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98-10-2

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98-10-2 Usage

Description

Benzenesulfonamide is an organic compound that consists of a benzene ring attached to a sulfonamide group. It is a white to off-white granular crystalline powder with specific chemical properties, such as being insoluble in water but soluble in ethanol and ether, as well as in alkali.

Uses

Used in Biospecific Adsorption:
Benzenesulfonamide is used as a component in self-assembled monolayers of alkanethiolates on gold, which facilitates the biospecific adsorption of carbonic anhydrase. This application aids in the development of a model system for studying lateral steric effects.
Used in Pharmaceutical Modifications:
Benzenesulfonamide is utilized in the modification of pharmaceutical compounds, such as ciprofloxacin, where its presence at the c-7 position alters the primary target in Streptococcus pneumoniae from topoisomerase IV to gyrase.
Used in the Development of COX-2 Inhibitors:
Polar substitutions in the benzenesulfonamide ring of celecoxib have been found to produce a potent 1,5-diarylpyrazole class of COX-2 inhibitors, which are important in the development of anti-inflammatory drugs.
Used in Environmental Analysis:
Benzenesulfonamide is employed in the development of analytical methods for the simultaneous determination of benzotriazole, benzothiazole, and benzenesulfonamide contaminants in environmental waters, contributing to the monitoring and control of water pollution.

Preparation

Benzenesulfonamide is obtained by amination of benzenesulfonyl chloride.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 7201, 1994 DOI: 10.1016/0040-4039(94)85360-6Synthesis, p. 1031, 1986 DOI: 10.1055/s-1986-31862

Biological Activity

benzenesulfonamide, the amide of benzenesulfonic acid, has been used to produce various derivatives, especially those used as intermediates in the synthesis of photochemicals, dyes, disinfectants, as well as pharmaceuticals.

Biochem/physiol Actions

Benzenesulfonamide is an inhibitor of human carbonic anhydrase B. Benzenesulfonamide derivatives are effective in the treatment of proliferative diseases such as cancer. It is used in the synthesis of dyes, photochemicals and disinfectants.

Safety Profile

Moderately toxic by ingestion andintraperitoneal routes. When heated to decomposition itemits very toxic fumes of SOx and NOx.

in vitro

in a previous study, a series of n-aryl-β-alanine- and diazo-derivatives of benzenesulfonamide were designed, synthesized, and their binding affinities to carbonic anhydrases (ca) i, ii, vi, vii, xii, and xiii was investigated by the use of isothermal titration calorimetry and fluorescent thermal shift assay. the results indicated that 4-substituted diazobenzenesulfonamides were found to be most potent ca binders among the synthesized derivatives. in addition, the majority of the n-aryl-β-alanine derivatives had better affinity for ca ii while diazobenzenesulfonamides showed nanomolar affinities towards ca i isozyme. moreover, the x-ray crystallographic data showed the binding modes of both derivative groups [1].

in vivo

in the rat cpe model, the most potnet benzenesulfonamide indole derivative at 10 mg/kg in the mc/tw formulation displayed oral efficacy. moreover, this compound, when administered in another preferred, minimal formulation in the same in vivo model, demonstrated superior oral efficacy to the lead phenylmethane sulfonamide way-196025 orally administered in a lipid-based formulation. in addition, this benzenesulfonamide indole derivative was also orally efficacious at 1 mg/kg by attenuating both lar and the associated ahr to aerosolized carbachol in naturally sensitized sheep, which had been challenged through the airways with a. suum antigen [2].

references

[1] rutkauskas k et al. 4-amino-substituted benzenesulfonamides as inhibitors of human carbonic anhydrases. molecules. 2014 oct 28;19(11):17356-80. [2] lee kl et al. benzenesulfonamide indole inhibitors of cytosolic phospholipase a2α: optimization of in vitro potency and rat pharmacokinetics for oral efficacy. bioorganic and medicinal chemistry. 2008 16(3), 1345-1358.

Check Digit Verification of cas no

The CAS Registry Mumber 98-10-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 8 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 98-10:
(4*9)+(3*8)+(2*1)+(1*0)=62
62 % 10 = 2
So 98-10-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H7NO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H2,7,8,9)

98-10-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A10891)  Benzenesulfonamide, 98+%   

  • 98-10-2

  • 250g

  • 380.0CNY

  • Detail
  • Alfa Aesar

  • (A10891)  Benzenesulfonamide, 98+%   

  • 98-10-2

  • 1000g

  • 1211.0CNY

  • Detail
  • Alfa Aesar

  • (A10891)  Benzenesulfonamide, 98+%   

  • 98-10-2

  • 5000g

  • 4831.0CNY

  • Detail
  • Aldrich

  • (108146)  Benzenesulfonamide  ≥98%

  • 98-10-2

  • 108146-5G

  • 271.44CNY

  • Detail
  • Aldrich

  • (108146)  Benzenesulfonamide  ≥98%

  • 98-10-2

  • 108146-100G

  • 396.63CNY

  • Detail
  • Aldrich

  • (108146)  Benzenesulfonamide  ≥98%

  • 98-10-2

  • 108146-500G

  • 1,014.39CNY

  • Detail
  • Vetec

  • (V900785)  Benzenesulfonamide  Vetec reagent grade, 98%

  • 98-10-2

  • V900785-100G

  • 115.83CNY

  • Detail
  • Vetec

  • (V900785)  Benzenesulfonamide  Vetec reagent grade, 98%

  • 98-10-2

  • V900785-500G

  • 359.19CNY

  • Detail

98-10-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Benzenesulfonamide

1.2 Other means of identification

Product number -
Other names mandb7973

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:98-10-2 SDS

98-10-2Relevant articles and documents

MECHANISTIC INVESTIGATIONS WITH POSITIVE HALOGENS: KINETICS OF OXIDATION OF THIOSEMICARBAZIDE BY CHLORAMINE-B, BROMAMINE-B AND DICHLORAMINE-B IN ACID MEDIUM

