20776-50-5

Basic information

• Product Name: 2-Amino-4-bromobenzoic acid
• Synonyms: BENZOIC ACID, 2-AMINO-4-BROMO-;BUTTPARK 49\07-49;4-bromo-2-aminoebnzoic acid;2-azanyl-4-bromo-benzoic acid;2-Amino-4-bromobenzoic acid ,98%;5-Bromo-2-carboxyaniline, 4-Bromoanthranilic acid;2 - aMino - 4 - broMine benzoic acid;2-Amino-4-bromobenzoic acid 97%
• CAS NO: 20776-50-5
• Molecular Formula: C₇H₆BrNO₂
• Molecular Weight: 216.03
• EINECS: 244-025-7
• Product Categories: benzene derivative;Multisubstituted Benzene;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Carboxylic Acids;Phenyls & Phenyl-Het;Carboxylic Acids;Phenyls & Phenyl-Het;Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives;Benzoic acid series;Pyrrolidines
• Mol File: 20776-50-5.mol
• Article Data: 26

Chemical Properties

• Melting Point: 230-234 °C
• Boiling Point: 352.4 °C at 760 mmHg
• Flash Point: 166.9 °C
• Appearance: slight yellow to white powder
• Density: 1.793 g/cm³
• Vapor Pressure: 1.43E-05mmHg at 25°C
• Refractive Index: 1.672
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.71±0.10(Predicted)
• Water Solubility: Soluble in water (slightly).
• CAS DataBase Reference: 2-Amino-4-bromobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-bromobenzoic acid(20776-50-5)
• EPA Substance Registry System: 2-Amino-4-bromobenzoic acid(20776-50-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 20776-50-5(Hazardous Substances Data)

Usage

Description

2-Amino-4-bromobenzoic acid is an organic compound characterized by its slight yellow to white powder appearance. It is a significant building block and intermediate in various chemical syntheses, particularly in the fields of pharmaceuticals, agrochemicals, and dyestuff.

Uses

Used in Organic Synthesis:
2-Amino-4-bromobenzoic acid is used as a key intermediate for the synthesis of various organic compounds due to its reactive functional groups, which can be further modified to produce a wide range of products.
Used in Pharmaceutical Industry:
2-Amino-4-bromobenzoic acid is used as an important raw material in the development of pharmaceuticals. Its unique structure allows it to be incorporated into the design of new drugs, potentially leading to novel therapeutic agents.
Used in Agrochemicals:
In the agrochemical industry, 2-Amino-4-bromobenzoic acid is utilized as a starting material for the synthesis of various agrochemical products, such as pesticides and herbicides, which are essential for crop protection and increased agricultural productivity.
Used in Dyestuff Industry:
2-Amino-4-bromobenzoic acid is also employed in the dyestuff industry as a crucial intermediate for the production of various dyes and pigments. Its chemical properties make it suitable for creating a diverse array of colorants used in different applications, such as textiles, plastics, and printing inks.

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

Upstream product

• 101861-53-4 2-(methylcarbonylamino)-4-bromobenzoic acid 
• 116436-10-3 5’-bromo-2’-methylacetanilide 
• 65971-74-6 N-(3-bromophenyl)-2-(hydroxyimino)ethanamide 
• 591-19-5 m-Bromoaniline 
• 135484-83-2 2-amino-4-bromo-benzoic acid methyl ester 
• 19201-53-7 6,6′?di?bromo?indigo 
• 6941-75-9 5-Bromoisoindoline-1,3-dione 
• 611-00-7 2,4-dibromobenzoic acid 
• 117323-99-6 ethyl 2-amino-4-bromobenzoate 
• 106-38-7 para-bromotoluene 
• 39478-78-9 5-bromo-2-methylaniline 
• 60956-26-5 4-bromo-2-nitrotoluene 
• 79603-03-5 4-bromo-2-nitro-benzonitrile 
• 875-51-4 4-Bromo-2-nitroaniline 

