1-(Hydroxymethyl)-5,5-dimethylhydantoin

Base Information

• Chemical Name: 1-(Hydroxymethyl)-5,5-dimethylhydantoin
• CAS No.: 116-25-6
• Molecular Formula: C6H10N2O3
• Molecular Weight: 158.157
• Hs Code.: 2933.21
• European Community (EC) Number: 204-132-1
• NSC Number: 9185
• UNII: 5CW1VP51HL
• DSSTox Substance ID: DTXSID6035152
• Nikkaji Number: J5.277I
• Wikidata: Q27261848
• Metabolomics Workbench ID: 45029
• ChEMBL ID: CHEMBL1892087
• Mol file: 116-25-6.mol

Synonyms:1-monomethylol-5,5-dimethylhydantoin;cpd with unspecified hydroxymethyl locants of 1-monomethylol-5,5-dimethylhydantoin;methyloldimethylhydantoin

Chemical Property of 1-(Hydroxymethyl)-5,5-dimethylhydantoin

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Melting Point: 104-106 °C
• Refractive Index: 1.493
• PKA: 8.28±0.10(Predicted)
• PSA: 69.64000
• Density: 1.257 g/cm³
• LogP: -0.46670
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Sensitive.: Moisture Sensitive
• Solubility.: DMSO (Heated), Methanol (Slightly)
• Water Solubility.: Freely soluble in water.
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 158.06914219
• Heavy Atom Count: 11
• Complexity: 212

Purity/Quality:

98% min ^*data from raw suppliers

1-(Hydroxymethyl)-5,5-dimethylhydantoin >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36:Wear suitable prot

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(=O)NC(=O)N1CO)C
• Uses: 1-Hydroxymethyl-5,5-dimethylhydantoin is used as chelator for light-sensitive pharmaceutical drug, and as raw material of water-soluble polymers. It also can be used as a soluble inhibitor for proteins. It is used as an adjuvant in the bleaching of food-contact recycled paper and board used in food packaging.

Technology Process of 1-(Hydroxymethyl)-5,5-dimethylhydantoin

There total 1 articles about 1-(Hydroxymethyl)-5,5-dimethylhydantoin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → 1-(hydroxymethyl)-5,5-dimethyl hydantoin (116-25-6)

Guidance literature:

Reference yield:

1-(hydroxymethyl)-5,5-dimethyl hydantoin (116-25-6) → 2-benzyl-2,3,3a,9-tetrahydro-3,3-dimethylimidazo[5,1-b][2,3]benzothiazin-1-one

Guidance literature:

Multi-step reaction with 5 steps

1.1: 100 percent / SOCl₂ / CH₂Cl₂ / 12 h / 20 °C

2.1: NaOMe / dimethylformamide / 1 h / 20 °C

2.2: 79 percent / dimethylformamide / 20 °C

3.1: 93 percent / sodium borohydride / ethanol / 20 °C

4.1: 92 percent / TFA / 24 h / 20 °C

5.1: NaH / tetrahydrofuran / 0.58 h / 20 °C

5.2: 58 percent / tetrahydrofuran / 60 h / 20 °C

With sodium tetrahydroborate; thionyl chloride; sodium methylate; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b508214e

Reference yield:

1-(hydroxymethyl)-5,5-dimethyl hydantoin (116-25-6) → 1-(o-bromophenyl)thiomethyl-5,5-dimethylhydantoin (873193-00-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 100 percent / SOCl₂ / CH₂Cl₂ / 12 h / 20 °C

2.1: NaOMe / dimethylformamide / 1 h / 20 °C

2.2: 71 percent / dimethylformamide / 20 °C

With thionyl chloride; sodium methylate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b508214e

upstream raw materials:

formaldehyd

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

Downstream raw materials:

4-hydroxy-5,5-dimethyl-1-phenylthiomethylimidazolidin-2-one

5,5-dimethyl-1-phenylthiomethylhydantoin

3,5,5-trimethyl-1-phenylthiomethylhydantoin

4-hydroxy-3,5,5-trimethyl-1-phenylthiomethylimidazolidin-2-one