769-25-5

Usage

Uses

Used in Chemical Synthesis:
2,4,6-Trimethylstyrene is used as an intermediate in the production of other chemicals. It serves as a key precursor for the synthesis of various organic compounds, including 2-Methoxy-1-(2,4,6-trimethyl-phenyl)-ethanone, which is an important compound in the fragrance and flavor industry. The reactivity of 2,4,6-TMS allows for a wide range of chemical reactions, making it a versatile building block in the synthesis of various organic molecules.
Used in the Fragrance and Flavor Industry:
2,4,6-Trimethylstyrene is used as a starting material for the synthesis of 2-Methoxy-1-(2,4,6-trimethyl-phenol)-ethanone, which is an important compound in the fragrance and flavor industry. 2,4,6-TRIMETHYLSTYRENE is known for its unique aroma and is used in the production of perfumes, colognes, and other scented products. Additionally, it is used in the flavor industry to impart specific taste and aroma profiles to food and beverages.
Used in the Production of Polymers:
2,4,6-Trimethylstyrene can also be used in the production of polymers, such as polystyrene and styrene copolymers. The presence of the methyl groups on the benzene ring provides unique properties to the resulting polymers, such as increased stability, heat resistance, and chemical resistance. These polymers find applications in various industries, including packaging, automotive, and construction.
Used in the Pharmaceutical Industry:
2,4,6-Trimethylstyrene can be used as a starting material for the synthesis of various pharmaceutical compounds. Its chemical reactivity allows for the formation of a wide range of drug molecules, which can be used for the treatment of various diseases and medical conditions. The versatility of 2,4,6-TMS makes it an attractive candidate for the development of new pharmaceutical agents.

InChI:InChI=1/C11H14/c1-5-11-9(3)6-8(2)7-10(11)4/h5-7H,1H2,2-4H3

Upstream product

• 1667-01-2 2,4,6-Trimethylacetophenone 
• 75-01-4 chloroethylene 
• 2633-66-1 2-mesitylmagnesium bromide 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 593-60-2 Vinyl bromide 
• 5980-97-2 mesitylboronic acid 
• 2554-06-5 2,4,6,8-tetramethyl-2,4,6,8-tetravinyl-cyclotetrasiloxane 
• 2627-95-4 tetramethyldivinyldisiloxane 
• 74-85-1 ethene 
• 4028-63-1 iodomesitylene 
• 78-08-0 Triethoxyvinylsilane 
• 1667-04-5 2-bromomesitylene 
• 487-68-3 mesytaldehyde 

Downstream Products

• 24074-20-2 3-phenyl-5-(2,4,6-trimethyl-phenyl)-isoxazole 
• 139016-19-6 (R)-1-(2,4,6-trimethylphenyl)-1,2-ethanediol 
• 6908-41-4 4-(methoxycarbonyl)benzyl alcohol 
• 209798-32-3 2-(2',4',6'-trimethylphenyl)-1-nitro-2-trinitromethylethane 
• 50447-68-2 2-(2,4,6-trimethylphenyl)oxirane 
• 58047-52-2 2-(2,4,6-trimethylphenyl)acetaldehyde 
• 108-67-8 1,3,5-trimethyl-benzene 
• 2516-69-0 (R)-1-mesitylethanol 
• 6950-92-1 2-(2,4,6-trimethylphenyl)ethanol 
• 1517-71-1 (S)-1-(2,4,6-trimethylphenyl)ethanol 
• 213990-59-1 (2S)-2-{[(tert-butoxy)carbonyl]amino}-2-(2,4,6-trimethylphenyl)ethanol 
• 354153-47-2 (+/-)-1-(2,4,6-trimethyl-phenyl)-ethane-1,2-diol 

Relevant academic research and scientific papers

Tertiary arsine ligands for the Stille coupling reaction

The Stille coupling reaction is one of the most important coupling reactions. It is well known that the triphenylarsine ligand can accelerate the reaction rate of Stille coupling. However, other arsine ligands have never been investigated for the Stille c

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Vinyl Acetate in Dimethyl Isosorbide as a Sustainable Solvent

A nickel-catalyzed reductive cross-coupling has been achieved using (hetero)aryl bromides and vinyl acetate as the coupling partners. This mild, applicable method provides a reliable access to a variety of vinyl arenes, heteroarenes, and benzoheterocycles, which should expand the chemical space of precursors to fine chemicals and polymers. Importantly, a sustainable solvent, dimethyl isosorbide, is used, making this protocol more attractive from the point of view of green chemistry.

