90875-08-4

Usage

Uses

Used in Pharmaceutical Industry:
(rac)-4-(2-bromopropyl)-1-methoxybenzene is used as an intermediate in the synthesis of various pharmaceuticals for [application reason]. Its unique structure allows for the creation of a diverse range of medicinal compounds, contributing to the development of new drugs and therapies.
Used in Agrochemical Industry:
In the agrochemical industry, (rac)-4-(2-bromopropyl)-1-methoxybenzene is used as a key component in the development of pesticides, herbicides, and other agricultural chemicals for [application reason]. Its versatility in chemical reactions enables the production of effective and targeted agrochemicals to improve crop protection and yield.
Used in Fine Chemicals Industry:
(rac)-4-(2-bromopropyl)-1-methoxybenzene is also utilized as an intermediate in the production of fine chemicals for [application reason]. These fine chemicals can be found in a variety of applications, such as fragrances, dyes, and specialty chemicals, where their unique properties are highly valued.

Upstream product

• 140-67-0 Estragole 
• 131029-01-1 1-(4-methoxyphenyl)propan-2-ol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 122-84-9 4-methoxybenzyl methyl ketone 

Downstream Products

• 1028202-17-6 1-methoxy-4-(2-methyl-5-phenylpentyl)benzene 
• 1239477-82-7 (rac)-1-methoxy-4-[2-(phenylsulfonyl)propyl]benzene 
• 93014-82-5 (rac)-1-methoxy-4-(2-phenylpropyl)benzene 
• 4646-94-0 2-(4-methoxyphenyl)-n-butanoic acid 

Relevant academic research and scientific papers

HBr–DMPU: The First Aprotic Organic Solution of Hydrogen Bromide

HBr and DMPU (1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone) form a room-temperature-stable complex that provides a mild, effective, and selective hydrobrominating reagent toward alkynes, alkenes, and allenes. HBr–DMPU could also replace other halogenating reagents in the halo-Prins reaction, ether cleavage, and deoxy-bromination reactions.

Iron-catalyzed borylation of alkyl electrophiles

The use of low-cost iron(III) acetoacetate (Fe(acac)3) and tetramethylethylenediamine (TMEDA) enables the direct cross-coupling of alkyl halides with bis(pinacolato)diboron. This approach allows for the borylation of activated or unactivated primary, secondary, and tertiary bromides. Moreover, even the borylation of benzylic or allylic chlorides, tosylates, and mesylates are possible. The reactions proceed under mild conditions at room temperature and show broad functional-group compatibility and "robustness" as measured by a modified Glorius robustness screen.

Iron-catalyzed cross-coupling of unactivated secondary alkyl thio ethers and sulfones with aryl grignard reagents

The first systematic investigation of unactivated aliphatic sulfur compounds as electrophiles in transition-metal-catalyzed cross-coupling are described. Initial studies focused on discerning the structural and electronic features of the organosulfur substrate that enable the challenging oxidative addition to the C(sp3)-S bond. Through extensive optimization efforts, an Fe(acac)3-catalyzed cross-coupling of unactivated alkyl aryl thio ethers with aryl Grignard reagents was realized in which a nitrogen "directing group" on the S-aryl moiety of the thio ether served a critical role in facilitating the oxidative addition step. In addition, alkyl phenyl sulfones were found to be effective electrophiles in the Fe(acac) 3-catalyzed cross-coupling with aryl Grignard reagents. For the latter class of electrophile, a thorough assessment of the various reaction parameters revealed a dramatic enhancement in reaction efficiency with an excess of TMEDA (8.0 equiv). The optimized reaction protocol was used to evaluate the scope of the method with respect to both the organomagnesium nucleophile and sulfone electrophile.