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2-Methylhydroquinone
[CAS# 95-71-6]

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Identification
ClassificationPharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Fluoropyridine
Name2-Methylhydroquinone
Synonyms2,5-Dihydroxytoluene; 2-Methyl-1,4-benzenediol; Toluhydroquinone; THQ
Molecular StructureCAS # 95-71-6, 2-Methylhydroquinone
Molecular FormulaC7H8O2
Molecular Weight124.14
CAS Registry Number95-71-6 (96937-50-7)
EC Number202-443-7
SMILESCC1=C(C=CC(=C1)O)O
Properties
Water solubility77 g/L (25 °C)
Density1.2±0.1 g/cm3, Calc.*
Melting point125-128 °C
Index of Refraction1.595, Calc.*
Boiling Point277.8±20.0 °C (760 mmHg), Calc.*, 285 °C
Flash Point140.2±16.4 °C, Calc.*, 172 °C
*Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbolssymbol symbol symbol symbol   GHS05;GHS07;GHS08;GHS09 Danger  Details
Risk StatementsH302-H315-H317-H318-H319-H335-H341-H351-H400-H410  Details
Safety StatementsP203-P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P318-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Acute toxicityAcute Tox.4H302
Acute hazardous to the aquatic environmentAquatic Acute1H400
Skin irritationSkin Irrit.2H315
Germ cell mutagenicityMuta.2H341
CarcinogenicityCarc.2H351
Serious eye damageEye Dam.1H318
Eye irritationEye Irrit.2H319
Skin sensitizationSkin Sens.1H317
Specific target organ toxicity - single exposureSTOT SE3H335
Chronic hazardous to the aquatic environmentAquatic Chronic1H410
Skin corrosionSkin Corr.1AH314
Acute toxicityAcute Tox.4H312
Acute toxicityAcute Tox.3H301
Acute toxicityAcute Tox.4H332
SDSAvailable
up Discovery and Applications
2-Methylhydroquinone, also known as 2-methyl-1,4-benzenediol, is an organic compound characterized by a benzene ring with two hydroxyl groups (-OH) positioned at the 1 and 4 carbon atoms, with a methyl group (-CH3) at the 2 position. This compound is a structural isomer of hydroquinone and has gained interest in various chemical applications since its discovery in the early 20th century. The synthesis of 2-methylhydroquinone can be achieved through several methods, including the reduction of 2-methylbenzoquinone or through the catalytic hydrogenation of ortho- or para-nitrotoluene.

The primary application of 2-methylhydroquinone is as an antioxidant in various industrial processes. Its chemical structure allows it to act as a radical scavenger, effectively preventing oxidative degradation in products such as plastics, rubber, and cosmetics. This property is particularly important in preserving the stability and shelf life of these materials, ensuring their performance and safety in consumer products.

In addition to its role as an antioxidant, 2-methylhydroquinone serves as a precursor in the synthesis of various pharmaceuticals and fine chemicals. Its ability to undergo further chemical transformations allows for the development of compounds with diverse biological activities. For instance, derivatives of 2-methylhydroquinone have been explored for their potential anti-inflammatory and antimicrobial properties, making them candidates for drug development in the pharmaceutical industry.

Moreover, 2-methylhydroquinone is utilized in the synthesis of dyes and pigments. Its structure provides a basis for creating colored compounds, which are valuable in the textile and paint industries. The compound's reactivity facilitates the formation of azo dyes and other colorants, contributing to its significance in these applications.

Despite its beneficial uses, 2-methylhydroquinone poses safety considerations that must be addressed. Like many phenolic compounds, it can be irritating to the skin and eyes and may have toxic effects if ingested or inhaled. Regulatory agencies have established guidelines for its safe handling in industrial processes to minimize health risks. Proper safety measures, such as personal protective equipment and adequate ventilation, are essential when working with this compound.

Recent research has also begun to focus on the environmental impact of 2-methylhydroquinone and its derivatives. Efforts are being made to explore greener synthesis methods and alternative compounds that can provide similar functions while reducing environmental harm. This shift towards sustainability reflects a broader commitment within the chemical industry to address ecological concerns.

In conclusion, 2-methylhydroquinone is an important compound with significant applications in antioxidant production, pharmaceuticals, and dye synthesis. Its discovery has contributed to advancements in these fields, though safety and environmental considerations must remain a priority. Ongoing research aims to enhance its applications while promoting sustainable practices in its use.

References

2023. Potential of the enzyme laccase for the synthesis and derivatization of antimicrobial compounds. World Journal of Microbiology and Biotechnology, 39(3).
DOI: 10.1007/s11274-023-03539-x

2024. Holographic Polymer Nanocomposites with High Refractive Index Modulation by Doping Liquid Crystal E6M. Chinese Journal of Polymer Science, 42(4).
DOI: 10.1007/s10118-024-3110-z

2023. Proliferation Inhibitory Activity of Quinones from Blaps rynchopetera Defense Secretion on Colorectal Tumor Cells. Chinese Journal of Integrative Medicine, 29(4).
DOI: 10.1007/s11655-023-3696-y
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