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

Description

5-Isopropylhydantoin, with the chemical formula C7H12N2O2, is a white crystalline solid characterized by a faint odor. It is a versatile chemical compound that serves as a crucial intermediate in various industrial applications, including pharmaceuticals, agriculture, and cosmetics, due to its unique properties as a reactive intermediate in organic synthesis and its potential as an antiepileptic agent.

Uses

Used in Pharmaceutical Industry:
5-Isopropylhydantoin is used as a raw material for the synthesis of other chemicals and pharmaceuticals, playing a vital role in the development of new medications and therapeutic agents.
Used in Agricultural Industry:
5-Isopropylhydantoin is utilized as an intermediate in the production of pesticides and herbicides, contributing to the development of effective and environmentally friendly solutions for crop protection.
Used in Cosmetics Industry:
5-Isopropylhydantoin is employed in the production of personal care products and cosmetics, where it serves as a key component in the formulation of various products, enhancing their efficacy and performance.
Used in Organic Synthesis:
5-Isopropylhydantoin is used as a reactive intermediate in organic synthesis, enabling the creation of a wide range of chemical compounds for diverse applications across different industries.
Used in Antiepileptic Research:
5-Isopropylhydantoin is explored for its potential as an antiepileptic agent, offering new avenues for the development of treatments for epilepsy and other neurological disorders.

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

• 26081-00-5 N-carbamoyl-valine 
• 516-06-3 D,L-valine 
• 1207610-49-8 carbamoyl-valine methylamide 
• 26081-02-7 (S)-N-carbamoyl-valine 
• 91121-79-8 5-isopropylidene-2-thioxo-imidazolidin-4-one 
• 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 
• 7526-77-4 5-iso-propylidenehydantoin 
• 151-50-8 potassium cyanide 
• 78-84-2 isobutyraldehyde 

Downstream Products

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

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.