CAS No.77-71-4,2,4-Imidazolidinedione,5,5-dimethyl- Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	77-71-4
Name:	2,4-Imidazolidinedione,5,5-dimethyl-
Article Data:	51
Cas Database

Formula:	C₅H₈N₂O₂
Molecular Weight:	128.131
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;
EINECS:	201-051-3
Density:	1.142 g/cm³
Melting Point:	174-177 °C(lit.)
Boiling Point:	237.54°C (rough estimate)
Flash Point:	193oC
Solubility:	soluble in water
Appearance:	white to off-white crystals or crystalline powder
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	22-24/25-36/37-26
Transport Information:	N/A
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

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Consensus Reports

Reported in EPA TSCA Inventory.

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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