6311-37-1

Usage

Uses

4-Amino-3-bromobenzoic acid is a useful research chemical.

Chemical Properties

White to light yellow crystal powder

InChI:InChI=1/C7H6BrNO2/c8-5-3-4(7(10)11)1-2-6(5)9/h1-3H,9H2,(H,10,11)

Upstream product

• 74103-28-9 3-bromo-4-acetamidobenzoic acid 
• 150-13-0 4-amino-benzoic acid 
• 10035-10-6 hydrogen bromide 
• 7722-84-1 dihydrogen peroxide 
• 106896-49-5 methyl 4-amino-3-bromobenzoate 

Downstream Products

• 194809-38-6 N-(4-amino-3-bromobenzoyl)-(αS,γR)-γ-fluoroglutamic acid α,γ-diisopropyl ester 
• 309250-39-3 8-(3-iodo-phenyl)-quinoline-6-carboxylic acid 
• 309250-42-8 8-(3-nitro-phenyl)-quinoline-6-carboxylic acid 
• 1032373-87-7 4-amino-3-bromo-N-(4-dibenzylaminophenyl)benzamide 
• 4123-72-2 4-amino-3,5-dibromobenzoic acid 
• 1344028-85-8 4-(octylamino)-3-bromobenzoic acid 
• 1344029-03-3 2-(dimethylamino)ethyl 4-(octylamino)-3-bromobenzoate 
• 1341558-98-2 (4-amino-3-bromophenyl)(morpholino)methanone 
• 106896-49-5 methyl 4-amino-3-bromobenzoate 
• 178804-06-3 2-(4-amino-3-bromophenyl)benzothiazole 

Relevant academic research and scientific papers

Green synthesis method of bromoaromatic amine and alpha-bromoaromatic ketone

The invention discloses a green synthesis method of bromoaromatic amine and alpha-bromoaromatic ketone. The synthesis method comprises: adopting hydrobromic acid as a brominating agent, adopting 2-methylpyridine nitrate as a catalyst, and adopting molecular oxygen as an oxidizing agent, brominating an aromatic compound with a structure shown in formula (1) or aromatic ketone with a structure shown in formula (2) or (3), and preparing corresponding bromoaromatic amine or alpha-bromoaromatic ketone. The synthesis method is wide in substrate application reaction, high in atom utilization rate, capable of avoiding the application of the transitional metal element and volatile organic solvent and has the characteristics of economical efficiency and environmental protection. (Shown in the description).

An efficient regioselective NBS aromatic bromination in the presence of an ionic liquid

A simple, efficient, and rapid method was developed for high-yielding regioselective monobromination of activated aromatic compounds using NBS in combination with ionic liquid 1-butyl-1-methylimidazolium bromide ([Bmim]Br) or dioxane. The ionic liquid is recyclable and can be reused with minimal loss in the catalytic efficiency if the ionic liquid is rapidly microwaved prior to reactions.

Measurement of long-range interatomic distances by solid-state tritium-NMR spectroscopy

(Chemical Equation Presented) For the structural determination of a ligand bound to an amorphous macromolecular system, solid-state NMR can be used to provide interatomic distances. It is shown here that selective labeling in discrete locations with tritium enables accurate measurement of long-range distances owing to the high gyromagnetic ratio of this nucleus, without structural modification of the molecule. This approach gives access to the largest NMR distance ever measured between two nuclei (14.4 A). 3H MAS NMR appears to be a promising tool for structural applications in the biological and material sciences. Copyright

Silica-supported quinolinium tribromide: A recoverable solid brominating reagent for regioselective monobromination of aromatic amines

Silica-supported quinolinium tribromide was synthesized and found to be an efficient, stable, and recoverable solid brominating reagent for the regioselective monobromination of aromatic amines. This protocol has advantages of high yield, mild condition and simple work-up procedure.

Non-peptidic substrate-mimetic inhibitors of Akt as potential anti-cancer agents

Akt has emerged as a critical target for the development of anti-cancer therapies. It has been found to be amplified, overexpressed, or constitutively activated in numerous human malignancies with oncogenesis derived from the simultaneous promotion of cell survival and suppression of apoptosis. A valuable alternative to the more common ATP-mimetic based chemotherapies is a substrate-mimetic approach, which has the potential advantage of inherent specificity of the substrate-binding pocket. In this paper we present the development of high affinity non-peptidic, substrate-mimetic inhibitors based on the minimum GSK3β substrate sequence. Optimization of initial peptidic leads resulted in the development of several classes of small molecule inhibitors, which have comparable potency to the initial peptidomimetics, while eliminating the remaining amino acid residues. We have identified the first non-peptidic substrate-mimetic lead inhibitors of Akt 29a-b, which have affinities of 17 and 12 μM, respectively. This strategy has potential to provide a useful set of molecular probes to assist in the validation of Akt as a potential target for anti-cancer drug design.

Effect of structural factors and solvent nature in bromination of anilines

Reaction of electrophilic bromination of aniline containing various ortho, meta, and para substituents in the aromatic ring was studied. The optimal conditions for synthesis of mono-, di-, tri-, and tetrabromo derivatives of aniline and brominated analog of Aniline Black were found.

An efficient, rapid, and regioselective bromination of anilines and phenols with 1-butyl-3-methylpyridinium tribromide as a new reagent/solvent under mild conditions

1-Butyl-3-methylpyridinium tribromide, [BMPy]Br3 proves to be a highly efficient, regioselective reagent/solvent for nuclear bromination of various anilines and phenols. The synthesis and characterization of the room temperature ionic liquid [BMPy]Br3 (2) is described. The bromination was carried out in the absence of organic solvents and in most cases the only extraction solvent needed was water. The spent 1-butyl-3-methylpyridinium bromide (1) was easily recycled.

SUBSTRATE-MIMETIC AKT INHIBITOR

Disclosed herein is a species of peptide and non-peptide inhibitors of Akt, an oncogenic protein. Beginning with 0 a residue of Akt target substrate GSK-3, the functional domains of the GSK-3 residue were characterized. Functionallv homologous non-peptide groups were substituted for the amino acids of the GSK-3 creating a hybrid peptide-non-peptide and non-peptide compounds capable of binding to Akt. The non-peptide compounds show increased stability and rigidity compared to peptide counterpartsand are less susceptible to degradation. The bound non-peptide compounds exhibit an inhibitory effect on Akt, similar to peptide-based Akt inhibitors.

Regioselective, photochemical bromination of aromatic compounds using N-bromosuccinimide

Regioselective nuclear bromination of aromatic compounds is investigated with N-bromosuccinimide as the brominating agent under UV irradiation to afford the corresponding brominated compounds. The reaction proceeds at ambient temperature (30 ± 2 °C) without any catalyst. In most of the reactions, regioselectively mono-brominated products are obtained in good to high yields. The conversion and selectivity for bromination depend on the nature of the substituent on the aromatic ring.

PRO-DRUGS OF N-THIAZOL-2YL-BENZAMIDE DERIVATIVES

The invention relates to compounds of the formula I wherein the variables are as defined in the claims. The compounds are pro-drugs of A2A-receptor ligands with improved aqueous solubility, and are useful in the treatment of neurological and psychiatric disorders where an A2A-receptor is implicated.