Gowda, B. Thimme,Bhat, J. Ishwara

, p. 2119 - 2128 (1987)

Kinetics of oxidation of thiosemicarbazide (TSC) by chloramine-B (CAB), and bromamine-B (BAB) in aqueous perchloric acid medium and by dichloramine-B (DCB) in 1:1 (v/v) water-methanol medium has been studied.The rate followed first order kinetics in and inverse fractional order in with all the oxidants.But it was fractional order in with CAB and independent of with BAB and DCB.Addition of benzenesulphonamide, the reduced product of the oxidants had no effect on the rate with CAB and BAB but it slightly increased the rate with DCB.Therate decreased with increase in ionis strength of the medium in all cases.Decrease of dielectric constant of the reaction medium by adding methanol had no effect on the rate with CAB and BAB but increased the rate with DCB.The mechanisms proposed and the derived rate laws are in conformity eith the observed results.The coefficients of the rate limiting steps have been calculated.Kinetics observed with HOCl and HOBr support the proposed mechanisms.

Synthesis and X-Ray Structure of Bistetraphenylphosphonium Tris(phenylsulphonylimino)sulphite

Roesky, Herbert W.,Schmieder, W.,Sheldrick, William S.

, p. 1013 - 1014 (1981)

An aza-analogue of sulphite, the structure of which was determined by X-ray diffraction, is prepared from sodium amide and a sulphur di-imide in liquid ammonia.

Chloraminometric and bromaminometric oxidation of sulfanilic acid in alkaline medium: A comparative kinetic and mechanistic study

Puttaswamy,Jagadeesh

, p. 48 - 56 (2006)

The kinetics of oxidation of sulfanilic acid (SAA) by chloramine-B (CAB) and bromamine-B (BAB) has been investigated in alkaline medium at 35 ± 0.1°C. The oxidation reaction follows identical kinetics in the case of both the oxidants with first-order dependence on each [oxidant]o and [SAA]o and an inverse first-order dependence on [OH-]. The variation of ionic strength, dielectric constant of the medium, addition of the reaction product (benzene-sulfonamide), and halide ions showed no significant influence on the reaction rate. Proton inventory studies made in H2O-D2O mixtures for CAB and BAB have been utilized to calculate the isotopic fractionation factor. The reaction has been studied at different temperatures, and activation parameters for the composite reaction have been computed from the Arrhenius plots. N-Hydroxylaminobenzene-4-sulfonic acid was identified as the oxidation product of SAA from IR and GC-MS analysis. A mechanism consistent with the kinetic results is proposed in which PhSO 2NHX (X = Cl or Br) interact with the substrate in the rate-limiting step. A suitable rate law is derived. The rate of oxidation of sulfanilic acid is about fourfold faster in BAB compared to CAB. The oxidation of SAA brought about by CAT and BAT was also investigated under identical experimental conditions, and the overall rate of oxidation of SAA increases in the order: BAB > BAT > CAB > CAT This may be attributed to the difference in electrophilicities of Cl+ and Br+ ions and also the van der Waal's radii of chlorine and bromine.

SELECTIVE NON-CYCLIC NUCLEOTIDE ACTIVATORS FOR THE CAMP SENSOR EPAC1

-

Paragraph 00174-00176; 00198; 00277, (2021/09/26)

The invention relates generally to novel EPAC1 activators, such as Formula (I) and (II) and the preparation thereof as well as the use of EPAC1 activators disclosed herein as to selectively activate EPAC1 in cells.

Synthesis of magnetic chitosan supported metformin-Cu(II) complex as a recyclable catalyst for N-arylation of primary sulfonamides

Ahmadpoor, Fatemeh,Nasrollahzadeh, Mahmoud,Nezafat, Zahra,Pakzad, Khatereh

, (2021/06/25)

The application of chitosan, which has received much attention as a natural polymer and effective support, has many advantages such as biodegradability and biocompatibility. In this study, the immobilization of a copper complex on the magnetic chitosan bearing metformin ligand has been developed through immobilizing structurally defined metformin with long tail of (3-chloropropyl)trimethoxysilane (TMOS). The synthesized Fe3O4-chitosan@metformin-Cu(II) complex (Fe3O4-CS@Met-Cu(II)) was used as an effective, reusable and magnetic catalyst in the N-arylation of different derivatives of primary sulfonamides with arylboronic acids in ethanol. The primary sulfonamides were prepared from the reaction of sulfonyl chlorides with sodium cyanate in water under ultrasonic irradiation. Utilizing a wide variety of substrates in EtOH as a green solvent, high yields of the primary and secondary sulfonamides, easy work-up along with the excellent recovery and reusability of the catalyst, make this process a simple, economic and environmentally benign method. The synthesized Fe3O4-CS@Met-Cu(II) was characterized using various techniques such as XRD (X-ray diffraction), EDS (energy-dispersive X-ray spectroscopy), elemental mapping, TEM (transmission electron microscopy), FESEM (field emission scanning electron microscopy), VSM (vibrating sample magnetometer), ICP-MS (inductively coupled plasma mass spectroscopy), TGA (thermogravimetric analysis) and FT-IR (Fourier-transform infrared spectroscopy) analyses. The catalyst can be recycled and reused 5 times with no considerable loss of catalytic activity.

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