570-23-0

Basic information

• Product Name: 3-Aminosalicylic acid
• Synonyms: Benzoic acid, 3-amino-2-hydroxy-;Salicylic acid, 3-amino-;TIMTEC-BB SBB001895;3-AMINOSALICYLIC ACID;3-AMINO-2-HYDROXYBENZOIC ACID;3-Amino-2-hydroxybenzoic acid 97%;3-AMINO-2-HYDROXYBENZOIC ACID / 3-AMINOSALICYLIC ACID;3-AMINOSALICYLIC ACID 98%
• CAS NO: 570-23-0
• Molecular Formula: C₇H₇NO₃
• Molecular Weight: 153.14
• EINECS: 209-328-0
• Product Categories: Intermediates of Dyes and Pigments;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Carboxylic Acids;Phenyls & Phenyl-Het;Organic acids;Carboxylic Acids;Phenyls & Phenyl-Het
• Mol File: 570-23-0.mol

Chemical Properties

• Melting Point: 240 °C (dec.)(lit.)
• Boiling Point: 276.03°C (rough estimate)
• Flash Point: 162.108 °C
• Appearance: tan to brown/Powder
• Density: 1.3585 (rough estimate)
• Vapor Pressure: 2.51E-05mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 2.13±0.10(Predicted)
• Water Solubility: Slightly soluble in water
• Stability: Hygroscopic
• BRN: 2090427
• CAS DataBase Reference: 3-Aminosalicylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Aminosalicylic acid(570-23-0)
• EPA Substance Registry System: 3-Aminosalicylic acid(570-23-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 570-23-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Aminosalicylic acid is used as an active pharmaceutical ingredient (API) for the treatment of inflammatory bowel diseases (IBD), such as Crohn's disease and ulcerative colitis. It is incorporated into drugs like mesalazine and sulfasalazine, which help reduce inflammation and alleviate symptoms in IBD patients.
Used in Coordination Chemistry:
3-Aminosalicylic acid acts as an oxygen, nitrogen donor ligand and forms complexes with silver. These complexes have potential applications in various fields, such as catalysis, materials science, and medicinal chemistry.
Used in Organic Synthesis:
3-Aminosalicylic acid is a building block that can be used to synthesize various organic compounds, such as antimycin A3, which is a potent antibiotic and antitumor agent. It can also be used to synthesize 2-alkoxy-3-(arylaminomethylene)chroman-4-ones and 3-(aryliminomethyl)chromones by reacting with 3-formylchromones. These synthesized compounds have potential applications in pharmaceuticals, agrochemicals, and other industries.

InChI:InChI=1/C7H7NO3/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,9H,8H2,(H,10,11)/p-1

Upstream product

• 15719-64-9 methylammonium carbonate 
• 95-55-6 2-amino-phenol 
• 124-38-9 carbon dioxide 
• 7195-78-0 5-chloro-2-hydroxy-3-nitrobenzoic acid 
• 321-14-2 5-chloro-2-hydroxybenzoic acid 
• 10169-50-3 5-bromo-2-hydroxy-3-nitrobenzoic acid 
• 35748-34-6 methyl 3-aminosalicylate 
• 298-14-6 potassium hydrogencarbonate 
• 69-72-7 salicylic acid 
• 85-38-1 3-nitrosalicylic acid 
• 64-19-7 acetic acid 
• 642-82-0 antimycinic acid 

Downstream Products

• 17968-71-7 2-hydroxy-3-formylaminobenzoic acid 
• 1234847-45-0 ethyl 2-methylbenzoxazole-7-carboxylate 
• 1338065-60-3 N-(4-(trifluoromethyl)-2-(piperidin-1-yl)benzyl)-3-amino-2-hydroxybenzamide 
• 52395-92-3 2-methyl-benzoxazole-7-carboxylic acid 
• 520-79-6 2-hydroxy-3-iodobenzoic acid 
• 528607-19-4 2-(4-Isobutoxy-3-nitrophenyl)benzoxazole-7-carboxylic acid 
• 213685-86-0 6-((7-aminobenzo[d]oxazol-2-yl)thio)-N-(2,6-diisopropylphenyl)hexanamide 
• 213685-85-9 t-butyl (2-((6-((N-2,6-diisopropylphenyl)amino)-6-oxohexyl)thio)benzo[d]oxazol-7-yl)carbamate 
• 213685-05-3 N-(2,6-diisopropylphenyl)-6-((7-((N,N-dimethylamino)methyl)benzo[d]oxazol-2-yl)thio)hexanamide 
• 213685-04-2 N-(2,6-diisopropylphenyl)-6-((7-(hydroxymethyl)benzo[d]oxazol-2-yl)thio)hexanamide 
• 213685-03-1 2-((6-((2,6-diisopropylphenyl)amino)-6-oxohexyl)thio)benzo[d]oxazole-7-carboxylic acid 

Relevant articles and documents

Functional Group-Directed Photochemical Reactions of Aromatic Alcohols, Amines, and Thiols Triggered by Excited-State Hydrogen Detachment: Additive-free Oligomerization, Disulfidation, and C(sp2)-H Carboxylation with CO2

Exploring new types of photochemical reactions is of great interest in the field of synthetic chemistry. Although excited-state hydrogen detachment (ESHD) represents a promising prospective template for additive-free photochemical reactions, applications of ESHD in a synthetic context remains scarce. Herein, we demonstrate the expansion of this photochemical reaction toward oligomerization, disulfidation, and regioselective C(sp2)-H carboxylation of aromatic alcohols, thiols, and amines. In the absence of any radical initiators in tetrahydrofuran upon irradiation with UV light (λ = 280 or 300 nm) under an atmosphere of N2 or CO2, thiols and catechol afforded disulfides and oligomers, respectively, as main products. Especially, the photochemical disulfidation proceeded highly selectively with the NMR and quantum yields of up to 69 and 0.46%, respectively. In stark contrast, the photolysis of phenylenediamines and aminophenols results in photocarboxylation in the presence of CO2 (1 atm). p-Aminophenol was quantitatively carboxylated by photolysis for 17 h with a quantum yield of 0.45%. Furthermore, the photocarboxylation of phenylenediamines and aminophenols proceeds in a highly selective fashion on the aromatic C(sp2)-H bond next to a functional group, which is directed by the site-selective ESHD of the functional groups for the formation of aminyl and hydroxyl radicals.

