2,6-Dimethylhydroquinone
[CAS# 654-42-2]

Identification

• Classification: Natural product >> Natural phenols
• Name: 2,6-Dimethylhydroquinone
• Synonyms: 1,4-Dihydroxy-2,6-dimethylbenzene
• Molecular Formula: C₈H₁₀O₂
• Molecular Weight: 138.16
• CAS Registry Number: 654-42-2
• EC Number: 211-505-2
• SMILES: CC1=CC(=CC(=C1O)C)O

Properties

• Solubility: 4.535e+004 mg/L (25 °C water)
• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.582, Calc.^*
• Melting point: 73.04 °C
• Boiling Point: 284.6±35.0 °C (760 mmHg), Calc.^*, 264.90 °C
• Flash Point: 141.1±20.5 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS08 Danger
• Risk Statements: H301-H302-H315-H318-H360
• Safety Statements: P203-P264-P264+P265-P270-P280-P301+P316-P301+P317-P302+P352-P305+P354+P338-P317-P318-P321-P330-P332+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Repr.	1B	H360

Discovery and Applications

2,6-Dimethylhydroquinone is an organic compound with significant relevance in various chemical processes and applications. This compound, classified as a dimethyl-substituted hydroquinone, features two methyl groups positioned at the 2 and 6 positions of the hydroquinone structure, resulting in unique chemical properties that enhance its utility across different industries.

The discovery of 2,6-dimethylhydroquinone dates back to ongoing research in the field of organic chemistry, specifically within the study of phenolic compounds. Hydroquinones are known for their ability to act as reducing agents and antioxidants due to their structural characteristics, which allow them to undergo reversible oxidation and reduction reactions. The introduction of methyl groups at specific positions further modulates the compound's reactivity, stability, and solubility, making 2,6-dimethylhydroquinone a valuable compound in synthetic chemistry.

One of the primary applications of 2,6-dimethylhydroquinone is as an intermediate in the synthesis of various organic compounds. Its unique reactivity enables its use in the production of specialty chemicals, including dyes, fragrances, and pharmaceuticals. In particular, 2,6-dimethylhydroquinone has been employed in the synthesis of polymer additives, enhancing the properties of plastics and coatings.

In addition to its role as a synthetic intermediate, 2,6-dimethylhydroquinone is recognized for its antioxidant properties. This makes it useful in formulations aimed at preventing oxidative degradation in materials and products. The compound effectively scavenges free radicals, which can lead to the deterioration of sensitive substances, thereby extending the shelf life and stability of various formulations, including cosmetics, food products, and industrial materials.

The pharmaceutical industry also leverages the properties of 2,6-dimethylhydroquinone, particularly in the development of antioxidant formulations. By incorporating this compound into drug formulations, manufacturers can enhance the stability of active pharmaceutical ingredients (APIs), preventing degradation during storage and ensuring therapeutic effectiveness.

Furthermore, 2,6-dimethylhydroquinone has been studied for its potential applications in the field of green chemistry. Researchers have explored its use in environmentally friendly processes, including its role as a reagent in catalytic reactions that aim to minimize waste and reduce the environmental impact of chemical manufacturing.

Despite its numerous advantages, the safety profile and environmental impact of 2,6-dimethylhydroquinone warrant consideration. As with many organic compounds, it is essential to assess its potential toxicity and biodegradability to ensure responsible use in various applications. Ongoing research aims to establish comprehensive safety data and guidelines for its application across different industries.

In summary, 2,6-dimethylhydroquinone is a versatile compound with significant applications in the synthesis of organic chemicals, as well as its role as an antioxidant in various formulations. Its discovery and subsequent applications highlight the importance of phenolic compounds in advancing chemical processes and product development.

References

2018. Radiation-thermal decomposition of lignin: Products and the mechanism of their formation (Review). High Energy Chemistry, 52(1).
DOI: 10.1134/s0018143918010095

2007. A Practical Synthesis of the Ansa Chain of Benzenic Ansamycin Antibiotics: Total Synthesis of an Ansatrienol Derivative. Synthesis, 2007(3).
DOI: 10.1055/s-2006-958967