2h;	50%
In toluene at 110℃; for 2h;

: 461-72-3
2,4-imidazolidinedione

: 77-78-1
dimethyl sulfate

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
With sodium hydroxide Heating;	55%
With sodium hydroxide Behandeln mit Salzsaeure unter vermindertem Druck;

: 131543-46-9
Glyoxal

: 598-50-5
N-Methylurea

A: 616-04-6
1-methyldiazolidine-2,4-dione

B: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
With 1-hydroxyethylene-(1,1-diphosphonic acid) In water at 90℃; for 2h; Green chemistry;	A 55% B 25%
Stage #1: Glyoxal With phosphorus pentoxide; water at 20℃; for 0.0833333h; Stage #2: N-Methylurea at 20℃; for 0.166667h;	A 45% B 20%

...Expand

: 71886-23-2
4-hydroxy-1-methyl-2,5-dioxo-4-imidazolidinecarboxyureide

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
With hydrogen iodide	52%

: 461-72-3
2,4-imidazolidinedione

: furan-2,3,5(4H)-trione pyridine (1:1)

: 77-78-1
dimethyl sulfate

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
Behandeln mit Salzsaeure unter vermindertem Druck;

...Expand

: 461-72-3
2,4-imidazolidinedione

: 74-88-4
methyl iodide

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
With potassium hydroxide
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 24h; Cooling with ice;	1.01 g

: 1-methyl-2,5-dioxo-imidazolidine-4-carboxylic acid

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
at 190℃;

: 556-61-6
methyl thioisocyanate

: 56-40-6
glycine

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
With potassium hydroxide Behandeln des Reaktionsprodukts mit Quecksilberoxyd anschliessend mit Salzsaeure;

: 56-40-6
glycine

: 598-50-5
N-Methylurea

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
at 130 - 140℃;

: 461-72-3
2,4-imidazolidinedione

: 74-88-4
methyl iodide

A: 6843-45-4
1-methylhydantoin

B: 24039-08-5
1,3-dimethylimidazolidine-2,4-dione

Conditions

Conditions	Yield
With aluminum oxide; potassium fluoride In acetonitrile for 24h; Ambient temperature; Yield given;

...Expand

: 56099-63-9
2-[(methylcarbamoyl)amino]acetic acid

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
With trifluoroacetic acid for 1h; Heating;
With sulfuric acid In water at 24.9℃; Rate constant; Mechanism; Thermodynamic data; ΔH(excit); ΔS(excit). Various temperatures, reagents and pH;

: 630112-53-7
1-carbamoyl-3-methylhydantoin

: 10034-85-2
hydrogen iodide

: 6843-45-4
1-methylhydantoin

: 22494-77-5
3-methyl-5-ureidohydantoin

: 10034-85-2
hydrogen iodide

: 6843-45-4
1-methylhydantoin

: 173038-91-0
1-(5-methoxy-3-methylhydantoin-5-carbonyl)-3-methylurea

: 10034-85-2
hydrogen iodide

: 6843-45-4
1-methylhydantoin

: 5-hydroxy-3-methyl-2,4-dioxo-imidazolidine-1-carboxylic acid nitroamide

: 10034-85-2
hydrogen iodide

: 6843-45-4
1-methylhydantoin

3-methyl-5-ethoxy-hydantoin-carboxylic acid-(5)-<α.ω-dimethyl ureide>: 3-methyl-5-ethoxy-hydantoin-carboxylic acid-(5)-<α.ω-dimethyl ureide>

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
With hydrogen iodide at 130℃;

3-methyl-5-ureido-hydantoin: 3-methyl-5-ureido-hydantoin

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
With hydrogen iodide

3-methyl-hydantoin-carboxylic acid-(5): 3-methyl-hydantoin-carboxylic acid-(5)

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
at 190℃;

9-methyl-uric acid glycol: 9-methyl-uric acid glycol

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
With hydrogen iodide

: 630112-53-7
1-carbamoyl-3-methylhydantoin

alkaline solution: alkaline solution

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
Behandeln mit Salzsaeure;

: 630112-53-7
1-carbamoyl-3-methylhydantoin

aq. barium hydroxide solution: aq. barium hydroxide solution

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
Behandeln mit Salzsaeure;

: 461-72-3
2,4-imidazolidinedione

: 74-88-4
methyl iodide

methanolic KOH-solution: methanolic KOH-solution

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
at 100℃;

