PRODUCTS

2-IMIDAZOLIDINE-DIONE

2-imidazolidine-dione is used component in cosmetic formulations.
2-imidazolidine-dione is used stabilizing agent in polymer industries.
2-imidazolidine-dione is primarily used for its reactivity in forming derivatives for medical and industrial applications.

CAS Number: 461-72-3
EC Number: 207-317-3
Molecular Formula: C6H14N4O

SYNONYMS:
Hydantoin, 2,4-Imidazolidinedione, Imidazolidin-2,4-dione, Hydantoin, Glycolylurea, Glycolurea, Imidazolidinedione, 2,4-Imidazolidinedione, 2-Oxoimidazolidine, Imidazole-2,4-dione, Ureidoacetic acid, 2,4-Imidazolidinedione, Glycolylurea, Imidazole-2,4(3H,5H)-dione, 2,4(3H,5H)-Imidazoledione, 2-Imidazolin-4(or 5)-one, 2-hydroxy-, HYDANTOIN, imidazolidine-2,4-dione, 461-72-3, 2,4-Imidazolidinedione, Glycolylurea, Imidazole-2,4(3H,5H)-dione, MFCD00005259, 2,4(3H,5H)-Imidazoledione, 2-Imidazolin-4(or 5)-one, 2-hydroxy-, CHEBI:27612, NSC-9226, I6208298TA, Hydantoins, HYDANTOINE, CCRIS 6532, NSC 9226, EINECS 207-313-3, EPA Pesticide Chemical Code 128826, BRN 0110598, 2,4-(3H,5H)-imidazoledione, UNII-I6208298TA, Hydantoin, 98%, 2,4-imidazolinedione, 2,5H)-Imidazoledione, imidazolidine-2,4dione, HYDANTOIN [MI], Imidazole-2,5H)-dione, HYDANTOIN [WHO-DD], SCHEMBL27690, 5-24-05-00188 (Beilstein Handbook Reference), MLS001074863, SCHEMBL9391323, DTXSID1052111, NSC9226, HMS2234P13, HMS3373G13, BBL013200, BDBM50549804, STL164008, AKOS000119723, CS-W011328, NCGC00246990-01, AS-10977, NCI60_042041, SMR000568395, H0167, NS00019989, EN300-18068, C05146, D70295, Q418082, Q-201207, Z57131035, F0001-1249, InChI=1/C3H4N2O2/c6-2-1-4-3(7)5-2/h1H2,(H2,4,5,6,7)

2-imidazolidine-dione is an imidazolidine-2,4-dione.
2-imidazolidine-dione, commonly referred to as Hydantoin, has the molecular formula C₃H₄N₂O₂ and a molecular weight of 100.08 g/mol.
2-imidazolidine-dione is a heterocyclic compound widely used in various applications, including as an intermediate in pharmaceutical synthesis, cosmetics, and materials science.

2-imidazolidine-dione, commonly referred to as hydantoin, is an organic compound characterized by a five-membered heterocyclic ring structure with two nitrogen atoms and a ketone group.
2-imidazolidine-dione can be synthesized through various methods, including condensation reactions involving urea and glyoxylic acid or similar reagents.

2-imidazolidine-dione is a heterocyclic organic compound with the formula CH2C(O)NHC(O)NH.
2-imidazolidine-dione is a colorless solid that arises from the reaction of glycolic acid and urea.
2-imidazolidine-dione is an oxidized derivative of imidazolidine.

In a more general sense, 2-imidazolidine-dione can refer to groups or a class of compounds with the same ring structure as the parent compound.
For example, phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a 2-imidazolidine-dione molecule.

USES and APPLICATIONS of 2-IMIDAZOLIDINE-DIONE:
Pharmaceuticals uses of 2-imidazolidine-dione: Hydantoin derivatives are used as anticonvulsants (e.g., phenytoin), targeting sodium channels to stabilize neuronal membranes.
Industrial Uses of 2-imidazolidine-dione: Employed as intermediates in organic synthesis and components of resins and polymers.

Cosmetics uses of 2-imidazolidine-dione: Found in preservatives like diazolidinyl urea due to its antimicrobial properties.
2-imidazolidine-dione is use dintermediate in the synthesis of pharmaceuticals.
2-imidazolidine-dione is used precursor in the manufacture of agrochemicals.

2-imidazolidine-dione is used component in cosmetic formulations.
2-imidazolidine-dione is used stabilizing agent in polymer industries.

2-imidazolidine-dione is primarily used for its reactivity in forming derivatives for medical and industrial applications.
2-imidazolidine-dione and its derivatives serve as intermediates in the synthesis of pharmaceuticals and other chemicals.

PROPERTIES AND USES OF 2-IMIDAZOLIDINE-DIONE:
*Chemical Structure:
Cyclic urea derivative with a saturated C₃N₂ ring and a ketone functional group.

*Physical Properties:
Typically a white crystalline solid, soluble in water and polar solvents.

BENEFITS OF 2-IMIDAZOLIDINE-DIONE:
*High thermal stability.
*Biodegradable and environmentally friendly.
*Versatility in various chemical synthesis pathways.