Downstream Products

• 135484-83-2 2-amino-4-bromo-benzoic acid methyl ester 
• 861526-61-6 4-bromo-2-(methylamino)benzoic acid 
• 58483-71-9 2-benzothiazol-2-ylamino-4-bromo-benzoic acid 
• 58483-73-1 4-bromo-2-(6-chloro-benzothiazol-2-ylamino)-benzoic acid 
• 58483-76-4 4-bromo-2-(6-nitro-benzothiazol-2-ylamino)-benzoic acid 
• 872091-24-2 N-[3-(7-bromo-4-oxo-4H-quinazolin-3-yl)-4-methylphenyl]-3-(1-cyano-1-methylethyl)benzamide 
• 1204536-73-1 2-Amino-7-(4-aminophenyl)-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid Amide 
• 1357259-11-0 C₂₀H₂₀BrN₃O₄ 
• 1357259-12-1 C₂₀H₁₈BrN₃O₃ 
• 1357259-14-3 C₄₂H₄₂N₆O₅ 
• 1357259-18-7 C₄₄H₄₅N₇O₆ 
• 1357258-58-2 C₄₉H₅₄N₈O₇ 
• 1357258-59-3 C₄₆H₄₈N₈O₇ 
• 1357258-60-6 C₅₀H₅₄N₈O₇ 

Relevant articles and documents

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Selenium-catalyzed intramolecular atom- And redox-economical transformation ofo-nitrotoluenes into anthranilic acids

Anthranilic acids (AAs) are significant basic chemicals used in pharmaceuticals, agrochemicals, dyes, fragrances,etc. Superfluous steps are always involved in obtaining AAs. Herein, we demonstrate a straightforward strategy to transform abundanto-nitrotoluenes into biologically and pharmaceutically significant AAs without any extra reductants, oxidants and protecting groups. Various sensitive groups, such as halogens, sulfide, aldehyde, pyridines, quinolines,etc., can be tolerated in this transformation. A hundred-gram-scale operation is realized efficiently with almost quantitative selenium recycling. Further mechanistic studies and DFT calculations disclosed the proposed atom-exchange processes and the key roles of the selenium species.

Discovery of Novel Tacrine-Pyrimidone Hybrids as Potent Dual AChE/GSK-3 Inhibitors for the Treatment of Alzheimer's Disease

Based on a multitarget strategy, a series of novel tacrine-pyrimidone hybrids were identified for the potential treatment of Alzheimer's disease (AD). Biological evaluation results demonstrated that these hybrids exhibited significant inhibitory activities toward acetylcholinesterase (AChE) and glycogen synthase kinase 3 (GSK-3). The optimal compound 27g possessed excellent dual AChE/GSK-3 inhibition both in terms of potency and equilibrium (AChE: IC50 = 51.1 nM; GSK-3β: IC50 = 89.3 nM) and displayed significant amelioration on cognitive deficits in scopolamine-induced amnesia mice and efficient reduction against phosphorylation of tau protein on Ser-199 and Ser-396 sites in glyceraldehyde (GA)-stimulated differentiated SH-SY5Y cells. Furthermore, compound 27g exhibited eligible pharmacokinetic properties, good kinase selectivity, and moderate neuroprotection against GA-induced reduction in cell viability and neurite damage in SH-SY5Y-derived neurons. The multifunctional profiles of compound 27g suggest that it deserves further investigation as a promising lead for the prospective treatment of AD.

A Facile Access to Primary Alkylamines and Anilines via Ir(III)-Catalyzed C-H Amidation Using Azidoformates

Described herein is the development of Ir(III)-catalyzed direct C-H amidation using azidoformates as a readily deprotectable amino source. Substrates with unactivated methyl C(sp3)-H and aromatic or olefinic C(sp2)-H bonds were smoothly reacted by the iridium-based catalyst system to provide the corresponding primary alkylamines and anilines upon the subsequent removal of N-protecting groups, such as Boc, Fmoc, Cbz, pNZ, or Troc. A brief mechanistic study and synthetic applications are also presented.