5307-05-1

Usage

Uses

Used in Flavoring Industry:
4-Methoxy-2-methylphenol is used as a flavoring agent for its distinct aromatic properties, particularly in the production of vanilla and coffee flavors, enhancing the sensory experience of these products.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 4-Methoxy-2-methylphenol serves as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new medications.
Used in Dye and Fragrance Production:
4-Methoxy-2-methylphenol is utilized as a key component in the production of dyes and fragrances, leveraging its aromatic characteristics to create a variety of scent profiles and colorants.
Used in Medical Treatments:
4-Methoxy-2-methylphenol has been investigated for its potential use in the treatment of respiratory diseases such as tuberculosis, capitalizing on its antiseptic and expectorant properties to aid in therapeutic applications.

Upstream product

• 95-71-6 2-methylbenzene-1,4-diol 
• 124-41-4 sodium methylate 
• 23562-77-8 2-(dimethylaminomethyl)-4-methoxyphenol 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 533-18-6 2-methylphenyl acetate 
• 95-48-7 ortho-cresol 
• 24599-58-4 2,5-dimethoxy toluene 
• 7664-93-9 sulfuric acid 
• 23438-23-5 4-hydroxy-4-methyl-cyclohexa-2,5-dienone 
• 578-58-5 2-methylmethoxybenzene 
• 127136-79-2 2-Methoxymethoxy-5-methoxytoluene 
• 611-22-3 N-(o-tolyl)hydroxylamine 
• 208399-66-0 4-methoxy-2-methylphenyl boronic acid 

Downstream Products

• 103168-03-2 1-(2-hydroxy-5-methoxy-3-methyl-phenyl)-hexadecan-1-one 
• 64997-56-4 (2'E)-1-hydroxy-2-(3',7'-dimethylocta-2',6'-dienyl)-4-methoxy-6-methylbenzene 
• 13522-81-1 4-methoxy-2-methylphenyl acetate 
• 51906-20-8 (E,E,E)-2-geranylgeranyl-4-methoxy-6-methylphenol 
• 936247-40-4 C₁₁H₁₀BrNO₂S 
• 493-35-6 (2RS,4'R,8'R)-5,7-Dimethyl-tocol 
• 5548-30-1 2,5-dimethoxy-3-methylbenzaldehyde 
• 5600-82-8 2,5-dimethoxy-3-methylphenylmethanol 
• 39064-88-5 3-Methyl-4-phenoxy-phenol 
• 82721-06-0 5-methoxy-2-phenoxy-toluene 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 95-71-6 2-methylbenzene-1,4-diol 
• 936247-46-0 C₁₄H₁₆BrNO₂S 

Relevant academic research and scientific papers

Enantioselective Cleavage of Cyclobutanols Through Ir-Catalyzed C?C Bond Activation: Mechanistic and Synthetic Aspects

The Ir-catalyzed conversion of prochiral tert-cyclobutanols to β-methyl-substituted ketones proceeds under comparably mild conditions in toluene (45–110 °C) and is particularly suited for the enantioselective desymmetrization of β-oxy-substituted substrates to give products with a quaternary chirality center with up to 95 % ee using DTBM-SegPhos as a chiral ligand. Deuteration experiments and kinetic isotope effect measurements revealed major mechanistic differences to related RhI-catalyzed transformations. Supported by DFT calculations we propose the initial formation of an IrIII hydride intermediate, which then undergoes a β-C elimination (C?C bond activation) prior to reductive C?H elimination. The computational model also allows the prediction of the stereochemical outcome. The Ir-catalyzed cyclobutanol cleavage is broadly applicable but fails for substrates bearing strongly coordinating groups. The method is of particular value for the stereo-controlled synthesis of substituted chromanes related to the tocopherols and other natural products.

Synthetic method 4 - alkoxyphenol compounds

The invention discloses a synthetic method of 4 - alkoxyphenol compounds, and belongs to the field of organic chemical synthesis. The method is as follows: An aryl alkyl ether compound is added to the sealing tube. The catalyst dimerization acetic acid rhodium and the oxidizing agent iodobenzene diethyl ester are added, a solvent trifluoroacetic anhydride is added, and the 4 -alkoxyphenol compound is prepared by heating reaction. To the invention, high regioselectivity direct hydroxylation of the aryl alkyl ether compound is realized, the application range of the substrate is wide, the yield is high, the activity after amplification reaction does not significantly decay, and higher yield is still obtained. The utility model has good practicability and industrial application prospect.

Para -Selective hydroxylation of alkyl aryl ethers

para-Selective hydroxylation of alkyl aryl ethers is established, which proceeds with a ruthenium(ii) catalyst, hypervalent iodine(iii) and trifluoroacetic anhydride via a radical mechanism. This protocol tolerates a wide scope of substrates and provides a facile and efficient method for preparing clinical drugs monobenzone and pramocaine on a gram scale.

