• Name

  5-(2-Methylthioethyl)hydantoin

• EINECS 236-238-9
• CAS No. 13253-44-6
• Article Data29
• CAS DataBase
• Density 1.228g/cm³
• Solubility
• Melting Point 108°C
• Formula C6H10 N2 O2 S
• Boiling Point °Cat760mmHg
• Molecular Weight 174.224
• Flash Point °C
• Transport Information
• Appearance
• Safety Low toxicity by ingestion and skin contact. When heated to decomposition it emits toxic vapors of NO_x and SO_x.
• Risk Codes
• Molecular Structure
• Hazard Symbols Low toxicity by ingestion and skin contact.
• Synonyms Hydantoin,5-[2-(methylthio)ethyl]- (6CI,7CI,8CI); (?à)-5-[2-(Methylthio)ethyl]hydantoin; 5-(b-Methylmercaptoethyl)hydantoin;5-[2-(Methylthio)ethyl]hydantoin; 5-[b-(Methylthio)ethyl]hydantoin; DL-5-(b-Methylmercaptoethyl)hydantoin;DL-5-[2-(Methylthio)ethyl]hydantoin; Methionine hydantoin
• PSA 83.50000
• LogP 0.60510

Synthetic route

17773-41-0

2-hydroxy-4-(methylthio)butyronitrile

ammonium bicarbonate

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

Conditions

Conditions	Yield
In water at 80℃; for 2h;	99%

773837-37-9

sodium cyanide

42919-64-2

4-(methylthio)butanal

124-38-9

carbon dioxide

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

Conditions

Conditions	Yield
With ammonia under 15001.5 Torr; for 0.266667h; Pressure; Time; Concentration;	94.65%

...Expand

74-93-1

methylthiol

5809-59-6

3-cyano-3-hydroxy-1-propene

A

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

B

55064-40-9

2-[(aminocarbonyl)amino]-4-(methylthio)butanoamide

Conditions

Conditions	Yield
With ammonium carbonate In methanol at 80℃; for 1.5h;	A 85% B 12%

...Expand

17773-41-0

2-hydroxy-4-(methylthio)butyronitrile

A

89033-45-4

hydantoin amide

B

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

Conditions

Conditions	Yield
With ammonium carbonate; ammonium bicarbonate In water at 105℃; for 0.583333h; Reagent/catalyst; Autoclave;	A 17.9% B 74.9%

Reaxys ID: 12045731

Reaxys ID: 12045731

A

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

B

59-51-8

DL-methionine

C

19298-72-7

DL-methionine amide

Conditions

Conditions	Yield
Stage #1: With carbon dioxide In water at 60℃; under 112511 Torr; Stage #2: With ammonia In water at 250℃; Stage #3: titanium(IV) oxide at 180℃;	A n/a B 63% C n/a

...Expand

59-51-8

DL-methionine

sodium cyanate

sodium cyanate

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

Conditions

Conditions	Yield
With hydrogenchloride

17773-41-0

2-hydroxy-4-(methylthio)butyronitrile

506-87-6

ammonium carbonate

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

74-90-8

hydrogen cyanide

3268-49-3

3-(methylsulfenyl)propanal

124-38-9

carbon dioxide

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

Conditions

Conditions	Yield
With ammonia; water at 105 - 130℃; Industrial scale;

...Expand

74-90-8

hydrogen cyanide

3268-49-3

3-(methylsulfenyl)propanal

506-87-6

ammonium carbonate

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

Conditions

Conditions	Yield
In water at 110℃; for 1h;

...Expand

74-93-1

methylthiol

74-90-8

hydrogen cyanide

124-38-9

carbon dioxide

107-02-8

acrolein

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

Conditions

Conditions	Yield
With ammonia In methanol at 80℃; for 1.5h;

...Expand

potassium cyanide

3268-49-3

3-(methylsulfenyl)propanal

ammonium bicarbonate

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

Conditions

Conditions	Yield
at 60 - 140℃; for 0.116667h; Temperature;

