2420-17-9

Basic information

• Product Name: 4-Hydroxyphenyl hydantoin
• Synonyms: 5-(4-HYDROXYPHENYL)2,4-IMIDAZOLIDINEDIONE;5-(4-HYDROXYPHENYL)HYDANTOIN;4-HYDROXYPHENYL HYDANTOIN;5-(P-HYDROXYPHENYL)HYDANTOIN;RARECHEM AP KH 0026;5-(4-Hydroxyphenyl)2,4-Imidazolidinedine;Hydroxyphenylhydantoin;5-(4-hydroxyphenyl)imidazolidine-2,4-dione
• CAS NO: 2420-17-9
• Molecular Formula: C₉H₈N₂O₃
• Molecular Weight: 192.17
• EINECS: 219-340-8
• Mol File: 2420-17-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: >260°C
• Boiling Point: 273.7℃[at 101 325 Pa]
• Appearance: white powder
• Density: 1.408
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.607
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 8.67±0.10(Predicted)
• Water Solubility: 1.29g/L at 20℃
• CAS DataBase Reference: 4-Hydroxyphenyl hydantoin(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxyphenyl hydantoin(2420-17-9)
• EPA Substance Registry System: 4-Hydroxyphenyl hydantoin(2420-17-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• Hazardous Substances Data: 2420-17-9(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C9H8N2O3/c12-6-3-1-5(2-4-6)7-8(13)11-9(14)10-7/h1-4,7,12H,(H2,10,11,13,14)

Upstream product

• 97-59-6 Allantoin 
• 108-95-2 phenol 
• 1198-84-1 4-hydroxymandelic acid 
• 57-13-6 urea 
• 298-12-4 Glyoxilic acid 
• 461-72-3 2,4-imidazolidinedione 
• 29410-13-7 5-hydroxy-hydantoin 
• 32282-43-2 DL-5-chlorohydantoin 
• 173904-10-4 5-bromohydantoin 
• 143-33-9 sodium cyanide 
• 506-87-6 ammonium carbonate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 151-50-8 potassium cyanide 

Downstream Products

• 6324-01-2 p-hydroxyphenylglycine 
• 22818-40-2 D-4-hydroxyphenylglycine 
• 68780-35-8 N-carbamyl-D-p-hydroxyphenylglycine 

Relevant articles and documents

Preparation method of p-hydroxyphenylhydantoin

The invention provides a preparation method of p-hydroxyphenylhydantoin. The p-hydroxyphenylhydantoin is obtained by a condensing cyclization reaction of glyoxylic acid, phenol and urea, which are used as raw materials, under the catalysis of a solid acid, and the solid acid is at least one of an acidic ion exchange resin, a heteropoly acid, a metal salt, a carrier-supported metal salt compound and a metal oxide. The preparation method which adopts the solid acid as a catalyst has the characteristics of simple process, high product selectivity, few byproducts, high yield, good purity, and easiness in product separation, and is suitable for large-scale industrial production.

Production method for para hydroxybenzene

The invention provides a production method for para hydroxybenzene and belongs to the field of chemical engineering and pharmaceutical production. Glyoxylic acid is added dropwise to urea, phenol and a hydrochloric acid system to synthesize crude para hydroxybenzene, and fine para hydroxybenzene is prepared through a refining procedure. According to the production method for para hydroxybenzene, a proper raw material ratio, proper reaction temperature and other synthesis conditions are selected, the refining procedure is added, therefore, the yield of para hydroxybenzene can be effectively increased, and the yield of para hydroxybenzene can reach 70% or above; the technological process is simple, easy to carry out and free of pollution.

The use of Lewis acids in the synthesis of 5-arylhydantoins

Different Lewis acids are able to promote the Friedel-Crafts reaction between 5-bromohydantoin and aromatic compounds. In the case of phenol, mixtures of ortho and para isomers are always obtained, with Mg(ClO4) 2 leading to the best selectivity. However, the best overall yield of 5-(hydroxyphenyl)hydantoin is obtained with YbCl3. This method can be extended to other aromatic systems such as anisole and thiophene. These reactions give similar yields but proceed with total selectivity to 5-(4-methoxyphenyl)hydantoin and 5-(2-thiophenyl)hydantoin, respectively. The cationic exchange of MgII and YbIII on anionic solid supports allows the preparation of very efficient heterogeneous catalysts for this reaction (productivity up to 600 mol of hydantoin per mole of Mg). These catalysts have practical advantages in that they can be recycled and reused.