52488-28-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-5-nitrotoluene is used as a building block for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicine.
Used in Dye Industry:
In the dye industry, 3-Bromo-5-nitrotoluene serves as a crucial intermediate in the production of various dyes. Its chemical properties make it suitable for creating a wide range of colorants used in different applications.
Used in Agrochemical Industry:
3-Bromo-5-nitrotoluene is commonly used as an intermediate in the manufacture of agrochemicals. Its presence in these products helps improve their effectiveness in agricultural applications, such as pest control and crop protection.
Used in Rubber Chemical Industry:
3-BROMO-5-NITROTOLUENE also plays a significant role in the rubber chemical industry, where it is used as an intermediate for the production of various rubber chemicals. Its properties contribute to the enhancement of rubber products' performance and durability.
Used in Antimicrobial Agents Development:
3-Bromo-5-nitrotoluene has been found to possess antimicrobial activity, making it a potential candidate for the development of novel antimicrobial agents. Its ability to combat microorganisms can be harnessed to create new solutions for various industries, including healthcare and sanitation.
However, it is essential to handle 3-Bromo-5-nitrotoluene with care, as it is toxic and may cause irritation to the skin, eyes, and respiratory system. Proper safety measures should be taken to minimize any adverse effects during its use in various applications.

InChI:InChI=1/C7H6BrNO2/c1-5-2-6(8)4-7(3-5)9(10)11/h2-4H,1H3

Upstream product

• 500728-37-0 1-bromo-2-iodo-5-methyl-3-nitrobenzene 
• 827-24-7 2-bromo-4-methyl-6-nitroaniline 
• 102170-56-9 2-bromo-6-methyl-4-nitroaniline 
• 614-83-5 2-bromo-4-methylacetanilide 
• 99-52-5 2-methyl-4-nitro-benzenamine 
• 27329-27-7 4-methyl-2-nitrobenzoic acid 
• 849062-36-8 (3-bromo-5-methylphenyl)boronic acid 
• 942069-53-6 2-(3-bromo-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 591-17-3 meta-bromotoluene 
• 77811-44-0 4-bromo-2-methyl-6-nitroaniline 
• 6303-21-5 hypophosphorous acid 
• 618-85-9 3,5-dinitrotoluene 
• 89-62-3 4-methyl-2-nitroaniline 
• 139291-81-9 2-methyl-4-nitroaniline hydrochloride 

Downstream Products

• 74586-53-1 3-bromo-5-methylaniline 
• 97378-75-1 bis-(3-bromo-5-methyl-phenyl)-diazene 
• 124289-26-5 α-Bromo-3-cyano-5-nitrotoluene 
• 124289-28-7 α,α-Dibromo-3-cyano-5-nitrotoluene 
• 594862-57-4 6-bromohexyl 4-(3-methyl-5-nitrophenyl)but-3-ynyl ether 
• 1044209-87-1 tert-butyl 4-(3-methyl-5-nitrophenyl)piperazine-1-carboxylate 
• 594862-17-6 (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-(6-{[4-(3-methyl-5-nitrophenyl)-3-butyn-1-yl]oxy}hexyl)-1,3-oxazolidin-2-one 
• 1239596-48-5 1-methyl-5-(3-methyl-5-nitrophenyl)-1H-tetrazole 
• 1335496-82-6 3-methyl-5-morpholinoaniline 
• 1335496-66-6 4-(3-methyl-5-nitrophenyl)morpholine 

Relevant academic research and scientific papers

Ipso Nitration of Aryl Boronic Acids Using Fuming Nitric Acid

The ipso nitration of aryl boronic acid derivatives has been developed using fuming nitric acid as the nitrating agent. This facile procedure provides efficient and chemoselective access to a variety of aromatic nitro compounds. While several activating agents and nitro sources have been reported in the literature for this synthetically useful transformation, this report demonstrates that these processes likely generate a common active reagent, anhydrous HNO3. Kinetic and mechanistic studies have revealed that the reaction order in HNO3 is >2 and indicate that the ?NO2 radical is the active species.

