5790-69-2

Basic information

• Product Name: 2-Amino-5-chlorobenzenesulfonamide
• Synonyms: 2-Amino-5-chlorobenzenesulphonamide;2-Amino-5-chlorobenzenesulphonamide 96%;2-(Aminosulphonyl)-4-chloroaniline, 4-Chloro-2-sulphamoylaniline;2-Amino-5-chlorobenzenesulphonamide96%
• CAS NO: 5790-69-2
• Molecular Formula: C₆H₇ClN₂O₂S
• Molecular Weight: 206.65
• Mol File: 5790-69-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 148-150°C
• Boiling Point: 433.1 °C at 760 mmHg
• Flash Point: 215.7 °C
• Appearance: /
• Density: 1.558 g/cm³
• Vapor Pressure: 1.05E-07mmHg at 25°C
• Refractive Index: 1.637
• PKA: 10.02±0.60(Predicted)
• CAS DataBase Reference: 2-Amino-5-chlorobenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-chlorobenzenesulfonamide(5790-69-2)
• EPA Substance Registry System: 2-Amino-5-chlorobenzenesulfonamide(5790-69-2)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 5790-69-2(Hazardous Substances Data)

Usage

General Description

2-Amino-5-chlorobenzenesulfonamide, also known as sulfanilamide, is an organic compound with the chemical formula C6H6ClNO2S. It is a white to off-white powder that is soluble in water and ethanol. This chemical is commonly used as an antibacterial agent, particularly in the treatment of urinary tract infections. It works by inhibiting the growth of bacteria and is often combined with other antibiotics for a synergistic effect. Sulfanilamide has also been used in the production of dyes and as a component in some medications. However, its use has declined due to the development of more effective and less toxic antibiotics. It is important to handle this chemical with care as it is considered harmful if swallowed, inhaled, or absorbed through the skin, and can cause irritation to the eyes and skin.

InChI:InChI=1/C6H7ClN2O2S/c7-4-1-2-5(8)6(3-4)12(9,10)11/h1-3H,8H2,(H2,9,10,11)

Upstream product

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• 17800-60-1 2-acetylamino-benzenesulfonic acid acetylamide 
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Downstream Products

• 93899-88-8 7-chloro-3-phenethyl-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide 
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• 92294-64-9 7-chloro-3-cyclohex-2-enylmethyl-3,4-dihydro-2H-benzo[1,2,4]thiadiazine 1,1-dioxide 
• 51138-82-0 benzyl-(7-chloro-1,1-dioxo-1,2(4)-dihydro-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-amine 
• 94712-09-1 7-chloro-3-(3,4-diethoxy-phenyl)-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide 
• 3966-97-0 3-benzyl-7-chloro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide 
• 93187-23-6 7-chloro-3-cyclohexyl-2⁽⁴⁾H-benzo[1,2,4]thiadiazine 1,1-dioxide 
• 93309-25-2 7-chloro-3-phenoxymethyl-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide 
• 54734-82-6 2-amino-5-chloro-3-iodobenzenesulfonamide 
• 22503-72-6 IDRA 21 
• 92629-15-7 4-Chloro-2-sulfamoylcrotonoylanilide 
• 101064-10-2 N-(4-chloro-2-sulfamoyl-phenyl)-succinamic acid methyl ester 
• 364-98-7 diazoxide 
• 93867-16-4 3-Dimethylanilino-7-chlor-3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxid 

Relevant articles and documents

Method for preparing diazoxide

The invention discloses a method for preparing diazoxide. The method comprises the following steps: reacting o-aminobenzenesulfonamide with N-chlorosuccinimide in a chlorine solvent to obtain 2-amino-5-chlorobenzenesulfonamide, mixing the 2-amino-5-chlorobenzenesulfonamide, an imidazolium salt and an amide solvent, and heating the obtained mixture to react to obtain the diazoxide; or mixing o-aminobenzenesulfonamide, the imidazolium salt and the amide solvent, heating for a reaction to obtain a compound IV, and reacting the compound IV with N-chlorosuccinimide in the chlorine solvent so as toobtain the diazoxide. The invention also discloses an application of imidazole hydrochloride as a catalyst in the preparation of diazoxide. The method avoids the problems that chlorosulfonyl isocyanate and strong acid (sulfuric acid) which have high corrosivity and toxicity are used in the reaction process and the reaction temperature is high (240-250 DEG C), and the reaction steps are short; thetotal yield of the two steps can reach 90% or above; and compared with publicly reported diazoxide preparation methods, the synthesis method of the invention overcomes numerous defects, so that the synthesis method is suitable for industrial production.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF METABOLIC SYNDROME

The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of fo

Acetic acid derivatives of 3,4-dihydro-2 H-1,2,4-benzothiadiazine 1,1-dioxide as a novel class of potent aldose reductase inhibitors

A series of novel benzothiadiazine 1,1-dioxide derivatives were synthesized and tested for their inhibitory activity against aldose reductase. Of these derivatives, 17 compounds, having a substituted N2-benzyl group and a N4-acetic acid group on the benzothiadiazine, were found to be potent and selective aldose reductase inhibitors in vitro with IC50 values ranging from 0.032 to 0.975 μM. 9m proved to be the most active in vitro. The eight top-scoring compounds coming from the in vitro test for ALR2 inhibition activity were then tested in vivo, whereby three derivatives, 9i, 9j, and 9m, demonstrated a significantly preventive effect on sorbitol accumulation in the sciatic nerve in the 5-day streptozotocin-induced diabetic rats in vivo. Structure-activity relationship and molecular docking studies highlighted the importance of substitution features of N4-acetic acid group and halogen-substituted N2-benzyl group in the benzothiadiazine scaffold and indicated that substitution with hallogen at C-7 had a remarkably strong effect on ALR2 inhibition potency.