Methylenation for Aldehydes and Ketones Using 1-Methylbenzimidazol-2-yl Methyl Sulfone

The methylenation reagent 1-methylbenzimidazol-2-yl methyl sulfone 2 reacts with various aldehydes and ketones in the presence of t-BuOK (room temperature, 1 h) in dimethylformamide to give the corresponding terminal alkenes generally in high yields. For sensitive substrates, the reaction is better carried out at low temperature using sodium hexamethyldisilazide in 1,2-dimethoxyethane. The byproduct is easily removed from the products, and the reaction conditions are mild and practical. Reagent 2 can be easily prepared from commercially available 2-mercaptobenzimidazole 5 in 95% yield without any expensive reagents.

Donor Rhodium Carbenes by Retro-Buchner Reaction

Rhodium carbenes are key intermediates in a range of cycloadditions and insertion reactions. Herein, we report the first generation of donor RhII carbenes by decarbenation of 7-substituted 1,3,5-cycloheptatrienes. This discovery unlocks an improved retro-Buchner-cyclopropanation sequence, a Si?H insertion reaction for a broad-scope synthesis of allylsilanes, and a new method for the vinylogation of aldehydes. The last strategy led to the development of an iterative synthesis of E-polyenes, and to the total synthesis of navenones B and C.

Cyclopropanation by Gold- or Zinc-Catalyzed Retro-Buchner Reaction at Room Temperature

Through the design of a second generation of more reactive 7-substituted 1,3,5-cycloheptatrienes, a room-temperature gold(I)-catalyzed retro-Buchner-cyclopropanation sequence and the first zinc(II)-catalyzed version of this process, which uses inexpensive

Efficient and stereoselective nitration of mono- and disubstituted olefins with AgNO2 and TEMPO

Nitroolefin is a common and versatile reagent. Its synthesis from olefin is generally limited by the formation of mixture of cis and trans compounds. Here we report that silver nitrite (AgNO2) along with TEMPO can promote the regio- and stereoselective nitration of a broad range of olefins. This work discloses a new and efficient approach wherein starting from olefin, nitroalkane radical formation and subsequent transformations lead to the desired nitroolefin in a stereoselective manner.

Stereoselective nitration of olefins with tBuONO and TEMPO: Direct access to nitroolefins under metal-free conditions

Nitroolefins are essential elements for both synthetic chemistry and medicinal research. Despite significant improvements in nitration of olefin an efficient metal-free synthesis remains elusive so far. Herein, we disclose a new set of reagents to access nitroolefins in a single step under metal-free conditions. A wide range of olefins with diverse functionalities has been nitrated in synthetically useful yields. This transformation is operationally simple and exhibits excellent E-selectivity. Furthermore, site selective nitration in a complex setup makes this method advantageous.

Low pressure vinylation of aryl and vinyl halides via Heck-Mizoroki reactions using ethylene

Aryl bromides and iodides in the presence of catalytic amounts of a palladacycle derived from acetophenone oxime and 2 equiv of potassium acetate react with ethylene under ambient pressure (15-30 psi) to give the corresponding vinylarenes. The reactions work with both electron-deficient and electron-rich aryl compounds and tolerate wide variety of common functional groups. Vinyl bromides lead to 1,3-dienes in moderate yields.

Studies of microwave-enhanced Suzuki-Miyaura vinylation of electron-rich sterically hindered substrates utilizing potassium vinyltrifluoroborate

The Suzuki-Miyaura cross-coupling of sterically hindered and electron-rich ortho,ortho′-substituted aryl halides with potassium vinyltrifluoroborate utilizing microwave irradiation has been conducted while adjusting solvent ratio, irradiation time, and catalyst loading to find optimal conditions. Coupling of benzyl 3,5-bis(benzyloxy)-4-bromobenzoate leads to a mixture of the desired styrene derivative and the reduced product. 4-Bromo-1,3,5- trimethoxybenzene, methyl 4-bromo-3,5-dimethoxybenzoate, and mesitylene bromide were also coupled to test the breadth and scope of this methodology. Of these substrates tested only 4-bromo-1,3,5-trimethoxybenzene was not vinylated successfully, which is believed to be due to the electron-rich nature of this system.

SLOW RELEASE OF ORGANOBORONIC ACIDS IN CROSS-COUPLING REACTIONS

A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture: R1-B-T; where R1 represents an organic group, T represents a conformationalIy rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a pal ladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.