1,4-NAPHTHOQUINONE

CAS no: 130-15-4

EC / List no: 204-977-6

Chemical formula: C10H6O2

Synonyms: 1,4-dihydronaphthalene-1,4-dione, 1,4-Naphthalenedione, 1,4-Naphthochinon, 1,4-NAPHTHOQUINONE, 1,4-Naphthoquinone, 1,4-naphthoquinone, 4a,8a-Dihydronaphthalene-1,4-dione, Naphthalene-1,4-dione, naphthalene-1,4-dione, naphthoquinone, NAPHTHOQUINONE-1,4

1,4-Naphthoquinone (CAS No: 130-15-4) is a yellow crystalline organic compound derived from naphthalene with the molecular formula C₁₀H₆O₂. It belongs to the naphthoquinone family, characterized by two carbonyl (quinone) groups attached to a fused aromatic ring system.

Due to its strong redox activity, electron transfer capability, and high chemical reactivity, it is widely used as an industrial intermediate, pharmaceutical precursor, and agrochemical building block.

Key Properties of 1,4-Naphthoquinone

Molar Mass: 158.15 g/mol
Appearance: Yellow to yellow-brown crystalline powder or solid
Odor: Characteristic aromatic odor
Density: ~1.32 g/cm³
Boiling Point: Decomposes before boiling under normal conditions
Melting Point: ~122–126 °C
Solubility: Slightly soluble in water; soluble in ethanol, ether, benzene, chloroform, and other organic solvents
Flash Point: ~152 °C
Vapor Pressure: Low at room temperature
Refractive Index: ~1.64
Chemical Structure: Aromatic quinone compound derived from naphthalene
Stability: Stable under recommended storage conditions; sensitive to strong oxidizing and reducing agents
Reactivity: Strong oxidizing properties and readily participates in redox reactions
Main Function: Chemical intermediate and oxidizing agent
Thermal Stability: Good thermal stability under controlled conditions

Industrial Applications

Pharmaceutical Industry

1,4-Naphthoquinone is widely used as a pharmaceutical intermediate and bioactive scaffold.

Key applications include:

Anticancer compound development
Antimicrobial and antifungal agents
Antimalarial drug synthesis
Vitamin K derivative production
Enzyme inhibition research (MAO, topoisomerase, acetyltransferase studies)

It serves as a key building block in medicinal chemistry due to its biological activity and oxidative properties.

Agrochemical Applications

1,4-Naphthoquinone is an important raw material in agrochemical synthesis, including:

Fungicides (e.g., dichlone, dithianon intermediates)
Pesticides and insecticides
Algaecides
Plant protection agents
Crop stress resistance enhancers

Its derivatives are widely used in eco-friendly crop protection formulations.

Polymer and Rubber Industry

In polymer chemistry, 1,4-naphthoquinone is used as a:

Polymerization regulator
Reaction modifier in free-radical polymerization
Stabilizer in rubber and polyester resins
Performance enhancer in elastomers

It helps control molecular weight and improves material stability.

Dye and Pigment Manufacturing

1,4-Naphthoquinone is a key intermediate in the production of:

Anthraquinone dyes
Textile pigments
Hair dye compounds (lawsone derivatives)
High fastness industrial colorants

Its quinone structure makes it highly valuable for color chemistry applications.

Chemical Synthesis & Fine Chemicals

It is widely used in organic synthesis and fine chemical manufacturing as:

Diels–Alder reaction dienophile
Intermediate for heterocyclic compounds
Precursor for aminoanthraquinones
Building block for benzofused aromatic systems

It is also used in the synthesis of functional materials and specialty molecules.

Other Industrial Applications

1,4-Naphthoquinone is used in multiple industrial sectors, including:

Chemical intermediates
Specialty chemical manufacturing
Functional material synthesis
Catalyst-related reactions
Resin and additive chemistry

It is valued for its high reactivity and electron-transfer capability.

Electronics and Advanced Materials

In advanced material science, it is explored for:

Organic semiconductors
Conductive polymer systems
Coatings with improved UV resistance
Energy-related material research

Key Functional Advantages

High chemical reactivity
Strong electron-transfer (redox) capability
Versatile intermediate for organic synthesis
Compatible with multi-step chemical processes
Valuable precursor for pharmaceuticals and dyes
Broad industrial applicability

Biological and Research Significance

1,4-Naphthoquinone is widely studied in scientific research due to its:

Antibacterial and antifungal activity
Anticancer potential
Antioxidant and pro-oxidant behavior
Role in oxidative phosphorylation and ROS generation
Enzyme inhibition properties

It is considered an important scaffold in drug discovery and bioactive molecule development.

Physical and Chemical Behavior

Slightly soluble in water
Freely soluble in organic solvents
Produces reddish-brown color in alkaline solutions
Strong reactivity in electrophilic addition reactions
Acts as a versatile quinone intermediate

1,4-Naphthoquinone is a highly versatile quinone-based chemical intermediate widely used across pharmaceutical, agrochemical, dye, polymer, and advanced material industries. Its unique redox behavior and chemical reactivity make it a key compound in both industrial production and modern research applications.