5307-05-1

Basic information

• Product Name: 4-Methoxy-2-methylphenol
• Synonyms: 2-Methyl-4-methoxyphenol;4-Methoxy-2-methylphenol
• CAS NO: 5307-05-1
• Molecular Formula: C₈H₁₀O₂
• Molecular Weight: 138.17
• Mol File: 5307-05-1.mol
• Article Data: 26

Chemical Properties

• Melting Point: 71 °C
• Boiling Point: 127-128 °C(Press: 11 Torr)
• Appearance: /
• Density: 1.078±0.06 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 10.80±0.18(Predicted)
• CAS DataBase Reference: 4-Methoxy-2-methylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxy-2-methylphenol(5307-05-1)
• EPA Substance Registry System: 4-Methoxy-2-methylphenol(5307-05-1)

Safety Data

• Hazardous Substances Data: 5307-05-1(Hazardous Substances Data)

Usage

General Description

4-Methoxy-2-methylphenol, also known as guaiacol, is a chemical compound that belongs to the category of phenolic compounds. It is a colorless to pale yellow liquid with a distinct smoky, spicy odor. Guaiacol is commonly used as a flavoring agent in the food industry, particularly in the production of vanilla and coffee flavors. It is also employed as an intermediate in the synthesis of various pharmaceuticals, dyes, and fragrances. Additionally, guaiacol has been investigated for its potential use in the treatment of tuberculosis and other respiratory diseases due to its antiseptic and expectorant properties. Overall, guaiacol has a wide range of applications in different industries, making it a valuable and versatile chemical compound.

Upstream product

• 23562-77-8 2-(dimethylaminomethyl)-4-methoxyphenol 
• 3019-89-4 sodium 3-methylphenoxide 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 95-71-6 2-methylbenzene-1,4-diol 
• 77-78-1 dimethyl sulfate 
• 50-00-0 formaldehyd 
• 150-76-5 4-methoxy-phenol 
• 41951-76-2 2-hydroxy-5-methoxybenzyl alcohol 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 208399-66-0 4-methoxy-2-methylphenyl boronic acid 
• 27060-75-9 4-bromo-3-methylanisole 
• 13334-71-9 1-chloro-4-methoxy-2-methylbenzene 
• 52289-54-0 4-methoxysalicylaldehyde 
• 67-56-1 methanol 

Downstream Products

• 5600-81-7 2-Hydroxy-5-methoxy-3-methylbenzylalkohol 
• 93728-08-6 Bis-<2-hydroxy-5-methoxy-3-methyl-phenyl>-methan 
• 936247-40-4 C₁₁H₁₀BrNO₂S 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 95-71-6 2-methylbenzene-1,4-diol 
• 66584-31-4 3-methoxy-5-methylphenylamine 
• 13522-81-1 4-methoxy-2-methylphenyl acetate 
• 57197-11-2 4,4-dimethoxy-2-methylcyclohexane-2,5-dien-1-one 
• 61552-31-6 benzyl 2-methyl-4-methoxyphenyl ether 
• 10373-90-7 4-Methoxy-2-methyl-cyclohexanol 
• 91-86-1 (2RS,4'R,8'R)-7-Methyl-tocol 
• 119-13-1 dl-δ-tocopherol 
• 121600-35-9 4-Methoxy-2-methyl-5-((7R,11R)-trans-phytyl)-phenol 

Relevant articles and documents

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.

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.

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.