Hydantoin

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Hydantoin

Hydantoin (pronounced: hi-dan-toe-in) is a heterocyclic organic compound that is a type of imidazolidine. It is a white crystalline solid that is slightly soluble in water and polar organic solvents.

Etymology

The term "hydantoin" is derived from the Greek words "hydor" meaning water and "antos" meaning flower. This is in reference to the compound's formation from water and urea.

Structure and Properties

Hydantoin is a five-membered ring compound, with two nitrogen atoms at positions 1 and 3, and a carbonyl group at positions 2 and 4. It is a tautomeric compound, meaning it can exist in two structural forms that are in equilibrium with each other.

Synthesis

Hydantoin can be synthesized from glycolic acid and ammonia under heat and pressure. This reaction is known as the Bucherer-Bergs reaction.

Uses

Hydantoin and its derivatives are used in a variety of applications. They are used in the synthesis of anticonvulsants, such as phenytoin and ethotoin. They are also used as plasticizers and as additives in cosmetics, due to their moisturizing properties.

Related Terms

  • Imidazolidine: A type of heterocyclic compound that is structurally similar to hydantoin.
  • Bucherer-Bergs reaction: A chemical reaction used to synthesize hydantoin.
  • Phenytoin: An anticonvulsant drug that is a derivative of hydantoin.
  • Ethotoin: Another anticonvulsant drug that is a derivative of hydantoin.

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