33599-32-5

Basic information

• Product Name: 1-N-BUTYLHYDANTOIN
• Synonyms: 1-N-BUTYL-2,4-DIOXOIMIDAZOLIDINE;1-N-BUTYLHYDANTOIN;1-butylimidazolidine-2,4-dione;1-Butylhydantoin;1-N-BUTYLHYDANTOIN 98+%;1-Butyl-2,4-dioxoimidazolidine;2,4-IMidazolidinedione, 1-butyl-;1-Butyl-2,4-imidazolidinedione
• CAS NO: 33599-32-5
• Molecular Formula: C₇H₁₂N₂O₂
• Molecular Weight: 156.18
• EINECS: 251-585-6
• Mol File: 33599-32-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 94°C
• Appearance: /
• Density: 1.12 g/cm³
• Refractive Index: 1.48
• CAS DataBase Reference: 1-N-BUTYLHYDANTOIN(CAS DataBase Reference)
• NIST Chemistry Reference: 1-N-BUTYLHYDANTOIN(33599-32-5)
• EPA Substance Registry System: 1-N-BUTYLHYDANTOIN(33599-32-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37/39-36/37
• Hazardous Substances Data: 33599-32-5(Hazardous Substances Data)

Usage

General Description

1-N-butylhydantoin, also known as N-butyl-1H-imidazolidine-2,4-dione, is a chemical compound used in various industrial and pharmaceutical applications. It is a derivative of hydantoin, a heterocyclic organic compound, and is classified as an anticonvulsant drug. 1-N-butylhydantoin is known for its ability to prevent seizures by inhibiting excessive electrical activity in the brain. It is also used as a corrosion inhibitor in metalworking fluids and as an intermediate in the synthesis of other chemicals. 1-N-BUTYLHYDANTOIN is considered to have low toxicity and is generally regarded as safe for use in these applications.

InChI:InChI=1/C7H12N2O2/c1-2-3-4-9-5-6(10)8-7(9)11/h2-5H2,1H3,(H,8,10,11)

Upstream product

• 104892-32-2 1-carbethoxymethyl-1-(n-butyl)urea 
• 590-28-3 potassium cyanate 
• 3182-83-0 ethyl 2-(n-butyl)aminoacetate 
• 131543-46-9 Glyoxal 
• 592-31-4 1-butyl-urea 
• 461-72-3 2,4-imidazolidinedione 
• 542-69-8 1-iodo-butane 

Downstream Products

• 171515-72-3 1-Butyl-5-[1-{2-butyl-3-[4-(2-trityl-2H-tetrazol-5-yl)-benzyl]-3H-imidazol-4-yl}-meth-(Z)-ylidene]-imidazolidine-2,4-dione 
• 171515-73-4 1-Butyl-5-[1-{2-butyl-3-[4-(2-trityl-2H-tetrazol-5-yl)-benzyl]-3H-imidazol-4-yl}-meth-(E)-ylidene]-imidazolidine-2,4-dione 
• 160998-29-8 methyl (E)-4-<<2-butyl-5-<(3-butyl-2,5-dioxo-4-imidazolidinylidene)methyl>-1H-imidazol-1-yl>methyl>benzoate 
• 152147-95-0 methyl Z-4'-[[2-butyl-5-[(3-butyl-2,5-dioxo-4-imidazolidinylidene)methyl]-1H-imidazol-1-yl]methyl][1,1'-biphenyl]-2-carboxylate 
• 1187307-84-1 (Z)-5-(4-chlorobenzylidene)-1-n-butylhydantoin 
• 1187307-83-0 (E)-5-(4-chlorobenzylidene)-1-n-butylhydantoin 
• 1187307-82-9 (Z)-5-benzylidene-1-n-butylhydantoin 
• 1187307-81-8 (E)-5-benzylidene-1-n-butylhydantoin 
• 1344708-84-4 3-benzyl-1-butylimidazolidine-2,4-dione 

Relevant articles and documents

5-Benzylidene-hydantoins: Synthesis and antiproliferative activity on A549 lung cancer cell line

Benzylidene hydantoins have been recently reported as a new class of EGFR inhibitors. We describe here a simple and efficient methodology for the parallel solution-phase synthesis of a library of 5-benzylidene hydantoins, which were evaluated for antiproliferative activity on the human lung adenocarcinoma A549 cell line. Various substituents at positions 1, 3 and 5 on the hydantoin nucleus were examined. In the presence of a 5-benzylidene group and of a lipophilic substituent at position 1, most of the tested compounds inhibited cell proliferation at a concentration of 20 μM. Compound 7 (UPR1024), bearing 1-phenethyl and (E)-5-p-OH-benzylidene substituents, was found to be the most active derivative of the series. It inhibited EGFR autophosphorylation and induced DNA damage in A549 cells. Compound 7 and other synthesized 5-benzylidene hydantoin derivatives increased p53 levels, suggesting that the dual mechanism of action was a common feature shared by compound 7 and other member of the series.

Synthesis of new chiral mono-, di-, tri-, and tetraalkylglycolurils

Two general procedures were developed for the synthesis of chiral N-mono-, N, N′-di-, N, N′ N″-tri-, and N, N′, N″, N′″-tetraalkylglycolurils based on the reactions of 4,5-dihydroxy-imidazolidin-2-ones or glyoxal with one or two moles of alkylureas, respectively, by acid catalysis. The reactions of N-monoalkyl- and N, N′-dialkylureas with glyoxal proceed regioselectively. The mechanism of these reactions was suggested and partly confirmed by quantum-chemical calculations and experimental data. The enantiomeric separation of some chiral glycolurils by chiral-phase HPLC was carried out for the first time.

Process for producing 1-substituted-hydantoins

The subject is to provides a process for producing 1-substituted-hydantoins of Formula I: wherein R1represents a hydrocarbon group which may be substituted and others,characterized by reacting N-substituted-N-alkoxycarbonylamino-acetonitrile of Formula II: wherein R2represents an alkyl group and others,with an alkali metal hydroxides or the like and then treating with an acid.