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2,4-Dihydroxybenzenes

2,4-Dihydroxybenzenes

£70.10

2,4-Dihydroxybenzenes, also known as hydroquinone derivatives, are a class of organic compounds that have garnered significant attention in recent years due to their diverse range of applications in various fields. These compounds, characterized by the presence of two hydroxyl groups attached to a benzene ring at positions 2 and 4, exhibit unique chemical and biological properties that make them valuable in industries such as pharmaceuticals, cosmetics, and agriculture. One of the most notable applications of 2,4-dihydroxybenzenes is in the synthesis of antioxidants, which are essential in preventing oxidative stress and cell damage in living organisms. The hydroxyl groups in these compounds enable them to scavenge free radicals, thereby protecting cells from damage caused by reactive oxygen species. This property has led to the development of various antioxidant-based products, including skincare creams, nutritional supplements, and food preservatives. In addition to their antioxidant properties, 2,4-dihydroxybenzenes have also been found to exhibit antimicrobial and anti-inflammatory activities, making them promising candidates for the development of novel therapeutic agents. For instance, certain derivatives of hydroquinone have been shown to inhibit the growth of bacteria and fungi, highlighting their potential as natural preservatives in food and pharmaceutical applications. Furthermore, 2,4-dihydroxybenzenes have been explored as intermediates in the synthesis of various bioactive compounds, including flavonoids, phenolic acids, and lignins. These compounds are known to play crucial roles in plant defense mechanisms, and their biosynthesis is often regulated by environmental factors such as light, temperature, and soil quality. In conclusion, 2,4-dihydroxybenzenes are a fascinating class of compounds that have far-reaching implications in various fields. Their unique chemical and biological properties make them valuable in the development of novel products and therapeutic agents, and continued research into their applications is likely to uncover even more exciting opportunities in the years to come.

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Okay, I can write an article based on “2,4-Dihydroxybenzenes.” Since the prompt is very broad, I’ll focus on the common forms of 2,4-dihydroxybenzene, primarily resorcinol, and cover its properties, uses, and some related compounds. Here’s the article:

2,4-Dihydroxybenzene: Resorcinol and its Significance

2,4-Dihydroxybenzene, also known as resorcinol, is an aromatic organic compound with the formula C6H4(OH)2. It’s one of three isomeric benzenediols (the others being catechol and hydroquinone), distinguished by the placement of the two hydroxyl (-OH) groups on the benzene ring. Resorcinol and its derivatives find applications in a diverse range of industries, owing to its reactivity and unique chemical properties.

Properties of Resorcinol

Resorcinol is a white, crystalline solid at room temperature. It has a characteristic mild phenolic odor. Key properties include:

  • Solubility: Soluble in water, alcohol, and ether. Aqueous solutions are weakly acidic.
  • Melting Point: Approximately 110-112°C.
  • Reactivity: Undergoes typical reactions of phenols, including electrophilic aromatic substitution. It is more reactive than phenol itself due to the activating effect of the two hydroxyl groups.
  • Tautomerism: Exists in equilibrium with its keto tautomers, although the dihydroxy form is strongly favored.
  • Reducing Agent: Resorcinol can act as a reducing agent.
  • Complex Formation: Forms complexes with certain metal ions.

Production

Historically, resorcinol was produced via the alkali fusion of certain resins or via the reduction of m-dinitrobenzene. Modern industrial production typically involves the sulfonation of benzene, followed by alkali fusion of the resulting benzene-m-disulfonic acid. Newer methods are also being explored, focusing on more sustainable and efficient processes.

Uses and Applications

Resorcinol’s versatility stems from its ability to participate in various chemical reactions. Some prominent applications include:

  • Resins and Polymers: A crucial ingredient in the production of resorcinol-formaldehyde resins, used as adhesives, particularly in the wood industry (e.g., for plywood and laminated beams). These resins offer good bonding strength and water resistance. They are also used in tire manufacturing to bond rubber to textile cords.
  • Dyes and Pigments: A precursor in the synthesis of many dyes and pigments, especially those used in textile dyeing.
  • Pharmaceuticals: Resorcinol has antiseptic, disinfectant, and keratolytic properties. It is used topically in creams and lotions to treat skin conditions like acne, eczema, and psoriasis. However, due to potential skin irritation, its concentration in such preparations is carefully controlled.
  • Cosmetics: Used in some cosmetic formulations, such as hair dyes and certain skin care products, often as an antiseptic or exfoliant. Its use in cosmetics is increasingly regulated due to potential health concerns at higher concentrations.
  • Chemical Intermediate: A key intermediate in the synthesis of various other organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals.
  • UV Absorbers: Derivatives of resorcinol are used as UV absorbers in plastics and coatings to protect them from degradation caused by sunlight.
  • Photography: Previously used in photographic developers.

Derivatives and Related Compounds

Several important compounds are derived from resorcinol:

  • Resorcinol-Formaldehyde Resins: As mentioned above, these are a widely used class of thermosetting polymers.
  • 4-Hexylresorcinol: An antiseptic and anesthetic with applications in throat lozenges and skin creams.
  • Orcinol: 5-Methylresorcinol, found in lichens and used as a reagent in chemical analysis.
  • Phloroglucinol: 1,3,5-Trihydroxybenzene, a related compound with various applications in pharmaceuticals and explosives.

Safety and Handling

Resorcinol can be irritating to the skin, eyes, and respiratory system. Prolonged or repeated exposure can cause dermatitis. It should be handled with appropriate personal protective equipment (PPE), such as gloves, goggles, and a respirator if necessary. Consult safety data sheets (SDS) for detailed handling and safety information.

Conclusion

2,4-Dihydroxybenzene, primarily in the form of resorcinol, is a versatile aromatic compound with a broad spectrum of applications. From adhesives and dyes to pharmaceuticals and cosmetics, its reactivity and unique properties make it a valuable chemical building block in numerous industries. While its benefits are significant, responsible handling and awareness of potential health concerns are crucial for its safe and effective use. Ongoing research focuses on developing more sustainable production methods and exploring new applications for resorcinol and its derivatives.

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