80074-26-6

Basic information

• Product Name: 5-[(2-chloroacetyl)amino]-2-hydroxy-benzoic acid
• Synonyms: 5-[(Chloroacetyl)amino]-2-hydroxybenzoic acid;5-(2-chloroethanoylamino)-2-hydroxy-benzoic acid;5-[(2-chloro-1-oxoethyl)amino]-2-hydroxybenzoic acid;NSC17829
• CAS NO: 80074-26-6
• Molecular Formula: C₉H₈ClNO₄
• Molecular Weight: 229.62
• Mol File: 80074-26-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 507.5°C at 760 mmHg
• Flash Point: 260.7°C
• Appearance: /
• Density: 1.585g/cm³
• Vapor Pressure: 4.03E-11mmHg at 25°C
• Refractive Index: 1.671
• CAS DataBase Reference: 5-[(2-chloroacetyl)amino]-2-hydroxy-benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[(2-chloroacetyl)amino]-2-hydroxy-benzoic acid(80074-26-6)
• EPA Substance Registry System: 5-[(2-chloroacetyl)amino]-2-hydroxy-benzoic acid(80074-26-6)

Safety Data

• Hazardous Substances Data: 80074-26-6(Hazardous Substances Data)

Usage

General Description

5-[(2-chloroacetyl)amino]-2-hydroxy-benzoic acid is a chemical compound with the molecular formula C9H8ClNO4. It is a derivative of salicylic acid and contains a chlorine atom, an acetyl group, an amino group, and a hydroxy group. 5-[(2-chloroacetyl)amino]-2-hydroxy-benzoic acid has potential pharmaceutical properties and may be used as a building block for the synthesis of other biologically active molecules. Its structure suggests that it may have anti-inflammatory and analgesic properties, and it could be of interest in the development of new drugs for the treatment of various medical conditions. Its specific pharmacological and toxicological properties would need to be further studied to determine its potential medical applications.

InChI:InChI=1/C9H8ClNO4/c10-4-8(13)11-5-1-2-7(12)6(3-5)9(14)15/h1-3,12H,4H2,(H,11,13)(H,14,15)

Upstream product

• 89-57-6 5-Aminosalicylic Acid 
• 79-04-9 chloroacetyl chloride 
• 42753-75-3 methyl 5-amino-2-hydroxybenzoate 
• 80074-18-6 methyl 5-chloroacetamidosalicylate 

Downstream Products

• 6245-02-9 5-[(N,N-diethyl-glycyl)-amino]-2-hydroxy-benzoic acid methyl ester 
• 105477-17-6 5-[(N,N-diethyl-glycyl)-amino]-2-hydroxy-benzoic acid 

Relevant articles and documents

Synthesis and Ameliorative Effect of Isatin–Mesalamine Conjugates on Acetic Acid-induced Colitis in Rats

A series of new isatin–mesalamine conjugates (9a–g) were synthesized via conjugation of isatin (3a) and its derivatives (3b–3d, 4, 5, and 6) with mesalamine (7) by using chloroacetyl chloride as a bifunctional linker. Compounds 3a–3d were prepared by employing Sandmeyer reaction. Compounds 4, 5, and 6 were obtained from isatin (3a) via previously reported methods. The synthesized compounds were characterized by IR, mass, 1H NMR, and 13C NMR spectral techniques. Synthesized compounds (3a–d, 4, 5, 6, and 9a–g) were evaluated for in vitro antioxidant activity by DPPH assay method using ascorbic acid as standard. Hybrids 9b (IC50?=?368.6?±?3.5?μM) and 9f (IC50?=?335.1?±?2.9?μM) showed better antioxidant activity than its parent compounds such as 3a (IC50?=?556.8?±?2.9?μM), 5 (IC50?=?511.9?±?3.6?μM), and 7 (IC50?=?768.9?±?2.7?μM). Acetic acid-induced ulcerative colitis in rat model was chosen to examine the antioxidant potential of the synthesized hybrids (9b and 9f) in the amelioration of ulcerative colitis. Colonic myeloperoxidase and malondialdehyde enzymes were used as biomarkers of anti-ulcerative colitis activity. In the present study, hybrids 9b and 9f reduced the levels of colonic myeloperoxidase and malondialdehyde enzymes significantly (p??0.05) when compared with control (colitic), at a dose (0.03?mM/12.5?mg/kg b.w. p.o.) (50%) less than that of its parent moieties mesalamine (0.16?mM/25?mg/kg) and isatin (0.16?mM/25?mg/kg). Thus, the molecular hybridization was proved to be significant in enhancing the activity of hybrids 9b and 9f by reducing the dose.