20531-93-5

Usage

Structure

A derivative of benzene with two methyl groups at the 1 and 3 positions, and a prop-2-en-1-yloxy group at the 5 position.

Applications

a. Production of various organic compounds
b. Chemical intermediate in the synthesis of pharmaceuticals, agrochemicals, and industrial chemicals
c. Production of fragrances and flavorings due to its aromatic properties
d. Precursor in the manufacture of polymers and plastics

Safety

Should be handled and used in accordance with proper safety measures and guidelines due to potential health and environmental hazards.

Upstream product

• 37621-81-1 sodium 3,5-dimethylphenolate 
• 106-95-6 allyl bromide 
• 205981-42-6 1,3-Dimethyl-5-[((Z)-propenyl)oxy]-benzene 
• 108-68-9 3,5-Dimethylphenol 
• 1200591-16-7 C₁₂H₁₄O₃ 

Downstream Products

• 26489-75-8 2-allyl-3,5-dimethylphenol 
• 80448-11-9 1-(dimethylamino)-2-acetoxy-3-(3,5-dimethylphenoxy)propane 
• 80448-10-8 1-(diethylamino)-2-acetoxy-3-(3,5-dimethylphenoxy)propane 
• 205981-42-6 1,3-Dimethyl-5-[((Z)-propenyl)oxy]-benzene 
• 126707-92-4 4,6-dimethyl-2-(phenylthiomethyl)-2,3-dihydrobenzofuran 
• 126734-06-3 5-Chloro-4,6-dimethyl-2-phenylsulfanylmethyl-2,3-dihydro-benzofuran 
• 126708-21-2 4,6-dimethyl-5-(phenylthio)-2-(phenylthiomethyl)-2,3-dihydrobenzofuran 
• 138376-23-5 3,5-dimethylphenyl propyl ether 
• 108-68-9 3,5-Dimethylphenol 
• 54756-71-7 2-allyl-3,5-dimethyl-anisole 
• 26489-79-2 4-Allyl-3,5-dimethylphenol 

Relevant academic research and scientific papers

ORGANIC COMPOUNDS

Disclosed are TRPM8 modulators as defined by formula (I) for achieving a cooling effect on skin and mucousa.

Enantioselective Construction of Si-Stereogenic Center via Rhodium-Catalyzed Intermolecular Hydrosilylation of Alkene

Catalytic, enantioselective synthesis of stereogenic silicon compounds remains a challenge. Herein, we report a rhodium-catalyzed regio- and enantio-selective intermolecular hydrosilylation of alkene with prochiral dihydrosilane. This new method features a simple catalytic system, mild reaction conditions and a wide functional group tolerance.

Nonracemic Dimethylphenyl Glycerol Ethers in the Synthesis of Physiologically Active Aminopropanols

Six regioisomeric nonracemic dimethylphenyl glycerol ethers were synthesized by asymmetric dihydroxylation of the corresponding allyl dimethylphenyl ethers. The enantioselectivity of the reaction with o-methyl derivatives was lower (down to 34% ee) than with m-methylphenyl ethers (up to 86% ee). Enantiomeric 3-(3,4-dimethylphenoxy)propane-1,2-diols were used to obtain enantiomerically pure physiologically active amino alcohols and their derivatives.

Enantioselective Vanadium-Catalyzed Oxidative Coupling: Development and Mechanistic Insights

The evolution of a more reactive chiral vanadium catalyst for enantioselective oxidative coupling of phenols is reported, ultimately resulting in a simple monomeric vanadium species combined with a Br?nsted or Lewis acid additive. The resultant vanadium complex is found to effect the asymmetric oxidative ortho-ortho coupling of simple phenols and 2-hydroxycarbazoles with good to excellent levels of enantioselectivity. Experimental and quantum mechanical studies of the mechanism indicate that the additives aggregate the vanadium monomers. In addition, a singlet to triplet crossover is implicated prior to carbon-carbon bond formation. The two lowest energy diastereomeric transition states leading to the enantiomeric products differ substantially with the path to the minor enantiomer involving greater torsional strain between the two phenol moieties.

Facile one-pot synthesis of aliphatic bridged diaryloxy compounds, cyclic and crown ethers under mild conditions

We report here the facile, room temperature, catalyst free, one pot synthesis of aliphatic bridged diaryloxy compounds, cyclic and crown ethers. Anhydrous potassium carbonate (K2CO3) as a mild base along with dimethyl sulfoxide gener

Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles

The first examples of asymmetric oxidative coupling of simple phenols and 2-hydroxycarbazoles are outlined. Generation of a more vanadium catalyst by ligand design and by addition of an exogenous Br?nsted or Lewis acid was found to be key to coupling the more oxidatively resistant phenols. The resultant vanadium complex is both more Lewis acidic and more strongly oxidizing. Good to excellent levels of enantioselectivity could be obtained, and simple trituration readily provided the products with ≥95% ee.

PdI2-catalyzed regioselective cyclocarbonylation of 2-allyl phenols to dihydrocoumarins

A simple, efficient, and regioselective synthesis of 3-methyl-3,4-dihydrocoumarins is reported. The reaction of 2-allyl phenols with synthesis gas was catalyzed by PdI2, and 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane (L1) and 1,3,5,7-tetramethyl-6-tetradecyl-2,4,8-trioxa-6-phosphaadamantane (L2) were effective as ligands, affording good product selectivity in all cases.

Design, synthesis and cytotoxic activities of novel hybrid compounds between dihydrobenzofuran and imidazole

A series of novel hybrid compounds between dihydrobenzofuran and imidazole has been prepared and evaluated in vitro against a panel of human tumor cell lines. The results suggest that substitution of the imidazolyl-1-position with an electron-donating dihydrobenzofuran, and the imidazolyl-3-position with a naphthylacyl or electron-rich phenacyl group, were vital for modulating cytotoxic activity.

Radical chain reduction of alkylboron compounds with catechols

The conversion of alkylboranes to the corresponding alkanes is classically per-formed via protonolysis of alkylboranes. This simple reaction requires the use of severe reaction conditions, that is, treatment with a carboxylic acid at high temperature (>150 °C). We report here a mild radical procedure for the transformation of organoboranes to alkanes. 4-tert-Butylcatechol, a well-established radical inhibitor and antioxidant, is acting as a source of hydrogen atoms. An efficient chain reaction is observed due to the exceptional reactivity of phenoxyl radicals toward alkylboranes. The reaction has been applied to a wide range of organoboron derivatives such as B- alkylcatecholboranes, trialkylboranes, pinacolboronates, and alkylboronic acids. Furthermore, the so far elusive rate constants for the hydrogen transfer between secondary alkyl radical and catechol derivatives have been experimentally determined. Interestingly, they are less than 1 order of magnitude slower than that of tin hydride at 80 °C, making catechols particularly attractive for a wide range of transformations involving C-C bond formation.

Regioselective iron-catalyzed decarboxylative allylic etherification

[Chemical Equation Presented] An anionic iron complex catalyzes the decarboxylative allylation of phenols to form allylic ethers in high yield. The allylation is regioselective rather than regiospecific. This suggests that the allylation proceeds through π-allyl iron intermediates in contrast to related allylations of carbon nucleophiles that have been proposed to proceed via π-allyl complexes. Ultimately, iron catalysts have the potential to replace more expensive palladium catalysts that are typically utilized for decarboxylative couplings.