7459-95-2

Basic information

• Product Name: anthranilic acid dihydrochloride
• Synonyms: anthranilic acid dihydrochloride;Benzoic acid, 2-amino-, dihydrochloride;Benzoic acid, 2-amino-, hydrochloride (1:2);Einecs 231-241-1
• CAS NO: 7459-95-2
• Molecular Formula: C7H9Cl2NO2
• Molecular Weight: 210.05786
• EINECS: 231-241-1
• Mol File: 7459-95-2.mol

Chemical Properties

• Boiling Point: 311.9°Cat760mmHg
• Flash Point: 142.4°C
• Appearance: /
• Density: 1.315g/cm³
• Vapor Pressure: 0.000234mmHg at 25°C
• CAS DataBase Reference: anthranilic acid dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: anthranilic acid dihydrochloride(7459-95-2)
• EPA Substance Registry System: anthranilic acid dihydrochloride(7459-95-2)

Safety Data

• Hazardous Substances Data: 7459-95-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H7NO2.2ClH/c8-6-4-2-1-3-5(6)7(9)10;;/h1-4H,8H2,(H,9,10);2*1H

Upstream product

• 552-16-9 ortho-nitrobenzoic acid 
• 861402-58-6 2-[(2-oxobutanoyl)amino]benzoic acid 
• 3342-77-6 N-formylanthranilic acid 
• 118-92-3 anthranilic acid 

Downstream Products

• 4478-04-0 2-(3-phenyl-triazenyl)-benzoic acid 
• 90557-83-8 N-glycyl-anthranilic acid 
• 29029-50-3 3-(4-chloro-phenyl)-2-phenyl-thiazolo[2,3-b]quinazolin-5-one 
• 29416-94-2 2,3-bis-(4-methoxy-phenyl)-thiazolo[2,3-b]quinazolin-5-one 
• 23961-11-7 N-phenylalanyl-anthranilic acid 
• 29029-46-7 2,3-diphenyl-thiazolo[2,3-b]quinazolin-5-one 
• 94330-85-5 1-(4-ethyl-phenyl)-thiazolo[3,2-a]quinazolin-5-one 
• 1637-61-2 1-(4-bromo-phenyl)-3H-[1,3]thiazino[3,2-a]quinazolin-6-one 
• 94540-24-6 1-(4-chloro-phenyl)-2-methyl-thiazolo[3,2-a]quinazolin-5-one 
• 93261-54-2 1-(4-bromo-phenyl)-2-methyl-thiazolo[3,2-a]quinazolin-5-one 
• 93326-88-6 1-(2-hydroxy-5-methoxy-phenyl)-thiazolo[3,2-a]quinazolin-5-one 
• 77200-74-9 C₂₁H₁₄N₈O₆ 
• 80837-76-9 C₃₁H₂₄N₂O₅ 
• 81743-89-7 2-(4-fluorophenyl)benzo[d][1,2] selenazol-3(2H)-one 

Relevant articles and documents

Identification of methionine aminopeptidase 2 as a molecular target of the organoselenium drug ebselen and its derivatives/analogues: Synthesis, inhibitory activity and molecular modeling study

A collection of twenty-six organoselenium compounds, ebselen and its structural analogues, provided a novel approach for inhibiting the activity of human methionine aminopeptidase 2 (MetAP2). This metalloprotease, being responsible for the removal of the amino-terminal methionine from newly synthesized proteins, plays a key role in angiogenesis, which is essential for the progression of diseases, including solid tumor cancers. In this work, we discovered that ebselen, a synthetic organoselenium drug molecule with anti-inflammatory, anti-oxidant and cytoprotective activity, inhibits one of the main enzymes in the tumor progression pathway. Using three-step synthesis, we obtained twenty-five ebselen derivatives/analogues, ten of which are new, and tested their inhibitory activity toward three neutral aminopeptidases (MetAP2, alanine and leucine aminopeptidases). All of the tested compounds proved to be selective, slow-binding inhibitors of MetAP2. Similarly to ebselen, most of its analogues exhibited a moderate potency (IC50= 1–12 μM). Moreover, we identified three strong inhibitors that bind favorably to the enzyme with the half maximal inhibitory concentration in the submicromolar range.

The ortho effect on the acidic and alkaline hydrolysis of substituted formanilides

The kinetics of formanilides hydrolysis were determined under first-order conditions in hydrochloric acid (0.01-8 M, 20-60°C) and in hydroxide solutions (0.01-3 M, 25 and 40°C). Under acidic conditions, second-order specific acid catalytic constants were used to construct Hammett plots. The ortho effect was analyzed using the Fujita-Nishioka method. In alkaline solutions, hydrolysis displayed both first- and second-order dependence in the hydroxide concentration. The specific base catalytic constants were used to construct Hammett plots. Ortho effects were evaluated for the first-order dependence on the hydroxide concentration. Formanilide hydrolyzes in acidic solutions by specific acid catalysis, and the kinetic study results were consistent with the AAC2 mechanism. Ortho substitution led to a decrease in the rates of reaction due to steric inhibition of resonance, retardation due to steric bulk, and through space interactions. The primary hydrolytic pathway in alkaline solutions was consistent with a modified BAC2 mechanism. The Hammett plots for hydrolysis of meta- and para-substituted formanilides in 0.10 M sodium hydroxide solutions did not show substituent effects; however, ortho substitution led to a decrease in rate constants proportional to the steric bulk of the substituent.

Spectroscopic studies on gallic acid and its azo derivatives and their iron(III) complexes

Azo gallic derivatives and their iron(III) complexes were synthesized and characterized. The stereochemistry and the mode of bonding of the complexes were achieved based on elemental analysis, UV-Vis and IR. The thermal behaviors of the complexes were studied. The effect of pH on the electronic absorption spectra of gallic acid and its azo derivatives are discussed. Different spectroscopic methods (molar ratio, straight line method, continuous variation, slope ratio and successive method) are applied for determination of stoichiometry and pK values for the complex formation of gallic acid with iron(III) in aqueous media. Iron(III) complexes of gallic acid is formed with different ratio: 1:1, 1:2, 1:3 and 1:4 (M:L).

Oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones into N-(α-ketoacyl)anthranilic acids Dedicated to Professor Slovenko Polanc on his 65th birthday

N-(α-Ketoacyl)anthranilic acids were prepared by oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones by using paraperiodic acid (H5IO6) or sodium periodate (NaIO4). The optimisation of the reaction conditions is