...Expand

17773-41-0

2-hydroxy-4-(methylthio)butyronitrile

124-38-9

carbon dioxide

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

Conditions

Conditions	Yield
With ammonia; ammonium bicarbonate In water at 80 - 130℃; Temperature; Large scale;

methionine aldehyde

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 20 °C / 760.05 Torr 2: water / 2.5 h / 75 °C / 760.05 Torr View Scheme

506-87-6

ammonium carbonate

methionine cyanohydrin

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

Conditions

Conditions	Yield
In water at 75℃; under 760.051 Torr; for 2.5h;

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

59-51-8

DL-methionine

Conditions

Conditions	Yield
Stage #1: 5-[2-(methylthio)ethyl]imidazolidine-2,4-dione With water; potassium carbonate at 120 - 160℃; Sonication; Stage #2: at 80 - 120℃; Reagent/catalyst; Sonication;	99.9%
Stage #1: 5-[2-(methylthio)ethyl]imidazolidine-2,4-dione With water; potassium hydroxide at 173 - 178℃; for 1h; Stage #2: With carbon dioxide; water at 20℃; Crystallization; Presence of polyvinyl alcohol;	97%
With water; potassium hydroxide at 120 - 173℃; pH=10.5;	53.6%

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

A

63-68-3

L-methionine

B

54896-74-1

(S)-N-carbamoylmethionine

Conditions

Conditions	Yield
In water at 30℃; for 72h; Mechanism; Pseudomonas sp. strain NS671, air. pH 7.0 - 7.2; different cultivation times, other 5-substituted hydantoins;	A 98% B n/a
With sodium hydroxide; air at 30℃; for 72h; Pseudomonas sp. Strain NS671;	A 93% B n/a
at 40℃; Product distribution; Mechanism; conversion by Pseudomonas sp. strain NS671;

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

23479-37-0

(R)-N-carbamoylmethionine

Conditions

Conditions	Yield
With D-hydantoinase 1 In water at 50℃; for 12.7h; pH 8.5;	81%
With Tris-HCl buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; Mechanism; pH 8.5; enzymatic reaction;
With Tris-HCl buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h;

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

10049-07-7

rhodium(III)chloride

Rh(3+)*H(1+)*CH3SCH2CH2C3HN2O2(2-)*2Cl(1-)*H2O = Rh(C6H9N2O2S)Cl2(H2O)

Conditions

Conditions	Yield
With water In not given heating (pH=3); filtration, washing (H2O and EtOH), further product on evapn. of filtrate, addn. of Na2CO3 (pH = 3), drying; elem. anal.;	42%

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

74-88-4

methyl iodide

7673-71-4

[2-(2,5-dioxo-imidazolidin-4-yl)-ethyl]-dimethyl sulfonium ; iodide

Conditions

Conditions	Yield
With water

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

348-67-4

D-methionine

Conditions

Conditions	Yield
Mechanism; enzymatic hydrolysis of several hydantoines with Pseudomonas Sp.;
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; pH 8.0; enzymatic reaction;
at 37℃; Pseudomonas Sp.;
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h;

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

63-68-3

L-methionine

Conditions

Conditions	Yield
at 30℃; Product distribution; conversion by E. coli pHPB12;
at 30℃; Arthrobacter globiformis;
Multi-step reaction with 3 steps 1.1: sodium hydroxide; pyrographite / 130 °C 2.1: 5 h / pH 2 - 4 2.2: 65 °C / pH 4 3.1: sodium hydroxide; cobalt(II) chloride / 36 h / 37 °C / pH 6.5 / Large scale; Enzymatic reaction View Scheme

13253-44-6

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

22818-40-2

D-4-hydroxyphenylglycine

Conditions

Conditions	Yield
In water at 30℃; for 24h; Product distribution; 0.1 M potassium phosphate buffer (pH = 8.0); bacterioal strain H-319; also H-968;

5-(2-Methylthioethyl)hydantoin Chemical Properties

5-(2-Methylthioethyl)hydantoin Toxicity Data With Reference

5-(2-Methylthioethyl)hydantoin Safety Profile

5-(2-Methylthioethyl)hydantoin Specification