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5,5-Dimethylhydantoin

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Name

5,5-Dimethylhydantoin

EINECS 201-051-3
CAS No. 77-71-4 Density 1.142 g/cm3
PSA 58.20000 LogP 0.26200
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 N/A Appearance white to off-white crystals or crystalline powder
Safety 22-24/25-36/37-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 77-71-4 (5,5-Dimethylhydantoin) Hazard Symbols IrritantXi
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;

Article Data 51

5,5-Dimethylhydantoin 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
ConditionsYield
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
ConditionsYield
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;
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
ConditionsYield
With potassium cyanide In ethanol; water at 50℃; for 72h;A 77.8%
B 2%
C 7.3%
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
ConditionsYield
hydrolysis; Yield given;A 62.5%
B n/a
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
ConditionsYield
With potassium cyanide In ethanol; water at 50℃; for 24h;A 62.5%
B 15%
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
ConditionsYield
With potassium cyanide In ethanol; water at 50℃; for 24h;A 62.5%
B n/a
463-79-6

carbonic-acid

19355-69-2

2-amino-2-cyanopropane

77-71-4

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

Conditions
ConditionsYield
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
ConditionsYield
With potassium cyanide In ethanol; water at 50℃; for 24h;A 45%
B 2%
C 15.7%
D 23%
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
ConditionsYield
With sulfuric acid In water at 0℃; for 0.0833333h;A 21%
B 33%
5392-23-4

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

77-71-4

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

Conditions
ConditionsYield
With potassium permanganate; water

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.

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