2-Thiohydantoin

Base Information

• Chemical Name: 2-Thiohydantoin
• CAS No.: 503-87-7
• Molecular Formula: C3H4 N2 O S
• Molecular Weight: 116.144
• Hs Code.: 2933990090
• European Community (EC) Number: 207-977-4
• NSC Number: 11772
• UNII: CP2PH1A61R
• DSSTox Substance ID: DTXSID2060121
• Nikkaji Number: J9.400E
• ChEMBL ID: CHEMBL1958109
• Mol file: 503-87-7.mol

Synonyms:Thiohydantoin;Thiohydantoins

Chemical Property of 2-Thiohydantoin

Chemical Property:

• Appearance/Colour: BROWN CRYSTALLINE POWDER
• Melting Point: 229-231 ºC
• Refractive Index: 1.6550 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: 8.50±0.10(Predicted)
• Flash Point: °C
• PSA: 73.22000
• Density: 1.49g/cm³
• LogP: -0.35170
• Storage Temp.: Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 116.00443393
• Heavy Atom Count: 7
• Complexity: 122

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Thiohydantoin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=O)NC(=S)N1
• Uses: Reactant for synthesis of:? ;Drugs with antidiabetic activity1? ;Barbituric acid and thiohydantoin derivatives with antimicrobial activity2? ;Possible anticancer agents3? ;Fibroblast growth factor receptor 1 kinase inhibitors4? ;HIV-1 integrase inhibitors5Reactant for persilylation6 2-Thiohydantoin is a useful synthetic intermediate. It is a reactant for synthesis of drugs with antidiabetic activity, barbituric acid and thiohydantoin derivatives with antimicrobial activity, and possible anticancer agents. Reactant for synthesis of:Drugs with antidiabetic activityBarbituric acid and thiohydantoin derivatives with antimicrobial activityPossible anticancer agentsFibroblast growth factor receptor 1 kinase inhibitorsHIV-1 integrase inhibitorsReactant for persilylation

Technology Process of 2-Thiohydantoin

There total 39 articles about 2-Thiohydantoin 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: 98.0%

1-acetyl-2-thiohydantoin (584-26-9) → 2-thiohydantoin (503-87-7)

Guidance literature:

With sodium methylate; In methanol; at 0 - 20 ℃; pH=10; Inert atmosphere; Molecular sieve;

DOI:10.1055/s-0030-1260259

Reference yield: 91.0%

thiourea (17356-08-0) + glycine (56-40-6,18875-39-3,25718-94-9) → 2-thiohydantoin (503-87-7)

Guidance literature:

for 0.5h; Heating;

DOI:10.3390/11100739

Reference yield: 61.0%

Glyoxal (131543-46-9,107-22-2) + thiourea (17356-08-0) → 2-thiohydantoin (503-87-7)

Guidance literature:

Glyoxal; With phosphorus pentoxide; water; at 20 ℃; for 0.0833333h;

thiourea; at 20 ℃; for 0.166667h;

DOI:10.1016/j.tetlet.2011.02.002

upstream raw materials:

N-(acetyl-thiocarbamoyl)-glycine

N-(5-amino-thiazol-2-yl)-benzamide

N-[(benzoylamino)thioxomethyl]glycine

N-(o-carboxybenzoyl)glycine

Downstream raw materials:

5-benzylidene-2-thiohydantoin

(5Z)-5-((1H-indol-3-yl)methylene)-2-thioxoimidazolidin-4-one

5-Piperonyliden-2-thiohydantoin

5-(3-methyl-cyclohexyLiDene)-2-thioxo-imidazolidin-4-one

Refernces

• 1、 Johnson. "-". . p. 780. Retrieved 1913.
• 2、 Bispo, Marcelle de Lima Ferreira,Garbin, Renata Perugini Biasi,Macedo, Fernando,Nakazato, Gerson,Ogatta, Sueli Fumie Yamada,Ribeiro, Jhonatan Macedo,de Carvalho, Priscila Goes Camargo,de Fátima, ?ngelo. "Synthesis and antimicrobial activity of thiohydantoins obtained from L-amino acids". . p. 94 - 102. Retrieved 2020/02/06.
• 3、 -. "A heterocyclic compound and use thereof". Paragraph 0117; 0121-0123. . Retrieved 2017/11/16.