2,6-Dimethylbenzoquinone
[CAS# 527-61-7]

Identification

• Name: 2,6-Dimethylbenzoquinone
• Synonyms: 2,6-Dimethyl-p-benzoquinone); 2,6-Dimethyl-1,4-benzoquinone; 2,6-Dimethyl-2,5-cyclohexadiene-1,4-dione; 3,5-Dimethylbenzoquinone; m-Xyloquinone
• Molecular Formula: C₈H₈O₂
• Molecular Weight: 136.15
• CAS Registry Number: 527-61-7
• EC Number: 208-420-8
• SMILES: CC1=CC(=O)C=C(C1=O)C

Properties

• Density: 1.115
• Melting point: 71-73 ºC
• Boiling point: 201 ºC
• Refractive index: 1.
• Flash point: 71 ºC

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H315-H318-H319-H332-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318

Discovory and Applicatios

2,6-Dimethylbenzoquinone is an important organic compound that belongs to the class of quinones, characterized by its distinct aromatic structure and unique reactivity. This compound is derived from the oxidation of 2,6-dimethylphenol, which itself is a product of toluene and other precursors. The discovery of 2,6-dimethylbenzoquinone occurred in the early 20th century as chemists explored the properties and reactivity of quinonoid compounds. The synthesis of this compound is typically achieved through the oxidation of 2,6-dimethylphenol using various oxidizing agents, including potassium permanganate or chromium trioxide, under controlled conditions.

The structural configuration of 2,6-dimethylbenzoquinone includes two methyl groups on the benzene ring at the 2 and 6 positions and two carbonyl groups that contribute to its reactivity and chemical behavior. This compound exhibits significant biological and chemical properties, making it a valuable intermediate in various applications.

One of the primary applications of 2,6-dimethylbenzoquinone lies in organic synthesis, where it serves as a versatile building block for the synthesis of more complex organic molecules. Its reactivity allows it to participate in electrophilic addition reactions, enabling the formation of various derivatives. These derivatives are often utilized in the pharmaceutical industry to develop new drugs and therapeutic agents.

In addition to its role in organic synthesis, 2,6-dimethylbenzoquinone is also employed as a reagent in analytical chemistry. Its unique properties make it suitable for the detection of certain functional groups in organic compounds, facilitating the identification and characterization of various substances. The compound’s ability to undergo redox reactions is particularly useful in electrochemical studies and applications.

Another notable application of 2,6-dimethylbenzoquinone is in the field of material science. Its reactivity and ability to form stable adducts with other compounds allow it to be incorporated into polymer matrices. This incorporation can enhance the mechanical properties and thermal stability of polymers, leading to the development of advanced materials with tailored characteristics for specific applications, such as coatings and adhesives.

In the biological realm, 2,6-dimethylbenzoquinone has garnered interest for its potential role in biological systems. Research indicates that it may possess antioxidant properties, which could make it beneficial in various applications, including cosmetics and food preservation. The compound's ability to scavenge free radicals could help protect against oxidative stress, which is associated with various diseases and aging processes.

Safety considerations are paramount when handling 2,6-dimethylbenzoquinone, as it can be irritating to the skin and respiratory system. Appropriate safety measures, including the use of personal protective equipment and proper ventilation, should be implemented to minimize exposure during synthesis and application.

In conclusion, 2,6-dimethylbenzoquinone is a versatile compound with significant implications in organic synthesis, analytical chemistry, material science, and potential biological applications. Its discovery has paved the way for advancements in various fields, showcasing the importance of quinonoid compounds in modern chemistry and industry. Ongoing research into its properties and applications continues to expand its utility, highlighting its relevance in contemporary scientific endeavors.

References

2021. 2,6-Dimethylbenzoquinone suppresses proliferation and migration of NSCLC cells via mTOR/AKT and p38 MAPK pathways. Frontiers in Pharmacology, 12.
DOI: 10.3389/fphar.2021.734485

2021. Redox-mediating 2,6-dimethylbenzoquinone for photobioelectrocatalysis. ACS Applied Materials & Interfaces, 13(38).
DOI: 10.1021/acsami.1c13901

2020. Synthesis of 1,3-benzoxathiol-2-one derivatives from 2,6-dimethylbenzoquinone. Russian Journal of Organic Chemistry, 56(12).
DOI: 10.1134/S1070428020120083