1-Acetyl-2-thiohydantoin

Base Information

• Chemical Name: 1-Acetyl-2-thiohydantoin
• CAS No.: 584-26-9
• Molecular Formula: C5H6 N2 O2 S
• Molecular Weight: 158.181
• European Community (EC) Number: 209-535-6
• NSC Number: 1920
• UNII: WMG5WO16JD
• DSSTox Substance ID: DTXSID3060401
• Nikkaji Number: J21.553H
• ChEMBL ID: CHEMBL1994284
• Mol file: 584-26-9.mol

Synonyms:1-Acetyl-2-thiohydantoin;584-26-9;4-Imidazolidinone, 1-acetyl-2-thioxo-;USAF B-7;1-acetyl-2-thioxoimidazolidin-4-one;1-acetyl-2-sulfanylideneimidazolidin-4-one;USAF BE-0405;HYDANTOIN, 1-ACETYL-2-THIO-;NSC 1920;EINECS 209-535-6;WMG5WO16JD;BRN 0127294;NSC-1920;1-ACETYL-2-THIOXO-IMIDAZOLIDIN-4-ONE;5-24-05-00242 (Beilstein Handbook Reference);NSC1920;N-acetyl-2-thiohydantoin;UNII-WMG5WO16JD;SCHEMBL1703962;CHEMBL1994284;DTXSID3060401;WLN: T5NYMV EHJ AV1 BUS;1-Acetyl-2-thioxo-4-imidazolidinone;MFCD00020879;NSC816189;STK370050;AKOS000271051;NSC-816189;1-Acetyl-2-thioxo-4-imidazolidinone #;LS-75970;NCI60_001612;4-(3,4-Dimethylphenyl)-4-oxobutyricacid;CS-0314679;FT-0632440;A831876

Chemical Property of 1-Acetyl-2-thiohydantoin

Chemical Property:

• Melting Point: 175.5°C
• Refractive Index: 1.6430 (estimate)
• PKA: 8.03±0.30(Predicted)
• PSA: 81.50000
• Density: 1.48g/cm³
• LogP: -0.48370
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 158.01499861
• Heavy Atom Count: 10
• Complexity: 214

Purity/Quality:

99.3% ^*data from raw suppliers

1-Acetyl-2-thioxoimidazolidin-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)N1CC(=O)NC1=S

Technology Process of 1-Acetyl-2-thiohydantoin

There total 7 articles about 1-Acetyl-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: 84.7%

ammonium thiocyanate (1147550-11-5) + acetic anhydride (108-24-7) + glycine (56-40-6,18875-39-3,25718-94-9) → 1-acetyl-2-thiohydantoin (584-26-9)

Guidance literature:

With acetic acid; for 2h; Microwave irradiation; Reflux;

DOI:10.1016/j.cclet.2013.05.009

Reference yield: 76.0%

thiocyanic acid (463-56-9) + acetic anhydride (108-24-7) + glycine (56-40-6,18875-39-3,25718-94-9) → 1-acetyl-2-thiohydantoin (584-26-9)

Guidance literature:

With acetic acid; at 100 ℃; for 0.666667h;

Reference yield:

ammonium thiocyanate (1147550-11-5) + glycine (56-40-6,18875-39-3,25718-94-9) → 1-acetyl-2-thiohydantoin (584-26-9)

Guidance literature:

With acetic anhydride;

upstream raw materials:

2-acetamidoacetamide

ammonium thiocyanate

acetic anhydride

glycine

Downstream raw materials:

5-benzylidene-2-thiohydantoin

(5Z)-5-(4-hydroxybenzylidene)-2-thioxoimidazolidin-4-one

5-p-methoxybenzylidene-2-thiohydantoin

(Z)-5-ethylidene-2-thioxoimidazolidin-4-one

Refernces

• 1、 Casas, Jose S.,Castineiras, Alfonso,Couce, Delfina,Playa, Nuria,Sordo, Jose,Varela, Jose M.. "1-Acetyl-2-thiohydantoin". . p. 427 - 428. Retrieved 1998.
• 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、 Tejchman, Waldemar,Orwat, Bartosz,Korona-G?owniak, Izabela,Barbasz, Anna,Kownacki, Ireneusz,Latacz, Gniewomir,Handzlik, Jadwiga,?es?awska, Ewa,Malm, Anna. "Highly efficient microwave synthesis of rhodanine and 2-thiohydantoin derivatives and determination of relationships between their chemical structures and antibacterial activity". . p. 39367 - 39380. Retrieved 2019/12/14.