50638-50-1

Usage

Uses

Used in Pharmaceutical Industry:
4-BROMO-N,N-DIMETHYL-M-TOLUIDINE is used as a chemical intermediate for the synthesis of pyridinylpyrazoleacetonitriles and pyridinylpyrazoleacetamides. These compounds serve as ROS receptor tyrosine kinase inhibitors, which play a crucial role in the development of novel therapeutic agents for various diseases, including cancer and other conditions related to the overactivation of ROS receptors.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-BROMO-N,N-DIMETHYL-M-TOLUIDINE is utilized as a key building block for the creation of more complex molecules with specific applications. Its unique structure allows for further functionalization and modification, making it a valuable component in the synthesis of various organic compounds.
Used in Research and Development:
4-BROMO-N,N-DIMETHYL-M-TOLUIDINE is also employed in research and development laboratories for the study of its chemical properties, reactivity, and potential applications in various fields. Researchers use 4-BROMO-N,N-DIMETHYL-M-TOLUIDINE to explore new reaction pathways, develop innovative synthetic methods, and investigate its potential as a precursor for the development of new drugs and materials.

InChI:InChI=1/C9H12BrN/c1-7-6-8(11(2)3)4-5-9(7)10/h4-6H,1-3H3

Upstream product

• 50-00-0 formaldehyd 
• 71642-16-5 3-methyl-2,4,6-tribromoaniline 
• 121-72-2 N,N-dimethyl-m-toluidine 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 825-80-9 m-methyl-N,N-dimethylaniline-N-oxide 
• 16518-64-2 3-(dimethylamino)benzoic acid methyl ester 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 678986-46-4 5-bromo-2-dimethylamino-4-methyl-benzyl alcohol 
• 1427470-72-1 C₉H₁₃NS 
• 80948-74-9 4-bromo-N,3-dimethylbenzenamine 
• 943635-05-0 4-(N,N-dimethylamino)-2-methylbenzamide 
• 1178884-33-7 6-dimethylamino-3,4-dihydro-2H-isoquinolin-1-one 
• 1462328-78-4 2-chloro-6-(6-dimethylamino-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)benzaldehyde 
• 1462328-86-4 2-(3-chloro-2-(hydroxymethyl)phenyl)-6-(dimethylamino)-3,4-dihydroisoquinolin-1(2H)-one 
• 1198765-28-4 C₃₄H₃₄N₆O₅ 
• 1242156-99-5 C₁₈H₁₇BrN₂O₂ 
• 1462328-58-0 C₁₃H₁₉N₃O 
• 1178884-09-7 6-(dimethylamino)-2-(2-(hydroxymethyl)-3-(1-methyl-5-(5-(morpholine-4-carbonyl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-3,4-dihydroisoquinolin-1(2H)-one 
• 65399-14-6 4-(dimethylamino)-2-methylbenzoic acid 
• 1421275-63-9 N,N,3-trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine 
• 1421275-68-4 C₂₇H₂₇N₅O 

Relevant academic research and scientific papers

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.

Synthesis of Halogenated Anilines by Treatment of N, N-Dialkylaniline N-Oxides with Thionyl Halides

The special reactivity of N,N-dialkylaniline N-oxides allows practical and convenient access to electron-rich aryl halides. A complementary pair of reaction protocols allow for the selective para-bromination or ortho-chlorination of N,N-dialkylanilines in up to 69% isolated yield. The generation of a diverse array of halogenated anilines is made possible by a temporary oxidation level increase of N,N-dialkylanilines to the corresponding N,N-dialkylaniline N-oxides and the excision of the resultant weak N-O bond via treatment with thionyl bromide or thionyl chloride at low temperature.

Making Dimethylamino a Transformable Directing Group by Nickel-Catalyzed C-N Borylation

The dimethylamino (Me2N) group is arguably the most versatile functional group capable of highly efficient and site-selective directed aromatic functionalizations at the ortho-, meta-, and para-positions depending on reaction conditions. While the repertoire of Me2N-directed reactions is growing at a rapid pace, the lack of a general method to transform this group to other functionalities hampers its wider application in organic synthesis. Here we report nickel-catalyzed C-N borylations of aryl- and benzyl-dimethylamines that permit the conversion of a huge library of largely underutilized Me2N-containing organic molecules into various functional molecules by taking advantage of the wealth of existing C-B functionalization methods.

Development of a scalable synthesis of a Bruton's tyrosine kinase inhibitor via C-N and C-C bond couplings as an end game strategy

A scalable and convergent synthesis of a BTK (Bruton's tyrosine kinase) inhibitor has been developed. Synthetic routes to key intermediates were explored for the scale-up campaign, especially the process for 6-dimethylaminodihydroisoquinolinone, which was prepared via a regioselective cyclization of an isocyanate, mediated by AlCl3. Improved routes to key building blocks were demonstrated by expedient multikilogram productions. The target compound was assembled through a Pd-catalyzed amidation reaction followed by a Suzuki-Miyaura cross-coupling reaction.

(Hetero)-aryl ketones derivatives with antibacterial properties

Conformationally restricted aryl and heteroaryl ketones derived from monic acid have useful antibacterial properties.