Structure-based design of highly selective 2,4,5-trisubstituted pyrimidine CDK9 inhibitors as anti-cancer agents

Cyclin-dependent kinases (CDKs) are a family of Ser/Thr kinases involved in cell cycle and transcriptional regulation. CDK9 regulates transcriptional elongation and this unique property has made it a potential target for several diseases. Due to the conserved ATP binding site, designing selective CDK9 inhibitors has been challenging. Here we report our continued efforts in the optimization of 2,4,5-tri-substituted pyrimidine compounds as potent and selective CDK9 inhibitors. The most selective compound 30m was >100-fold selective for CDK9 over CDK1 and CDK2. These compounds showed broad anti-proliferative activities in various solid tumour cell lines and patient-derived chronic lymphocytic leukaemia (CLL) cells. Decreased phosphorylation of the carboxyl terminal domain (CTD) of RNAPII at Ser-2 and down-regulation of anti-apoptotic protein Mcl-1 were confirmed in both the ovarian cancer model A2780 and patient-derived CLL cells.

meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation

Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.

Pd-Catalyzed Decarboxylative Ortho-Halogenation of Aryl Carboxylic Acids with Sodium Halide NaX Using Carboxyl as a Traceless Directing Group

A highly regioselective Pd-catalyzed carboxyl directed decarboxylative ortho-C-H halogenation of cheap o-nitrobenzoic acids with NaX (X = I, Br) under aerobic conditions has been established. The utility of the method has been demonstrated by the gram-scale reaction and derivatization of the product. Experimental results have confirmed Pd and Bi played critical roles in the transformation and indicated the transformation might proceed via 2-halo-6-nitrobenzoic acid derivative intermediate.

Design, synthesis and structure–activity relationships of novel phenylalanine-based amino acids as kainate receptors ligands

A new series of carboxyaryl-substituted phenylalanines was designed, synthesized and pharmacologically characterized in vitro at native rat ionotropic glutamate receptors as well as at cloned homomeric kainate receptors GluK1–GluK3. Among them, six compounds bound to GluK1 receptor subtypes with reasonable affinity (Kivalues in the range of 4.9–7.5?μM). A structure–activity relationship (SAR) for the obtained series, focused mainly on the pharmacological effect of structural modifications in the 4- and 5-position of the phenylalanine ring, was established. To illustrate the results, molecular docking of the synthesized series to the X-ray structure of GluK1 ligand binding core was performed. The influence of individual substituents at the phenylalanine ring for both the affinity and selectivity at AMPA, GluK1 and GluK3 receptors was analyzed, giving directions for future studies.

The discovery of long-acting saligenin β2 adrenergic receptor agonists incorporating a urea group

A series of novel, potent and selective human β2 adrenoceptor agonists incorporating a urea moiety on the terminal right-hand side phenyl ring of (R)-salmeterol is presented. Urea 9j had long duration of action in vitro on guinea pig trachea, and also in vivo similar to that of salmeterol. It had lower oral absorption and bioavailability than salmeterol in both rat and dog. It had a turnover ratio similar to salmeterol, with no evidence for formation of any aniline metabolites in human liver microsomes and hepatocytes. However no crystalline salts suitable for inhaled delivery were identified.

PHENETHANOLAMINE DERIVATIVES FOR TREATMENT OF RESPIRATORY DISEASES

The present invention relates to novel compounds of formula (I),to a process for their manufacture, to pharmaceutical compositions containing them, and to their use in therapy, in particular their use in the prophylaxis and treatment of respiratory diseases.

2-IMIDAZOLINE, 2-OXAZOLINE, 2-THIAZOLINE, AND 4-IMIDAZOLE DERIVATIVES OF METHYLPHENYL, METHOXYPHENYL, AND AMINOPHENYL ALKYLSULFONAMIDES AND UREAS AND THEIR USE

The present invention concerns novel compounds represented by the Formula: STR1 wherein: A is R 1 q (R 3 R 60 N). sub.m (Z)(NR 2) n ; m and q are each 0 or 1, with the proviso that when q is 1, m is 0 and when q is 0, m is 1; Z is C=O or SO 2 ; n is 1 with the proviso that, when Z is C=O, m is 1; X is--NH--,--CH 2--, or--OCH 2--; Y is 2-imidazoline, 2-oxazoline, 2-thiazoline, or 4-imidazole; R 1 is H, lower alkyl, or phenyl, with the proviso that, when R 1 is H, m is 1; R 2, R 3, R 60 are each independently H, lower alkyl, or phenyl; R 4, R 5, R. sup.6, and R 7 are each independently hydrogen, lower alkyl,--CF. sub.3, lower alkoxy, halogen, phenyl, lower alkeny, hydroxyl, lower alkylsulfonamido, or lower cycloalkyl, wherein R. sup.2 and R 7 optionally may be taken together to form alkylene or alkenylene of 2 to 3 atoms in an unsubstituted or optionally substituted 5-or 6-membered ring, wherein the optional substituents on the ring are halo, lower alkyl, or--CN, with the proviso that, when R 7 is hydroxyl or lower alkylsulfonamido, then X is not--NH--when Y is 2-imidazoline. The compounds include pharmaceutically acceptable salts of the above. In the above formula A may be, for example, (R 1 SO 2 NR 2--), (R. sup.3 R 60 NSO 2 NR 2--), or (R 3 R 60 NCONR 2--). The invention also includes the use of the above compounds, and compositions containing them, as alpha 1A/1L agonists in the treatment of various disease states such as urinary incontinence, nasal congestion, priapism, depression, anxiety, dementia, senility, Alzheimer's, deficiencies in attentiveness and cognition, and eating disorders such as obesity, bulimia, and anorexia.

