576-22-7

Usage

Uses

Used in Organic Synthesis:
2-Bromo-m-xylene is used as an intermediate in organic synthesis for the preparation of various compounds. One notable example is the synthesis of 2,2',4,6,6'-pentamethylbiphenyl, a compound with potential applications in different industries. The unique chemical properties of 2-Bromo-m-xylene, such as its bromine atom and the presence of methyl groups, make it a valuable building block for creating complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Bromo-m-xylene can be used as a starting material for the synthesis of various drugs and drug candidates. Its reactivity and structural features allow for the development of new molecules with potential therapeutic applications.
Used in Chemical Research:
2-Bromo-m-xylene is also utilized in chemical research for studying reaction mechanisms, exploring new synthetic routes, and understanding the properties of bromo-xylenes. Its clear, colorless to yellow liquid form makes it an ideal candidate for various experimental setups and analytical techniques.

InChI:InChI=1/C8H9Br/c1-6-4-3-5-7(2)8(6)9/h3-5H,1-2H3

Upstream product

• 593-53-3 Methyl fluoride 
• 95-46-5 2-methylphenyl bromide 
• 75-25-2 Bromoform 
• 103724-97-6 4-Chloro-1,2-dimethylcyclopentene 
• 583-70-0 1-bromo-2,4-dimethylbenzene 
• 75366-04-0 2-methyl-1H-cyclopropabenzene 
• 108-38-3 m-xylene 
• 5345-05-1 4-t-butyl-2,6-dimethylbromobenzene 
• 87-62-7 2,6-dimethylaniline 
• 632-46-2 2,6-dimethylbenzoic acid 
• 92-52-4 biphenyl 
• 17961-82-9 (2,6-dimethylphenyl)trimethylsilane 
• 98-19-1 5-tert-Butyl-m-xylene 

Downstream Products

• 36669-06-4 dimethyl 2-hydroxyisophthalate 
• 39622-80-5 1,3-dimethyl 2-bromobenzene-1,3-dicarboxylate 
• 30595-80-3 2-(2',6'-dimethylphenyl)-ethanol 
• 62285-58-9 2,6-dimethylbenzyl alcohol 
• 18153-44-1 9-(2,6-dimethylphenyl)-9-fluorenol 
• 54521-25-4 (2,6-dimethyl-benzyl)-dimethyl-amine 
• 632-46-2 2,6-dimethylbenzoic acid 
• 25115-80-4 2,6-Dimethylphenyl-tert-butylketon 
• 2142-76-9 2',6'-dimethylacetophenone 
• 1587-05-9 2-allyl-1,3-dimethylbenzene 
• 80445-61-0 E-1<1-(2,6-dimethylphenyl)>-2-buten-1-ol 
• 74331-74-1 2,6-dimethylphenylacetylene 
• 87871-29-2 1-(2,6-dimethylphenyl)-2,2-dimesitylethenol 
• 148706-33-6 (S)-3-[(2S,3S)-2-Bromo-3-(2,6-dimethyl-phenyl)-butyryl]-4-phenyl-oxazolidin-2-one 

Relevant academic research and scientific papers

A Tethered Tolane: Twisting the Excited State

The synthesis of a doubly bridged tolane is reported. The target is obtained in a five-step synthesis, starting from commercially available 2-amino-meta-xylene by a combination of a Sandmeyer reaction, radical bromination, and Stille-type coupling, followed by double ring closing. The doubly tethered tolane is crystalline; the two phenyl rings are highly twisted with respect to each other both in solution and in the solid state. Optical spectroscopy and quantum chemical calculations show that the doubly bridged tolane is twisted not only in the ground state, but also in the excited state, leading to emission from the twisted state in solution and in the solid state. Strong phosphorescence is observed at cryogenic temperatures.

