51699-89-9

Usage

Uses

Used in Pharmaceutical Synthesis:
2,6-dibromo-4-methylanisole is used as an intermediate in the synthesis of pharmaceuticals for its ability to be readily incorporated into complex organic molecules. Its presence in the synthesis process can enhance the properties of the final product, such as stability, efficacy, or bioavailability.
Used in Organic Compound Synthesis:
In the field of organic chemistry, 2,6-dibromo-4-methylanisole is used as a building block for the creation of various organic compounds. Its unique structure, featuring two bromine atoms attached to the aromatic ring, allows for versatile chemical reactions that can lead to the development of new materials and substances.
Environmental Considerations:
2,6-dibromo-4-methylanisole is considered potentially hazardous to the environment. Therefore, it is crucial to handle and dispose of this chemical with care, adhering to safety protocols and regulations to minimize its environmental impact. Proper handling practices include the use of personal protective equipment, containment during use, and safe disposal methods to prevent contamination of soil, water, and air.

InChI:InChI=1/C8H8Br2O/c1-5-3-6(9)8(11-2)7(10)4-5/h3-4H,1-2H3

Upstream product

• 2432-14-6 3,5-dibromo-4-hydroxytoluene 
• 74-88-4 methyl iodide 
• 106-44-5 p-cresol 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 137639-64-6 3-bromo-2-methoxy-5-methylphenol 
• 945495-99-8 1,3-bis(diphenylphosphino)-2-methoxy-5-methylbenzene 
• 108940-96-1 3,5-dibromo-4-methoxybenzaldehyde 
• 13670-73-0 3,5-dibromo-4-methoxyphenol 
• 74076-59-8 2,6-dibromo-1,4-dimethoxybenzene 
• 120185-74-2 2,4-dibromo-3,6-dimethoxybenzyl chloride 
• 120185-75-3 2,4-dibromo-3,6-dimethoxyphenyl acetonitrile 
• 120185-76-4 2,4-dibromo-3,6-dimethoxyphenyl acetic acid 
• 1055414-54-4 4-methyl-2,6-bis(trifluoroacetyl)anisole 
• 6443-69-2 3,4,5-trimethoxytoluene 
• 68278-85-3 3-bromo-4,5-dimethoxy-toluene 
• 494-99-5 1,2-dimethoxy-4-methylbenzene 
• 35050-88-5 2,6-diethyl-4-methylphenol 
• 1612866-71-3 1,3-diethyl-2-methoxy-5-methylbenzene 

Relevant academic research and scientific papers

Molybdenum and Tungsten Alkylidene Complexes That Contain a 2-Pyridyl-Substituted Phenoxide Ligand

In the interest of preparing molybdenum and tungsten alkylidene complexes for olefin metathesis that are longer-lived at high temperatures (～150 °C or above), we synthesized complexes that contain a phenoxide ligand with a 2-pyridyl in one ortho position and a mesityl (Mes) or 2,4,6-i-Pr3C6H2 (Trip) in the other ortho position ([MesON]- or [TripON]-, respectively). The alkylidene (neophylidene) complexes that were prepared include W(O)(CHCMe2Ph)(Me2Pyr)(RON) (R = Mes or Trip), Mo(NC6F5)(CHCMe2Ph)(RON)Cl, Mo(N-2,6-Me2C6H3)(CHCMe2Ph)(RON)Cl, Mo(N-t-Bu)(CHCMe2Ph)(RON)Cl, and M(N-2,6-i-Pr2C6H3)(CHCMe2Ph)(TripON)(OTf) (M = Mo or W). The reaction between Mo(NAr)(CHCMe2Ph)(TripON)(OTf) and ethylene yielded an ethylene complex, Mo(NAr)(C2H4)(TripON)(OTf)(ether). All neophylidene complexes were essentially unreactive toward terminal olefins at 22 °C and showed modest homocoupling activity (at 80 or 100 °C) and alkane metathesis activity (at 150 and 200 °C). W(O)(CHCMe2Ph)(Me2Pyr)(MesON) also stereoselectively polymerized several substituted norbornadienes at 100 °C.

Three-component asymmetric catalytic ugi reaction - Concinnity from diversity by substrate-mediated catalyst assembly

The first chiral catalyst for the three-component Ugi reaction was identified as a result of a screen of a large set of different BOROX catalysts. The BOROX catalysts were assembled in situ from a chiral biaryl ligand, an amine, water, BH3×SMe2, and an alcohol or phenol. The catalyst screen included 13 different ligands, 12 amines, and 47 alcohols or phenols. The optimal catalyst system (LAP 8-5-47) provided α-amino amides from an aldehyde, a secondary amine, and an isonitrile with excellent asymmetric induction. The catalytically active species is proposed to be an ion pair that consists of the chiral boroxinate anion and an iminium cation. Harmonious arrangement of parts: A screen of BOROX catalysts that were generated in situ from 13 different ligands and 47 alcohols led to the identification of an effective combination for the catalytic asymmetric three-component Ugi reaction. Experimental results suggest that the catalyst is a chiral polyborate anion, which then forms an ion pair with the iminium cation that is generated from aldehyde and secondary amine.

Aromatization via a dibromination-double dehydrobromination sequence: A facile and convenient synthetic route to 2,6-bis(trifluoroacetyl)phenols

An efficient and reliable method to synthesize 2,6-bis(trifluoroacetyl) phenols bearing various substituents in the 4-po-sition was developed. These valuable fluorinated building blocks were obtained from the corresponding cyclohexanones in a facile and convenient procedure, demonstrated to be superior to the traditional approaches. The application of this methodology to cyclohex-ane-1,4-dione opened access to 2,5-bis(polyfluoroacyl)-1,4- hydroquinones. Structural peculiarities of the obtained phenols as well as their 1,3-dicarbonyl or 1,3,5-tricarbonyl precursors are discussed on the basis of multinuclear NMR spectroscopy.

Process development of the synthesis of 3,4,5-trimethoxytoluene

3,4,5-Trimethoxytoluene (TMT) was synthesized, starting from p-cresol, through bromination followed by methylation to give 3,5-dibromo-4-methoxytoluene (DBMT). The methoxylation of the latter with sodium methoxide in methanol was studied under pressure and by continuous distillation of the solvent, methanol. The O-methylation reaction preceding the methoxylation was advantageous from the point of view of separation, purification, and isolation of the desired product and also in reducing the tar formation. The residue obtained was minimized to 0.6-0.7 wt % of the DBMT. The methoxylation reaction with distillative removal of methanol gave a conversion of 98% of DBMT to the mixture of methoxylated products, and the conversion to TMT was 86.5% as compared to 93% and 70.81%, respectively, when the reaction was carried out under pressure in a sealed reactor. However, the overall conversion to TMT based on p-cresol is 64.27% for the methoxylation reaction under pressure and 78.46% for the reaction by continuous removal of methanol calculated as isolated yield. The advantages of the methoxylation of the DBMT over the published literature procedures involving direct methoxylation of 3,5-dibromo-p-cresol followed by methylation of the dimethoxy-p-cresol are the ease of separation, purification, and isolation by vacuum fractionation of the desired product TMT.

SYNTHETIC STRATEGIES BASED ON AROMATIC METALATION - CROSS COUPLING LINKS. REGIOSPECIFIC SYNTHESIS OF THE PHENANTHRENE NATURAL PRODUCT GYMNOPUSIN

An efficient synthesis of gymnopusin (2) using ortho metalation, Suzuki cross coupling, and new anionic Fries rearrangement (3) steps has been achieved.