16935-34-5

Basic information

• Product Name: 5-Isopropylhydantoin
• Synonyms: 5-isopropylhydantoin;5-(1-Methylethyl)-2,4-imidazolidinedione;5-Isopropyl-2,4-imidazolidinedione;5-LSOPROPYLHYDANTOIN;4-Isopropylhydantoin;5-Isopropylhydantoin 5-(1-Methylethyl)-2,4-imidazolidinedione
• CAS NO: 16935-34-5
• Molecular Formula: C₆H₁₀N₂O₂
• Molecular Weight: 142.16
• EINECS: 1312995-182-4
• Mol File: 16935-34-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 144-145 °C(Solv: water (7732-18-5))
• Appearance: /
• Density: 1.129 g/cm³
• Refractive Index: 1.462
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 8.85±0.10(Predicted)
• CAS DataBase Reference: 5-Isopropylhydantoin(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Isopropylhydantoin(16935-34-5)
• EPA Substance Registry System: 5-Isopropylhydantoin(16935-34-5)

Safety Data

• Hazardous Substances Data: 16935-34-5(Hazardous Substances Data)

Usage

General Description

5-Isopropylhydantoin is a chemical compound with the formula C7H12N2O2. It is a white crystalline solid with a faint odor, and it is used in various industries including pharmaceuticals, agriculture, and cosmetics. 5-Isopropylhydantoin is commonly used as a raw material in the synthesis of other chemicals and pharmaceuticals, and it is also utilized as an intermediate in the production of pesticides and herbicides. Additionally, it has applications in the production of personal care products and cosmetics. 5-Isopropylhydantoin is known for its ability to act as a reactive intermediate in organic synthesis and for its potential as an antiepileptic agent. Due to its wide range of uses, 5-Isopropylhydantoin is an important and versatile chemical in the industrial sector.

InChI:InChI=1/C6H10N2O2/c1-3(2)4-5(9)8-6(10)7-4/h3-4H,1-2H3,(H2,7,8,9,10)

Upstream product

• 26081-02-7 (S)-N-carbamoyl-valine 
• 516-06-3 D,L-valine 
• 1207610-49-8 carbamoyl-valine methylamide 
• 91121-79-8 5-isopropylidene-2-thioxo-imidazolidin-4-one 
• 151-50-8 potassium cyanide 
• 78-84-2 isobutyraldehyde 
• 81965-27-7 N-(2-chloroethyl)-N-nitrosocarbamoyl valinamide 
• 108-91-8 cyclohexylamine 
• 506-87-6 ammonium carbonate 
• 60586-49-4 2-amino-3,3-dimethylpropionitrile hydrochloride 
• 26081-00-5 N-carbamoyl-valine 
• 7526-77-4 5-iso-propylidenehydantoin 

Downstream Products

• 640-68-6 D-Val-OH 
• 72-18-4 L-valine 
• 26081-02-7 (S)-N-carbamoyl-valine 
• 1045819-83-7 C₁₇H₂₄N₂O₂ 
• 71921-91-0 3-methyl-5-isopropylhydantoin 

Relevant articles and documents

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A new general pathway for synthesis of reference compounds of N-terminal valine-isocyanate adducts

Adducts to Hb could be used as biomarkers to monitor exposure to isocyanates. Particularly useful is the measurement of carbamoylation of N-terminal valines in Hb, after detachment as hydantoins. The synthesis of references from the reactive isocyanates, especially diisocyanates, has been problematic due to side reactions and polymerization of the isocyanate starting material. A simpler, safer, and more general method for the synthesis of valine adducts of isocyanates has been developed using N-[(4-nitrophenyl)-carbamate] valine methylamide (NPCVMA) as the key precursor to adducts of various mono-and diisocyanates of interest. By reacting NPCVMA with a range of isocyanate-related amines, carbamoylated valines are formed without the use of the reactive isocyanates. The carbamoylated products synthesized here were cyclized with good yields of the formed hydantoins. The carbamoylated derivative from phenyl isocyanate also showed quantitative yield in a test with cyclization under the conditions used in blood. This new pathway for the preparation of N-carbamoylated model compounds overcomes the abovementioned problems in the synthesis and is a general and simplified approach, which could make such reference compounds of adducts to N-terminal valine from isocyanates accessible for biomonitoring purposes. The synthesized hydantoins corresponding to adducts from isocyanic acid, methyl isocyanate, phenyl isocyanate, and 2,6-toluene diisocyanate were characterized by LC-MS analysis. The background level of the hydantoin from isocyanic acid in human blood was analyzed with the LC-MS conditions developed.

Decomposition of N-(2-chloroethyl)-N-nitrosocarbamoyl amino acid amides

The chemical decomposition of N-(2-chloroethyl)-N-nitrosocarbamoyl (Q(NO)) prolinamide and valinamide were studied under physiological conditions. The volatile products were identified with GC. Q(NO)-Pro-NH2 gave twice the amount of ethylene glycol and only one-fifth of the 2-chloroethanol produced by Q(NO)-Val-NH2 or BCNU, pointing to different pathways of their decomposition. The carbamoylating activity was also investigated in the presence of cyclohexylamine, and it was found to lead mainly to intramolecular carbamoylation with the formation of hydantoin derivatives.