Dimethadione

Base Information

• Chemical Name: Dimethadione
• CAS No.: 695-53-4
• Deprecated CAS: 60254-97-9
• Molecular Formula: C5H7NO3
• Molecular Weight: 129.115
• Hs Code.: 29349990
• European Community (EC) Number: 211-781-4
• NSC Number: 756741,30152
• UNII: ALU9NPM703
• DSSTox Substance ID: DTXSID2020478
• Nikkaji Number: J6.938H
• Wikidata: Q27166437
• NCI Thesaurus Code: C171703
• ChEMBL ID: CHEMBL1099
• Mol file: 695-53-4.mol

Synonyms:5,5-Dimethyl-2,4-oxazolidinedione;5,5-Dimethyloxazolidine-2,4-dione;Dimethadione;Dimethyloxazolidinedione

Chemical Property of Dimethadione

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 4.01mmHg at 25°C
• Melting Point: 77-80 °C(lit.)
• Refractive Index: 1.464
• Boiling Point: 137 °C / 6mmHg
• PKA: 6.13(at 37℃)
• Flash Point: 44.2oC
• PSA: 55.40000
• Density: 1.204 g/cm³
• LogP: 0.36020
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 129.042593085
• Heavy Atom Count: 9
• Complexity: 173

Purity/Quality:

99.0% ^*data from raw suppliers

5,5-Dimethyloxazolidinedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-40-33-36/37/38
• Safety Statements: 22-36-24/25-23-36/37-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(=O)NC(=O)O1)C
• Uses: Reactant involved in:? ;Synthesis of nickel benzoannulated or naphthoannulated β-oxatetraazachlorin complex1? ;Being used as a cathepsin K inhibitor2Molecule involved in pharmacological studies including:? ;Identification of bioequivalent generic substitute for antiepileptic drugs3? ;Screening for drugs that shift energy metabolism from mitochondrial respiration to glycolysis4? ;Dissolving protein plugs in patients with choledochal cyst / pancreaticobiliary maljunctions5 anticonvulsant 5,5-Dimethyloxazolidine-2,4-dione is in vivo measurement of intracellular pH.

Technology Process of Dimethadione

There total 16 articles about Dimethadione 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: 72.0%

ethyl 2-hydroxy-2,2-dimethylethanoate (80-55-7) + Trichloroacetyl isocyanate (3019-71-4) → dimethadione (695-53-4)

Guidance literature:

ethyl 2-hydroxy-2,2-dimethylethanoate; Trichloroacetyl isocyanate; In dichloromethane; at 0 - 20 ℃;

With triethylamine; In ethanol; Reflux;

DOI:10.1016/j.tetlet.2008.11.124

Reference yield:

urea (57-13-6) + ethyl 2-hydroxy-2,2-dimethylethanoate (80-55-7) → dimethadione (695-53-4)

Guidance literature:

With sodium ethanolate;

DOI:10.1021/ja01854a019

Reference yield:

5,5-dimethyl-4-p-tolylimino-oxazolidin-2-one (26212-62-4) → dimethadione (695-53-4)

Guidance literature:

With hydrogenchloride; In ethanol; for 10h; Heating;

DOI:10.1021/jo00837a011

upstream raw materials:

5,5-dimethyl-2-thioxo-4-oxazolidinone

diethyl sulphite

sodium ethanolate

urea

Downstream raw materials:

trimethadione

3-ethyl-5,5-dimethyl-oxazolidine-2,4-dione

3-Benzoyl-5,5-dimethyl-oxazolidine-2,4-dione

5,5-dimethyl-N-[(4-methylphenyl)sulfonyl]oxazolidine-2,4-dione

Refernces

• 1、 Santana, Ana Bela,Lucas, Susana D.,Goncalves, Lidia M.,Correia, Henrique F.,Cardote, Teresa A.F.,Guedes, Rita C.,Iley, Jim,Moreira, Rui. "N-Acyl and N-sulfonyloxazolidine-2,4-diones are pseudo-irreversible inhibitors of serine proteases". scheme or table. p. 3993 - 3997. Retrieved 2012/07/03.
• 2、 -. "Process for producing 2,4-oxazolidinedione". . . Retrieved 2008/06/13.