3-process for the preparation of amino-salicylic acid

The invention relates to a novel preparation method of 3-aminosalicylic acid. The novel preparation method is characterized in that a salicylic acid compound I as an initial raw material having a general formula shown in the description and a nitration agent undergo a reaction to produce a 3-nitrosalicylic acid compound II having a general formula shown in the description, and the 3-nitrosalicylic acid compound II undergoes nitryl catalytic hydrogenation reduction and dehalogenation hydrogenolysis reactions in the presence of an effective dose of a catalyst and hydrogen donors so that 3-aminosalicylic acid is produced.

Selective Functionalization of Antimycin A Through an N-Transacylation Reaction

Acylation of 3-(N-formylamino)salicylic acids resulted in transacylation with loss of the formyl moiety. The reaction proceeds through a bis-N-acylated intermediate, which undergoes facile deformylation. This transacylation reaction has been employed for the site-specific functionalization of the mitochondrial poison antimycin A, affording several novel derivatives. The selective cytotoxicity of some of these derivatives toward cultured A549 human lung epithelial adenocarcinoma cells, in comparison with WI-38 normal human lung fibroblasts, illustrates one application of this transacylation reaction.

Evaluation of the Synthetic Potential of an AHBA Knockout Mutant of the Rifamycin Producer Amycolatopsis mediterranei

Supplementing an AHBA(-) mutant strain of Amycolatopsis mediterranei, the rifamycin producer, with a series of benzoic acid derivatives yielded new tetraketides containing different phenyl groups. These mutasynthetic studies revealed unique reductive properties of A. mediterranei towards nitro- and azidoarenes, leading to the corresponding anilines. In selected cases, the yields of mutaproducts (fermentation products isolated after feeding bacteria with chemically prepared analogs of natural building blocks) obtained are in a range (up to 118 mg L-1) that renders them useful as chiral building blocks for further synthetic endeavors. The configuration of the stereogenic centers at C6 and C7 was determined to be 6R,7S for one representative tetraketide. Importantly, processing beyond the tetraketide stage is not always blocked when the formation of the bicyclic naphthalene precursor cannot occur. This was proven by formation of a bromo undecaketide, an observation that has implications regarding the evolutionary development of rifamycin biosynthesis.

Regioselective ortho-carboxylation of phenols catalyzed by benzoic acid decarboxylases: A biocatalytic equivalent to the Kolbe-Schmitt reaction

The enzyme catalyzed carboxylation of electron-rich phenol derivatives employing recombinant benzoic acid decarboxylases at the expense of bicarbonate as CO2 source is reported. In contrast to the classic Kolbe-Schmitt reaction, the biocatalytic equivalent proceeded in a highly regioselective fashion exclusively at the ortho-position of the phenolic directing group in up to 80% conversion. Several enzymes were identified, which displayed a remarkably broad substrate scope encompassing alkyl, alkoxy, halo and amino- functionalities. Based on the crystal structure and molecular docking simulations, a mechanistic proposal for 2,6-dihydroxybenzoic acid decarboxylase is presented.

BICYCLIC RING SYSTEM SUBSTITUTED AMIDE FUNCTIONALISED PHENOLS AS MEDICAMENTS

This invention relates to bicyclic ring system substituted amide functionalized phenols of general formula 1, their use as inhibitors of CXCR2 activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of respiratory or gastrointestinal complaints or diseases, inflammatory diseases of the joints, skin, or eyes, diseases of the peripheral or central nervous system or cancers, as well as pharmaceutical compositions which contain these compounds.

BICYCLIC RING SYSTEM SUBSTITUTED AMIDE FUNCTIONALISED PHENOLS AS MEDICAMENTS

This invention relates to bicyclic ring system substituted amide functionalized phenols of general formula 1, their use as inhibitors of CXCR2 activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of respiratory or gastrointestinal complaints or diseases, inflammatory diseases of the joints, skin, or eyes, diseases of the peripheral or central nervous system or cancers, as well as pharmaceutical compositions which contain these compounds

Synthesis and characterization of ruthenium(III) chloride complexes with some 1,2-disubstituted benzimidazoles and their catalytic activity

Reaction of ruthenium(III) chloride with 2-mono substituted and 1,2-disubstituted benzimidazoles yield the complexes of the formulae RuCl 3Ly.nH2O [L = 2-o-hydroxyphenylbenzimidazole (oHPB), y = 3, n = 0; L = 2-p-hydroxyphenylbenzimidazole (pHPB), y = 2, n = 3], and RuCl3L2.H2O [L = 1-o-hydroxybenzyl-2-o-hydroxyphenylbenzimidazole (oHBPB), 1-m-hydroxybenzyl-2-m-hydroxyphenylbenzimidazole (mHBPB), and 1-p-hydroxybenzyl-2-p-hydroxyphenylbenzimidazole (pHBPB)]. The complexes are characterized by elemental analysis, conductivity measurements, infrared, electronic, 1H- and 13C-NMR spectral studies, as well as by thermal analysis. The complexes exhibit octahedral geometry. Some of the complexes act as potential catalyst towards transferhydrogenation. Copyright Taylor & Francis Group, LLC.