2,4,6-Trihydroxytoluene

• CAS: 88-03-9
• Catalog Number: ACM88039
• Category: Main Products
• Molecular Weight: 140.14
• Molecular Formula: C₇H₈O₃
• Synonyms: 2.4.6-Trioxy-1-methyl-benzol; 2.4.6-Trihydroxy-toluol; 2-Methylphloroglucinol; 2,6-Trihydroxytoluene; C-Methylphloroglucin; 2-methylbenzene-1,3,5-triol; Phloroglucinol,methyl; 1,3,5-Benzenetriol,2-methyl; 2,4,6-Trihydroxytoluene; Toluene-2,6-triol; Methylphloroglucinol; 2-Methyl-phloroglucin
• IUPAC Name: 2-methylbenzene-1,3,5-triol
• SMILES: CC1=C(C=C(C=C1O)O)O
• InChI Key: BPHYZRNTQNPLFI-UHFFFAOYSA-N
• Boiling Point: 313.1ºC at 760 mmHg
• Flash Point: 160.6ºC
• Density: 1.387g/cm³
• Appearance: Solid
• EC Number: 201-792-2
• Exact Mass: 140.04700

Case Study

2,4,6-Trihydroxytoluene as a Regioselective Precursor for 7-Methylaurone Synthesis

Shubin, Dmitry A., et al. Chemistry of Heterocyclic Compounds 55.12 (2019): 1174-1178.

2,4,6-Trihydroxytoluene (2-methylphloroglucinol, MPG) serves as a readily accessible starting material for the first scalable synthesis of (Z)-4,6-dihydroxy-7-methylaurones, including a synthetic analog of natural 7-methylaureusidin, reducing reliance on plant extraction from Cyperus capitatus.
Synthetic Protocol: MPG undergoes regioselective acylation with chloroacetonitrile catalyzed by anhydrous ZnCl2 and HCl in diethyl ether (0 °C to room temperature), forming a ketimine intermediate (83% yield) that hydrolyzes to 4,6-dihydroxy-7-methylbenzofuran-3(2H)-one (78% yield). Base-catalyzed condensation with substituted benzaldehydes yields the target aurones.
Performance Evaluation: The route exhibits excellent regiocontrol, with DFT calculations confirming a favorable 22.1 kcal/mol activation barrier for the preferred cyclization pathway. Condensation reactions proceed in 61-89% yield, and all products form the thermodynamically stable Z-isomer verified by NMR. This method enables efficient, cost-effective access to biologically relevant aurone derivatives for antitumor and anti-infective screening.

2,4,6-Trihydroxytoluene as a Versatile Precursor for Nitrosoazo Dyes on Polycaproamide Fibers

Kobrakov, K. I., et al. Fibre Chemistry 48.6 (2017): 462-465.

2,4,6-Trihydroxytoluene (methylphloroglucinol, MPG) serves as an accessible, cost-effective precursor derived from recycled TNT, enabling the synthesis of novel nitrosoazo disperse dyes for polycaproamide (Capron) fabrics with high color fastness and fungicidal activity.
Synthetic Protocol: MPG is first converted into monoazo intermediates, which then undergo regioselective nitrosation with NaNO2 and 50% H2SO4 at -10 to 5 °C. The reaction affords nitrosoazo dyes in 75-88% yield. Structures are confirmed by ¹H NMR, IR spectroscopy, and elemental analysis.
Performance Evaluation: The dyes deliver uniform yellow-to-red-brown shades on polycaproamide via disperse dyeing. Color fastness reaches grades 4-5 against dry/wet friction, laundering, and perspiration. Several derivatives show strong fungicidal activity against Aspergillus niger, Penicillium chrysogenum, and Chaetomium globosum. Nitroso substitution further enhances antifungal effects. This approach valorizes waste TNT into high-performance textile dyes, supporting domestic production and import substitution.

Custom Q&A

What is the molecular formula of 2,4,6-Trihydroxytoluene?

The molecular formula of 2,4,6-Trihydroxytoluene is C7H8O3.

What are the synonyms of 2,4,6-Trihydroxytoluene?

The synonyms of 2,4,6-Trihydroxytoluene include 2-methylbenzene-1,3,5-triol, 2-Methylphloroglucinol, Toluene-2,4,6-triol, and more.

What are some identifiers for 2,4,6-Trihydroxytoluene?

Some identifiers for 2,4,6-Trihydroxytoluene include CAS number 88-03-9, EC number 201-792-2, and NSC number 112934.

What is the IUPAC name of 2,4,6-Trihydroxytoluene?

The IUPAC name of 2,4,6-Trihydroxytoluene is 2-methylbenzene-1,3,5-triol.

What is the InChI of 2,4,6-Trihydroxytoluene?

The InChI of 2,4,6-Trihydroxytoluene is InChI=1S/C7H8O3/c1-4-6(9)2-5(8)3-7(4)10/h2-3,8-10H,1H3.

What is the molecular weight of 2,4,6-Trihydroxytoluene?

The molecular weight of 2,4,6-Trihydroxytoluene is 140.14g/mol.

How many hydrogen bond donor counts are there in 2,4,6-Trihydroxytoluene?

There are 3 hydrogen bond donor counts in 2,4,6-Trihydroxytoluene.

How many hydrogen bond acceptor counts are there in 2,4,6-Trihydroxytoluene?

There are 3 hydrogen bond acceptor counts in 2,4,6-Trihydroxytoluene.

How many rotatable bond counts are there in 2,4,6-Trihydroxytoluene?

There are 0 rotatable bond counts in 2,4,6-Trihydroxytoluene.

What is the topological polar surface area of 2,4,6-Trihydroxytoluene?

The topological polar surface area of 2,4,6-Trihydroxytoluene is 60.7Ų.