...Expand

: 64759-44-0
1-methyl-3-(1-methyl-2,5-dioxo-imidazolidin-4-yl)-urea

: 10034-85-2
hydrogen iodide

phosphonium iodide: phosphonium iodide

: 6843-45-4
1-methylhydantoin

...Expand

: 3-methyl-2,4-dioxo-imidazolidine-1-carboxylic acid nitroamide

: 10034-85-2
hydrogen iodide

phosphonium iodide: phosphonium iodide

: 6843-45-4
1-methylhydantoin

...Expand

: N-(4-ethoxy-1-methyl-2,5-dioxo-imidazolidine-4-carbonyl)-N,N'-dimethyl-urea

: 10034-85-2
hydrogen iodide

phosphonium iodide: phosphonium iodide

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
at 130℃;

...Expand

: 74-88-4
methyl iodide

silver salt of hydantoin: silver salt of hydantoin

: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
at 110 - 120℃; im Rohr;

dimethyl-glycoluril: dimethyl-glycoluril

A: 616-04-6
1-methyldiazolidine-2,4-dione

B: 6843-45-4
1-methylhydantoin

Conditions

Conditions	Yield
With hydrogenchloride

: 6843-45-4
1-methylhydantoin

: 91-56-5
indole-2,3-dione

: 109-77-3
malononitrile

: (trans-3,7a')-5'-amino-2'-methyl-1',2,3'-trioxo-1',2',3',7a'-tetrahydrospiro[indoline-3,7'-pyrrolo[1,2-c]imidazole]-6'-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 80℃; diastereoselective reaction;	95%

...Expand

: 98-01-1
furfural

: 6843-45-4
1-methylhydantoin

: 109-77-3
malononitrile

: (trans-7,7a)-5-amino-7-(furan-2-yl)-2-methyl-1,3-dioxo-2,3,7,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazole-6-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 70℃; for 4h;	92%
With piperidine In water at 70℃; diastereoselective reaction;	92%

...Expand

: 98-03-3
thiophene-2-carbaldehyde

: 6843-45-4
1-methylhydantoin

: 109-77-3
malononitrile

: (trans-7,7a)-5-amino-2-methyl-1,3-dioxo-7-(thiophen-2-yl)-2,3,7,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazole-6-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 70℃; for 4h;	91%
With piperidine In water at 70℃; diastereoselective reaction;	91%

...Expand

: 6843-45-4
1-methylhydantoin

: 123-08-0
4-hydroxy-benzaldehyde

: 109-77-3
malononitrile

: (trans-7,7a)-5-amino-7-(4-hydroxyphenyl)-2-methyl-1,3-dioxo-2,3,7,7a-tetrahydro-1Hpyrrolo[1,2-c]imidazole-6-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 70℃; for 4h;	91%
With piperidine In water at 70℃; diastereoselective reaction;	91%

...Expand

: 6843-45-4
1-methylhydantoin

: 66440-60-6
1,5-dimethyl-1H-indole-2,3-dione

: 109-77-3
malononitrile

: (trans-3,7a')-5'-amino-1,2',5-trimethyl-1',2,3'-trioxo-1',2',3',7a'-tetrahydrospiro [indoline-3,7'-pyrrolo[1,2-c]imidazole]-6'-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 80℃; diastereoselective reaction;	91%

...Expand

: 6843-45-4
1-methylhydantoin

: 104-88-1
4-chlorobenzaldehyde

: 109-77-3
malononitrile

: (trans-7,7a)-5-amino-7-(4-chlorophenyl)-2-methyl-1,3-dioxo-2,3,7,7a-tetrahydro-1Hpyrrolo[1,2-c]imidazole-6-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 70℃; diastereoselective reaction;	90%
With piperidine In water at 70℃; for 5h;	87%

...Expand

: 6843-45-4
1-methylhydantoin

: 104-87-0
4-methyl-benzaldehyde

: 109-77-3
malononitrile

: (trans-7,7a)-5-amino-2-methyl-1,3-dioxo-7-(p-tolyl)-2,3,7,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazole-6-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 70℃; for 4h;	90%
With piperidine In water at 70℃; diastereoselective reaction;	90%

...Expand

: 6843-45-4
1-methylhydantoin

: 123-11-5
4-methoxy-benzaldehyde

: 109-77-3
malononitrile

: (trans-7,7a)-5-amino-7-(4-methoxyphenyl)-2-methyl-1,3-dioxo-2,3,7,7a-tetrahydro-1Hpyrrolo[1,2-c]imidazole-6-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 70℃; for 3.5h;	90%
With piperidine In water at 70℃; diastereoselective reaction;	90%