USES AND OCCURRENCE OF 2-IMIDAZOLIDINE-DIONE:
*Pharmaceuticals
The 2-imidazolidine-dione group can be found in several medicinally important compounds.
In pharmaceuticals, 2-imidazolidine-dione derivatives form a class of anticonvulsants; phenytoin and fosphenytoin both contain 2-imidazolidine-dione moieties and are both used as anticonvulsants in the treatment of seizure disorders.

The 2-imidazolidine-dione derivative dantrolene is used as a muscle relaxant to treat malignant hyperthermia, neuroleptic malignant syndrome, spasticity, and ecstasy intoxication.
Ropitoin is an example of an antiarrhythmic 2-imidazolidine-dione.

*Pesticides
The 2-imidazolidine-dione derivative Imiprothrin is a pyrethroid insecticide. Iprodione is a popular fungicide containing the 2-imidazolidine-dione group.

SYNTHESIS OF AMINO ACIDS:
Hydrolysis of 2-imidazolidine-dione afford amino acids:
RCHC(O)NHC(O)NH+H2O⟶RCHC(NH2)COOH+NH3
2-imidazolidine-dione itself reacts with hot, dilute hydrochloric acid to give glycine. Methionine is produced industrially via the hydantoin obtained from methional.

*Methylation
Methylation of 2-imidazolidine-dione yields a variety of derivatives.
Dimethylhydantoin (DMH) [10] may refer to any dimethyl derivative of 2-imidazolidine-dione, but especially 5,5-dimethylhydantoin.

*Halogenation
Some N-halogenated derivatives of 2-imidazolidine-dione are used as chlorinating or brominating agents in disinfectant/sanitizer or biocide products.
The three major N-halogenated derivatives are dichlorodimethylhydantoin (DCDMH), bromochlorodimethylhydantoin (BCDMH), and dibromodimethylhydantoin (DBDMH).
A mixed ethyl-methyl analogue, 1,3-dichloro-5-ethyl-5-methylimidazolidine-2,4-dione (bromochloroethylmethylhydantoin), is also used in mixtures with the above.

*DNA oxidation to 2-imidazolidine-dione after cell death
A high proportion of cytosine and thymine bases in DNA are oxidized to 2-imidazolidine-dione over time after the death of an organism.
Such modifications block DNA polymerases and thus prevents PCR from working.
Such damage is a problem when dealing with ancient DNA samples.

SYNTHESIS OF 2-IMIDAZOLIDINE-DIONE:
2-imidazolidine-dione was first isolated in 1861 by Adolf von Baeyer in the course of his study of uric acid.
He obtained 2-imidazolidine-dione by hydrogenation of allantoin, hence the name.
Friedrich Urech synthesized 5-methylhydantoin in 1873 from alanine sulfate and potassium cyanate in what is now known as the Urech 2-imidazolidine-dione synthesis.

The method is very similar to the modern route using alkyl and arylcyanates.
The 5,5-dimethyl compound can also be obtained from acetone cyanohydrin (also discovered by Urech: see cyanohydrin reaction) and ammonium carbonate.
This reaction type is called the Bucherer–Bergs reaction.

2-imidazolidine-dione can also be synthesized either by heating allantoin with hydroiodic acid or by "heating bromacetyl urea with alcoholic ammonia".
The cyclic structure of 2-imidazolidine-dione was confirmed by Dorothy Hahn 1913.
Of practical importance, 2-imidazolidine-dione is obtained by condensation of a cyanohydrin with ammonium carbonate.
Another useful route, which follows the work of Urech, involves the condensation of amino acids with cyanates and isocyanates:

PHYSICAL and CHEMICAL PROPERTIES of 2-IMIDAZOLIDINE-DIONE:
Appearance: White crystalline powder,
Melting Point: 218-220 °C (lit.),
Solubility: Slightly soluble in water,
Molecular Formula: C3H4N2O2,
Molecular Weight: 100.08 g/mol,
Appearance: White crystalline solid,
Melting Point: 221–226 °C,
Boiling Point: Decomposes before boiling,
Solubility: Soluble in water, ethanol; slightly soluble in ether and chloroform,
Density: 1.56 g/cm³,
Molecular Weight: 100.08 g/mol,

XLogP3: -1.7,
Hydrogen Bond Donor Count: 2,
Hydrogen Bond Acceptor Count: 2,
Rotatable Bond Count: 0,
Exact Mass: 100.027277375 g/mol,
Monoisotopic Mass: 100.027277375 g/mol,
Topological Polar Surface Area: 58.2Å²,
Heavy Atom Count: 7,
Formal Charge: 0,

Complexity: 120,
Isotope Atom Count: 0,
Defined Atom Stereocenter Count: 0,
Undefined Atom Stereocenter Count: 0,
Defined Bond Stereocenter Count: 0,
Undefined Bond Stereocenter Count: 0,
Covalently-Bonded Unit Count: 1,
Compound Is Canonicalized: Yes

FIRST AID MEASURES of 2-IMIDAZOLIDINE-DIONE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of 2-IMIDAZOLIDINE-DIONE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.

FIRE FIGHTING MEASURES of 2-IMIDAZOLIDINE-DIONE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of 2-IMIDAZOLIDINE-DIONE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of 2-IMIDAZOLIDINE-DIONE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.

STABILITY and REACTIVITY of 2-IMIDAZOLIDINE-DIONE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature) .
-Possibility of hazardous reactions:
No data available