3479-10-5

Usage

Organic compound

2-Amino-4-chlorobenzenesulfonic acid

Chemical structure

Benzene ring with a chlorine atom and a sulfonic acid group

Uses

Manufacturing of dyes, pigments, chemicals, pharmaceuticals, agrochemicals

Physical appearance

White to off-white crystalline powder

Solubility

Soluble in water

Toxicity

Moderately toxic

Health effects

Irritation to skin, eyes, respiratory system upon contact

InChI:InChI=1/C6H6ClNO3S/c7-4-1-2-6(5(8)3-4)12(9,10)11/h1-3H,8H2,(H,9,10,11)

Upstream product

• 4153-06-4 4-chloro-2-nitrobenzenesulfenyl chloride 
• 108-42-9 3-chloro-aniline 
• 110-01-0 thiophene 
• 7664-93-9 sulfuric acid 
• 2050-66-0 bis(2-nitro-4-chlorophenyl)disulfide 
• 2786-51-8 5-chlorobenzo[d]thiazole 

Downstream Products

• 105548-06-9 4-Chloro-2-(4,6-diamino-2-ethylsulfanyl-pyrimidin-5-ylazo)-benzenesulfonic acid 
• 105547-66-8 2-(5-Amino-3-methyl-1-phenyl-1H-pyrazol-4-ylazo)-4-chloro-benzenesulfonic acid 
• 105547-87-3 2-(4-Amino-2-diethylamino-6-methyl-pyrimidin-5-ylazo)-4-chloro-benzenesulfonic acid 
• 105548-25-2 2-(2-Acetylamino-4-diethylamino-phenylazo)-4-chloro-benzenesulfonic acid 
• 108130-16-1 4-chloro-2-[(ethoxycarbonyl)amino]benzenesulfonyl chloride 
• 1083418-39-6 4-chloro-2-{[5-(4-chloro-phenyl)-2-trifluoromethyl-furan-3-carbonyl]-amino}-benzene-sulfonic acid 
• 1034331-54-8 2-((E)-3-biphenyl-4-yl-acryloylamino)-4-chloro-benzenesulfonic acid 
• 1034331-52-6 4-chloro-2-((E)-3-naphthalen-2-yl-acryloylamino)-benzenesulfonic acid 
• 89284-57-1 3-chloro-2,4,6-tribromoaniline 

Relevant academic research and scientific papers

1,2,4-Benzothiadiazine-1,1-dioxide derivatives as Ionotropic glutamate receptor ligands: Synthesis and structure-activity relationships

Ionotropic glutamate receptor (iGluR) modulators, specially AMPA receptor antagonists, are potential tools for numerous therapeutic applications in neurological disorders, including Alzheimer's and Parkinson's diseases, amyotrophic lateral sclerosis, epil

The efficient palladium-catalyzed selective t synthesis of benzenesulfonic acids

Palladium-catalyzed synthetic methodology has been developed for the synthesis of 2-aminobenzenesulfonic acids from benzothiazoles in good to excellent yields using chloramine-B in alkaline (pH 12) acetonitrile/water (1:1) at 80C.

Development of an efficient ruthenium catalyzed synthetic process and mechanism for the facile conversion of benzothiazoles to orthanilic acids

Ruthenium-Schiff base complex catalyzed efficient protocol has been developed for the synthesis of orthanilic acids from benzothiazoles in good to excellent yields using N-haloamines. Hexa-coordinated ruthenium complex with Schiff base and triphenylphosphine ligands has been prepared and its catalytic function was invented for the synthesis of orthanilic acids. The synthetic process utilizes our efficient method for the selective and preferential oxidation of thiazole ring of benzothiazoles using N-haloamines without effecting phenyl ring. The detailed catalytic, mechanistic and kinetic investigations have been made for the synthetic reactions. Solvent isotope studies have been made in H2O-D2O and the reactions were carried out at different temperatures. Under the identical set of conditions, the kinetics of catalyzed reactions has been compared with uncatalyzed reactions and found that the catalyzed reactions are 9-11 folds faster. The catalytic constants (KC) have been calculated for each N-haloamine at different temperatures and the values of activation parameters with respect to the catalyst have been evaluated. Spectroscopic evidence for the formation of 1:1 complex between N-haloamine and ruthenium has been obtained. The observed results have been explained by a plausible mechanism and the related rate law has been deduced.

Bioisosteric modifications of 2-arylureidobenzoic acids: Selective noncompetitive antagonists for the homomeric kainate receptor subtype GluR5

2-Arylureidobenzoic acids (AUBAs) have recently been presented as the first series of selective noncompetitive GluR5 antagonists. In this paper we have modified the acidic moiety of the AUBAs by introducing different acidic and neutral groups, and similarly, we have replaced the urea linker of the AUBAs with other structurally related linkers. Replacing the acid with neutral substituents led to inactive compounds in all instances, showing that an acidic moiety is necessary for activity. Replacing the carboxylic moiety in 2a with a sulfonic acid (5c) or a tetrazole ring (5d) improved the potency at GluR5 receptors (compounds 5c and 5d showed IC50 values of 1.5 and 2.0 μM, respectively, compared to compound 2a with IC50 = 4.8 μM). Compound 5c did not show improved in vivo activity in the ATPA rigidity test compared to 2a, whereas compound 5d was 4 times more potent than 2a. All compounds wherein the urea linker had been replaced showed lower or no activity. The results described extend the knowledge of structure-activity relationships for the AUBAs, and compound 5d may prove to be a good candidate for studying GluR5 receptors in vitro and in vivo.

NOVEL ARYL UREIDO BENZOIC ACID DERIVATIVES AND THEIR USE

This invention relates to novel aryl ureido benzoic acid derivatives useful as selective and non-competitive antagonists of the ionotropic GluR5 receptor. Due to their biological activity, the aryl ureido derivatives of the invention are considered useful for treating diseases that are responsive to modulation of an aspartate or a glutamate receptor. Moreover the invention provides chemical compounds for use according to the invention, as well as pharmaceutical compositions comprising the chemical compounds, and methods of treating diseases or disorders or conditions responsive to modulation of an aspartate or a glutamate receptor.

Process for the preparation of aminoarylsulphonic acids in sulfolene solvent

Aromatic aminosulphonic acids which have a reduced content of discoloring by-products are obtained when aromatic amines are reacted with a sulphonating agent in a reaction medium at least some of which consists of tetramethylene sulphone.

Barium laked phenylazonaphthalene dye containing sulfonic acid groups

Azo dyes containing sulfonic acid groups laked with barium and derived from an anilinesulfonic acid as diazo component and a β-naphtholsulfonic acid as coupling component for example a dye of the formula STR1 The dyes are eminently suitable as pigments for coloring surface coating compositions, printing inks and particlarly resins.