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Usage

Uses

Used in Organic Synthesis:
1-bromo-4-methoxy-2,3,5,6-tetramethylbenzene serves as a precursor in the synthesis of various organic compounds. Its unique structure allows for the creation of a wide range of molecules, making it a versatile building block in organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical field, 1-bromo-4-methoxy-2,3,5,6-tetramethylbenzene is utilized as an intermediate for the development of new drugs. Its specific molecular features contribute to the design and synthesis of pharmaceutical agents with potential therapeutic applications.
Used in Agrochemical Industry:
1-bromo-4-methoxy-2,3,5,6-tetramethylbenzene also finds applications in the agrochemical sector, where it is employed as a starting material for the production of various agrochemicals. Its properties enable the creation of compounds that can be used in crop protection and other agricultural applications.

Upstream product

• 14337-37-2 2,3,5,6-tetramethylanisole 

Downstream Products

• 1208459-70-4 (4-methoxy-2,3,5,6-tetramethyl)-phenyl boronic acid 

Relevant academic research and scientific papers

Syntheses of extreme sterically hindered 4-methoxyboronic acids

4-Iodoanisoles 3a,b, 3d and 4-bromoanisoles 4a-d were readily obtained. An extreme steric hindrance precluded obtaining 3c. Catalytic borylation of 3a,b, 3d followed by hydrolysis of boronic ester 26a,b, 26d easily provided the boronic acids 5a,b, 5d. Com

Nuclear versus Side-Chain Bromination of Methyl-Substituted Anisoles by N-Bromosuccinimide

The reactions of methyl-substituted anisoles with N-bromosuccinimide in CCl4 are reported.In the absence of a catalyst and under irradiation, some of these substrates undergo nuclear bromination in competition with the well-known side-chain bromination.With 2-methylanisole and with 2,6-dimethylanisole, nuclear bromination is not observed, whereas with 3,5-dimethylanisole, nuclear bromination at the 4-position is the dominating reaction.Investigation of the reactivity of several other methyl-substituted anisoles revealed the following general trend: methyl-substituted anisoles are attacked at the position para to the methoxy group rather than at the side chain when (at least) two methyl groups are present at positions 3 and 5.When positions 2 and 6 are both occupied, nuclear bromination is retarded; in 2,6-dimethylanisole and 2,3,6-trimethylanisole, only side-chain bromination is observed.In contrast, in 2,3,5,6-tetramethylanisole, the 4-position is sufficiently reactive to be brominated, because the decrease in reactivity by the presence of two methyl groups at positions 2 and 6 is overruled by the two additional methyl groups at positions 3 and 5; as a result, both nuclear and side-chain bromination occur.The observed chemospecificity can be rationalized by a difference in mechanism: the side-chain bromination is radical reaction, while the nuclear bromination is an electrophilic aromatic substitution reaction, which is so far contrary to expectation, as irradiation had been expected to favor radical processes.