Synthesis and biological evaluation of thielocin B1 analogues as protein-protein interaction inhibitors of PAC3 homodimer

The synthesis and biological evaluation of thielocin B1 analogues have been demonstrated. Fourteen analogues modified in the central core and terminal carboxylic acid moiety were concisely synthesized by simple esterification or etherification reaction. The evaluation of synthetic analogues as inhibitors of proteasome assembling chaperone (PAC) complexes (the PAC3 homodimer and PAC1/PAC2) revealed that the natural product-like bending structure and terminal carboxylic acid groups were crucial for its biological activity. Moreover, SAR and in silico docking studies indicated that all methyl groups on the diphenyl ether moiety of thielocin B1 contribute to the potent and selective inhibition of the PAC3 homodimer via hydrophobic interactions.

Transition-metal-free decarboxylative bromination of aromatic carboxylic acids

Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.

Process for Preparing Chloro-and Bromoaromatics

The present invention relates to a novel process for preparing chloro- or bromoaromatics of the formula (II) by diazotizing the formula (I) by means of sodium nitrite or potassium nitrite in the presence of aqueous hydrochloric or hydrobromic acids and then reacting with an iron(II) or iron(III) compound, optionally in the presence of additional amounts of hydrogen chloride or hydrogen bromide or alkali metal or alkaline earth metal chlorides or bromides.

Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylisulfonium halides generated in situ

Halodimethylsulfonium halide 1, which is readily formed in situ from hydrohaloic acid and DMSO, is a good nucleophilic halide. This activated nucleophilic halide rapidly converts aryldiazonium salt prepared in situ by the same hydrohaloic acid and nitrite ion to aryl chlorides, bromides, or iodides in good yield. The combined action of nitrite ion and hydrohaloic acid in DMSO is required for the direct transformation of aromatic amines, which results in the production of aryl halides within 1 h. Substituted compounds with electron-donating or -withdrawing groups or sterically hindered aromatic amines are also smoothly transformed to the corresponding aromatic halides. The only observed by-product is the deaminated arene (usually 7%). The isolated aryldiazonium salts can also be converted to the corresponding aryl halides using 1. The present method offers a facile, one-step procedure for transforming aminoarenes to haloarenes and lacks the environmental pollutants that usually accompany the Sandmeyer reaction using copper halides.

Efficient method for the preparation of aromatic bromides and iodides by ferrocenium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate-catalyzed halogenation with bromine and iodine monochloride

Direct iodination and bromination of various aromatic compounds with 1.1-2.0 molar amounts of iodine monochloride (ICl) and 1.1-3.0 molar amounts of bromine proceeded smoothly to afford the corresponding aromatic iodides and bromides, respectively, in good to excellent yields by using 0.05 molar amount of ferrocenium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate, Cp2FeB[3,5-(CF3)2C6H 3]4 (1), in the presence of ZnO. Iodination of toluene in the co-existence of 0.5 molar amount of DDQ also proceeded to give iodotoluenes in high yield.

Aromatic Spiranes XX [1]: Syntheses of Dimethylsubstituted 2-Carboxymethyl-indan-1-ones and Benzylchlorides as Synthones for Syntheses of di- to tetramethylsubstituted Spirobiindandiones

The isomeric dimethyl methylbenzoates 5, obtained from the bromides via Grignard reactions with dimethylcarbonate, were reduced with LiAlH4 to the hydroxymethyl derivatives 6. The latter were then transformed both to the benzylchlorides 7 (with SOCl2) and to the aldehydes 8 (with pyridinium chlorochromate). Knoevenagel-Doebner reaction of 8 afforded the acrylic acids 9 which (after hydrogenation to 11) were cyclized to the desired indanones 12 with polyphosphoric acid. On the other hand, 12c and 12e were prepared from dimethyl 3-chloropropiophenone (14) by warming with sulfuric acid. After NaH-catalyzed reaction with dimethylcarbonate, the indanones 12 gave the ketoesters 15 which then could be hydrogenated to the indanes 16. All reactions proceeded with satisfactory to excellent yields (60-90%).