Phenyl-and aminophenyl-alkylsulfonamide and urea derivatives, their preparation and their use as alpha1A/1L adrenoceptor agonists

The present invention concerns novel compounds represented by the Formula:*(formula 02)* wherein: A is R1q(R3R60N)m(Z)(NR2)n; m and q are each 0 or 1, with the proviso that when q is 1, m is 0 and when q is 0, m is 1; Z is C=O or SO 2; n is 1 with the proviso that, when Z is C=O, m is 1; X is -NH-, -CH2-, or -OCH2-; Y is 2-imidazoline, 2-oxazoline, 2-thiazoline, or 4-imidazole; R 1 is H, lower alkyl, or phenyl, with the proviso that, when R1 is H, m is 1; R2, R3, R60 are each independently H, lower alkyl, or phenyl; R4, R5, R6, and R7 are each independently hydrogen, lower alkyl, - CF 3, lower alkoxy, halogen, phenyl, lower alkeny, hydroxyl, lower alkylsulfonamido, or lower cycloalkyl, wherein R2 and R7 optionally may be taken together to form alkylene or alkenylene of 2 to 3 atoms in an unsubstituted or optionally substituted 5-or 6-membered ring, wherein the optional substituents on the ring are halo, lower alkyl, or -CN,with the proviso that, when R7 is hydroxyl or lower alkylsulfonamido, then X is not -NH- when Y is 2-imidazoline. The compounds include pharmaceutically acceptable salts of the above. In the above formula A may be, for example, (R1SO2NR2-), (R3R60NSO2NR2-), or (R3R60NCONR2-). The invention also includes the use of the above compounds, and compositions containing them, as alpha 1A/1L agonists in the treatment of various disease states such as urinary incontinence, nasal congestion, priapism, depression, anxiety, dementia, senility, Alzheimer's, deficiencies in attentiveness and cognition, and eating disorders such as obesity, bulimia, and anorexia.

Synthesis, antimalarial activity, and molecular modeling of tebuquine analogues

Tebuquine (5) is a 4-aminoquinoline that is significantly more active than amodiaquine (2) and chloroquine (1) both in vitro and in vive. We have developed a novel more efficient synthetic route to tebuquine analogues which involves the use of a palladium-catalyzed Suzuki reaction to introduce the 4- chlorophenyl moiety into the 4-hydrexyaniline side chain. Using similar methodology, novel synthetic routes to fluorinated (7a,b) and a dehydroxylated (7c) analogue of tebuquine have also been developed. The novel analogues were subjected to testing against the chloroquine sensitive HB3 strain and the chloroquine resistant K1 strain of Plasmodium falciparum. Tebuquine was the most active compound tested against both strains of Plasmodia. Replacement of the 4-hydroxy function with either fluorine or hydrogen led to a decrease in antimalarial activity. Molecular modeling of the tebuquine analogues alongside amodiaquine and chloroquine reveals that the inter-nitrogen separation in this class of drugs ranges between 9.36 and 9.86 ? in their isolated diprotonated form and between 7.52 and 10.21 ? in the heme-drug complex. Further modeling studies on the interaction of 4- aminoquinolines with the proposed cellular receptor heme revealed favorable interaction energies for chloroquine, amodiaquine, and tebuquine analogues. Tebuquine, the most potent antimalarial in the series, had the most favorable interaction energy calculated in both the in vacuo and solvent-based simulation studies. Although fluorotebuquine (7a) had a similar interaction energy to tebuquine, this compound had significantly reduced potency when compared with (5). This disparity is possibly the result of the reduced cellular accumulation (CAR) of fluorotebuquine when compared with tebuquine within the parasite. Measurement of the cellular accumulation of the tebuquine analogues and seven related 4-aminoquinolines shows a significant relationship (r = 0.98) between the CAR of 4-aminoquinoline drugs and the reciprocal of drug IC50.