...Expand

: 6843-45-4
1-methylhydantoin

: 608-05-9
5-methyl-indole-2,3-dione

: 109-77-3
malononitrile

: (trans-3,7a')-5'-amino-2',5-dimethyl-1',2,3'-trioxo-1',2',3',7a'-tetrahydrospiro[indoline-3,7'-pyrrolo[1,2-c]imidazole]-6'-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 80℃; diastereoselective reaction;	90%

...Expand

: 6843-45-4
1-methylhydantoin

: 2058-74-4
1-methyl-1H-indole-2,3-dione

: 109-77-3
malononitrile

: (trans-3,7a')-5'-amino-1,2'-dimethyl-1',2,3'-trioxo-1',2',3',7a'-tetrahydrospiro[indoline-3,7'-pyrrolo[1,2-c]imidazole]-6'-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 80℃; diastereoselective reaction;	90%

...Expand

: 6843-45-4
1-methylhydantoin

: 830-74-0
1-allyl-1H-indole-2,3-dione

: 109-77-3
malononitrile

: (trans-3,7a')-1-allyl-5'-amino-2'-methyl-1',2,3'-trioxo-1',2',3',7a'-tetrahydrospiro-[indoline-3,7'-pyrrolo[1,2-c]imidazole]-6'-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 80℃; diastereoselective reaction;	89%

...Expand

: 6843-45-4
1-methylhydantoin

: 60434-13-1
5-chloro-1-methylindoline-2, 3-dione

: 109-77-3
malononitrile

: (trans-3,7a')-5'-amino-5-chloro-1,2'-dimethyl-1',2,3'-trioxo-1',2',3',7a'-tetrahydrospiro[indoline-3,7'-pyrrolo[1,2-c]imidazole]-6'-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 80℃; diastereoselective reaction;	89%

...Expand

: 6843-45-4
1-methylhydantoin

: 17630-76-1
5-chloroindole 2,3-dione

: 109-77-3
malononitrile

: (trans-3,7a')-5'-amino-5-chloro-2'-methyl-1',2,3'-trioxo-1',2',3',7a'-tetrahydrospiro[indoline-3,7'-pyrrolo[1,2-c]imidazole]-6'-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 80℃; diastereoselective reaction;	88%

...Expand

: 6843-45-4
1-methylhydantoin

: 773-91-1
5-fluoro-1-methylisatin

: 109-77-3
malononitrile

: (trans-3,7a')-5'-amino-5-fluoro-1,2'-dimethyl-1',2,3'-trioxo-1',2',3',7a'-tetrahydrospiro[indoline-3,7'-pyrrolo[1,2-c]imidazole]-6'-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 80℃; diastereoselective reaction;	88%

...Expand

: 6843-45-4
1-methylhydantoin

: 443-69-6
5-fluoro-1H-indole-2,3-dione

: 109-77-3
malononitrile

: (trans-3,7a')-5'-amino-5-fluoro-2'-methyl-1',2,3'-trioxo-1',2',3',7a'-tetrahydrospiro[indo-line-3,7'-pyrrolo[1,2-c]imidazole]-6'-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 80℃; diastereoselective reaction;	87%

...Expand

: 875003-43-3
7-fluoro-1-methyl-1H-indole-2,3-dione

: 6843-45-4
1-methylhydantoin

: 109-77-3
malononitrile

: (cis-3,7a')-5'-amino-7-fluoro-1,2'-dimethyl-1',2,3'-trioxo-1',2',3',7a'-tetrahydrospiro[indoline-3,7'-pyrrolo[1,2-c]imidazole]-6'-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 80℃; diastereoselective reaction;	87%

...Expand

: 6843-45-4
1-methylhydantoin

: 110-70-3
N,N`-dimethylethylenediamine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 72h; Heating; Argon;	85%

: 6843-45-4
1-methylhydantoin

: 89-98-5
2-chloro-benzaldehyde

: 88568-75-6
5-[1-(2-chlorophenyl)methylidene]-3-methylimidazolidine-2,4-dione

Conditions

Conditions	Yield
With potassium acetate; acetic anhydride In acetic acid for 16h; Heating;	85%

: 6843-45-4
1-methylhydantoin

: 87-48-9
5-Bromo-1H-indole-2,3-dione

: 109-77-3
malononitrile

: (trans-3,7a')-5'-amino-5-bromo-2'-methyl-1',2,3'-trioxo-1',2',3',7a'-tetrahydrospiro [indoline-3,7'-pyrrolo[1,2-c]imidazole]-6'-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 80℃; diastereoselective reaction;	81%

...Expand

: 6843-45-4
1-methylhydantoin

: 1122-91-4
4-bromo-benzaldehyde

: 109-77-3
malononitrile

: (trans-7,7a)-5-amino-7-(4-bromophenyl)-2-methyl-1,3-dioxo-2,3,7,7a-tetrahydro-tetrahydro-1H-pyrrolo[1,2-c]imidazole-6-carbonitrile

