2,3,6-Trimethylphenol

• CAS: 2416-94-6
• Catalog Number: ACM2416946-1
• Category: Main Products
• Molecular Weight: 136.19
• Molecular Formula: C9H12O
• Synonyms: 3-Hydroxypseudocumene
• IUPAC Name: 2,3,6-trimethylphenol
• SMILES: CC1=C(C(=C(C=C1)C)O)C
• InChI Key: QQOMQLYQAXGHSU-UHFFFAOYSA-N
• Boiling Point: 215 °C at 760 mmHg
• Melting Point: 59-62°C
• Flash Point: 100°C
• Density: 0.996 g/cm³
• Appearance: White or yellow
• Assay: 0.9999
• Complexity: 111
• Defined Atom Stereocenter Count: 0
• EC Number: 219-330-3
• Exact Mass: 136.0888
• Formal Charge: 0
• Hazard Statements: C,Xi
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 1
• Hydrogen Bond Donor Count: 1
• Isotope Atom Count: 0
• Monoisotopic Mass: 136.0888
• Packaging: 1 kg
• Packing Group: III
• Refractive Index: 1.368 (20°C)
• Rotatable Bond Count: 0
• Safety Description: 26-39-24/25-45-36/37/39-36/37
• Storage Conditions: Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.
• Supplemental Hazard Statements: H315-H317-H318-H314
• Symbol: GHS07,GHS05
• Topological Polar Surface Area: 20.2 Ų
• WGK Germany: 1
• XLogP3-AA: 2.7

Case Study

2,3,6-Trimethylphenol in the Oxidative Synthesis of 2,3,5-Trimethyl-1,4-Benzoquinone

Wang C, et al. Catalysis Communications, 2009, 10(5), 725-727.

The catalytic oxidation of 2,3,6-trimethylphenol (TMP) to 2,3,5-trimethyl-1,4-benzoquinone has been effectively achieved using ionic liquids as co-catalysts under atmospheric oxygen. Experimental investigations employed a batch reactor system consisting of a four-neck flask equipped with a reflux condenser, gas bubbler, mechanical stirrer, and thermostatic water bath. A reaction mixture containing CuCl₂·2H₂O (0.01 mol), ionic liquid (0.01 mol), TMP (0.1 mol, 13.6 g), and n-hexanol (50 mL) was maintained at 85 °C under vigorous stirring for 5 h. Continuous oxygen supply facilitated selective oxidation, and aliquots were periodically withdrawn for GC and GC-MS analysis. Using [Bmim]BF₄ as co-catalyst, selectivity reached 96.1% with 100% conversion, highlighting the pivotal role of ionic liquid anions in controlling product yield. Furthermore, the ionic liquid phase was recoverable and reusable, underscoring its practicality in scalable synthesis of substituted benzoquinones.

2,3,6-Trimethylphenol Oxidation for the Selective Synthesis of 2,3,5-Trimethylbenzoquinone

Li Y, et al. Chemical Engineering Journal, 2009,146(2), 270-274.

The oxidation of 2,3,6-trimethylphenol (TMP) represents a highly efficient route to 2,3,5-trimethylbenzoquinone, an important intermediate in fine chemical synthesis. A Fenton-type catalytic system, employing FeSO₄·7H₂O with aqueous 5% H₂O₂, enables the transformation under mild, solvent-free conditions. In a typical experiment, TMP (1 mmol) and FeSO₄·7H₂O (5 mol%) were dissolved in deionized water (10 mL) within a three-necked flask equipped with a reflux condenser and magnetic stirrer. Hydrogen peroxide (4.1 mmol) was added dropwise at 45 °C over 3 h, affording nearly quantitative conversion with 99.9% selectivity toward the target quinone. Notably, this aqueous catalytic protocol is inexpensive, environmentally benign, and extendable to the oxidation of o-methylphenols, demonstrating broad experimental applicability in green oxidation chemistry.