From simple phenols to potent chain-breaking antioxidants by transposition of benzo[1,4]oxathiines to benzo[b]thiophenes

Simple phenols, including food stock recycled derivatives, were used for the synthesis of 1,4-benzooxathiine intermediates, with limited or no antioxidant activity. Depending upon their substitution pattern, these compounds, through an acid promoted transposition, can be converted into o-hydroxydihydrobenzo[b]thiophenes or o-hydroxy-benzo[b]thiophenes as a new class of potent chain-breaking antioxidants, showing, in the reaction with alkyl peroxyl radicals, kinetic rate constants (kinh) comparable to that of α?tocopherol, the more potent natural lipophilic phenolic antioxidant.

Regioselective synthesis of gentisyl alcohol-type marine natural products

Gentisyl alcohol-type natural products, possessing various important biological properties, have been synthesized from 4-methoxyphenol by using a selective phenol monohydroxymethylation/monochlorination, a CAN oxidation and a sodium dithionite reduction as the key steps. The natural product synthesis is efficient, atom- and step-economical, and requires no protecting groups.

Tripodal O-N-O Bis-Phenolato Amine Titanium(IV) Complexes Show High in vitro Anti-Cancer Activity

The octahedral titanium(IV) complexes trans,mer-[Ti{R3N(CH2C6H2-2-O-4-R2-6-R1)2}2] (R1 = Me, OMe, Cl; R2 = Me, OMe, F, Cl; R3 = Me, Et; not all combinations) are synthesised in two steps from simple phenols in 36–53 % overall yield. The highly crystalline (4 X-ray structures) complexes are active against MCF-7 (breast) and HCT-116 (colon) cancer cell lines showing widely varying GI50 values in the range 1–100 μM depending on R1–R3. Highest activities are realised when R1 = OMe and R2, R3 = Me (GI50 ca. 1 μM for MCF-7 and 2–3 μM for HCT-116). These are respectively 8× and 3× times greater than the activities of cisplatin in the same cell lines. These titanium complexes show some significant selectivity for cancer cell lines; up to 7× higher in MCF-7 compared to non-cancer (MRC-5) fibroblast cells. Details of cellular mode of action indicators (cell cycle perturbation, Annexin V, γ-H2AX, and caspase studies) that point to an apoptosis mode for the most active compound (R1 = OMe and R2, R3 = Me) are also reported.||||||.

Metal-Free Electrocatalytic Aerobic Hydroxylation of Arylboronic Acids

Hydroxylation of arylboronic acids to aryl alcohols was realized by a scalable electrocatalytic method. The present electrochemical hydroxylation employs low-cost methyl viologen as an organic cathodic electrocatalyst and involves O2 as a green and sustainable reactant. The electrochemical kinetic studies shown here can be a powerful tool to gain rich mechanistic and kinetic information and thus an in-depth understanding of the electrocatalytic mechanism.

Examination of Selectivity in the Oxidation of ortho- and meta-Disubstituted Benzenes by CYP102A1 (P450 Bm3) Variants

Cytochrome P450 CYP102A1 (P450 Bm3) variants were used to investigate the products arising from the P450 catalysed oxidation of a range of disubstituted benzenes. The variants used all generated increased levels of metabolites compared to the wild-type enzyme. With ortho-halotoluenes up to six different metabolites could be identified whereas the oxidation of 2-methoxytoluene generated only two aromatic oxidation products. Addition of an ethyl group markedly shifted the selectivity for oxidation to the more reactive benzylic position. Epoxidation of an alkene was also preferred to aromatic oxidation in 2-methylstyrene. Significant minor products arising from the migration of one substituent to a different position on the benzene ring were formed during certain P450-catalysed substrate turnovers. For example, 2-bromo-6-methylphenol was formed from the turnover of 2-bromotoluene and the dearomatisation product 6-ethyl-6-methylcyclohex-2,4-dienone was generated from the oxidation of 2-ethyltoluene. The RLYF/A330P variant altered the product distribution enabling the generation of certain metabolites in higher quantities. Using this variant produced 4-methyl-2-ethylphenol from 3-ethyltoluene with ≥90 % selectivity and with a biocatalytic activity suitable for scale-up of the reaction.

Direct synthesis of anilines and nitrosobenzenes from phenols

A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution (iSOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.

Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions

The combination of Cu(acac)2 and N,N′-bis(4-hydroxyl-2,6-dimethylphenyl)oxalamide (BHMPO) provides a powerful catalytic system for hydroxylation of (hetero)aryl halides. A wide range of (hetero)aryl chlorides bearing either electron-donating or -withdrawing groups proceeded well at 130 °C, delivering the corresponding phenols and hydroxylated heteroarenes in good to excellent yields. When more reactive (hetero)aryl bromides and iodides were employed, the hydroxylation reactions completed at relatively low temperatures (80 and 60 °C, respectively) at low catalytic loadings (0.5 mol % Cu).