Conditions

Conditions	Yield
With piperidine In water at 70℃; for 4h;	80%
With piperidine In water at 70℃; diastereoselective reaction;	80%

...Expand

: 6843-45-4
1-methylhydantoin

: 20780-76-1
5-iodoisatin

: 109-77-3
malononitrile

: C15H10IN5O3

Conditions

Conditions	Yield
With piperidine In water at 80℃; diastereoselective reaction;	80%

...Expand

: 6843-45-4
1-methylhydantoin

: 115666-21-2
7-bromo-1 H-indole-3-carbaldehyde

: 5-((7-bromo-1H-indol-3-yl)methylene)-3-methylimidazolidine-2,4-dione

Conditions

Conditions	Yield
With piperidine at 110℃; for 6h; Sealed tube;	73%

: 6843-45-4
1-methylhydantoin

: 487-89-8
Indole-3-carboxaldehyde

: 200804-97-3
5-(1H-Indol-3-ylmethylene)-3-methylimidazolidine-2,4-dione

Conditions

Conditions	Yield
In piperidine at 110℃; for 4h;	71%

: 6843-45-4
1-methylhydantoin

: 4-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile

: (Z)-4-(7-(cyclopropylamino)-3-((1-methyl-2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile

Conditions

Conditions	Yield
With piperidine In ethanol at 80℃; for 15h;	68%
With piperidine In ethanol at 80℃; for 15h;	68%

: 6843-45-4
1-methylhydantoin

: 89-98-5
2-chloro-benzaldehyde

: 947396-30-7
5-[2-chlorophenyl(hydroxy)methyl]-3-methylimidazolidine-2,4-dione

Conditions

Conditions	Yield
With potassium acetate; acetic anhydride In acetic acid for 8h; Heating;	67%

: 6843-45-4
1-methylhydantoin

: 76782-82-6
tert-Butyldimethyl(prop-2-ynyloxy)silane

: 766549-73-9
5-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-1-methyl-1,3-dihydro-imidazol-2-one

Conditions

Conditions	Yield
Stage #1: 1-methylhydantoin; tert-Butyldimethyl(prop-2-ynyloxy)silane With butyl magnesium bromide In tetrahydrofuran Stage #2: With toluene-4-sulfonic acid In chloroform Further stages.;	62%

2,4-Imidazolidinedione, 3-methyl- Specification

The IUPAC name of 2,4-Imidazolidinedione, 3-methyl- is 3-methylimidazolidine-2,4-dione. With the CAS registry number 6843-45-4, it is also named as 3-Methylimidazolidine-2,4-dione. In addition, its molecular formula is C₄H₆N₂O₂ and molecular weight is 114.1026.

The other characteristics of 2,4-Imidazolidinedione, 3-methyl- can be summarized as: (1)# of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 9.585; (5)ACD/KOC (pH 7.4): 9.184; (6)#H bond acceptors: 4; (7)#H bond donors: 1; (8)#Freely Rotating Bonds: 0; (9)XLogP3-AA: -0.9; (10)Rotatable Bond Count: 0; (11)Tautomer Count: 4; (12)Exact Mass: 114.042927; (13)MonoIsotopic Mass: 114.042927; (14)Topological Polar Surface Area: 49.4; (15)Heavy Atom Count: 8; (16)Complexity: 143; (17)Polar Surface Area: 49.41 Å²; (18)Index of Refraction: 1.491; (19)Molar Refractivity: 25.719 cm³; (20)Molar Volume: 88.799 cm³; (21)Polarizability: 10.196×10^-24cm³; (22)Surface Tension: 41.558 dyne/cm; (23)Density: 1.285 g/cm³.

People can use the following data to convert to the molecule structure.
(1)SMILES: CN1C(=O)CNC1=O
(2)InChI: InChI=1/C4H6N2O2/c1-6-3(7)2-5-4(6)8/h2H2,1H3,(H,5,8)
(3)InChIKey: MZQQHYDUINOMDG-UHFFFAOYAU
(4)Std. InChI: InChI=1S/C4H6N2O2/c1-6-3(7)2-5-4(6)8/h2H2,1H3,(H,5,8)
(5)Std. InChIKey: MZQQHYDUINOMDG-UHFFFAOYSA-N

Product Name

2,4-Imidazolidinedione, 3-methyl-

Synthetic route

2,4-Imidazolidinedione, 3-methyl- Specification

Related Products

Hot Products