1,4-naphthoquinone

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  1. 1,4-Naphthoquinone

1,4-Naphthoquinone, also known as para-naphthoquinone, is an organic compound with the formula C₁₀H₆O₂. It is a yellow crystalline solid that is soluble in organic solvents. This compound is a derivative of naphthalene, featuring a quinone functional group. It is an important intermediate in the synthesis of various dyes, pharmaceuticals, and agrochemicals.

Structure and Properties[edit | edit source]

1,4-Naphthoquinone is characterized by a bicyclic structure consisting of a naphthalene ring system with two ketone groups at the 1 and 4 positions. This arrangement gives it a planar structure and contributes to its reactivity as a quinone.

  • **Molecular Formula:** C₁₀H₆O₂
  • **Molar Mass:** 158.15 g/mol
  • **Appearance:** Yellow crystalline solid
  • **Melting Point:** 125-127 °C
  • **Boiling Point:** 295 °C

Synthesis[edit | edit source]

1,4-Naphthoquinone can be synthesized through the oxidation of naphthalene or 1,4-dihydroxynaphthalene. Common oxidizing agents used in these reactions include chromic acid and potassium permanganate.

Applications[edit | edit source]

1,4-Naphthoquinone is used in the production of dyes, such as vat dyes and anthraquinone dyes. It is also a precursor in the synthesis of vitamin K and other biologically active compounds. In addition, it serves as a building block in the synthesis of various pharmaceuticals and agrochemicals.

Biological Activity[edit | edit source]

1,4-Naphthoquinone and its derivatives exhibit a range of biological activities, including antibacterial, antifungal, and anticancer properties. These activities are often attributed to their ability to undergo redox cycling and generate reactive oxygen species, which can damage cellular components.

Safety and Handling[edit | edit source]

1,4-Naphthoquinone is a hazardous substance and should be handled with care. It can cause skin and eye irritation, and prolonged exposure may lead to more serious health effects. Appropriate personal protective equipment, such as gloves and goggles, should be used when handling this compound.

Also see[edit | edit source]

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