938-05-6

Basic information

• Product Name: N,N-DIBROMOBENZENESULFONAMIDE
• Synonyms: N,N-DIBROMOBENZENESULFONAMIDE;N,N-Dibromobenzenesulfonimide;Dibromamine B
• CAS NO: 938-05-6
• Molecular Formula: C₆H₅Br₂NO₂S
• Molecular Weight: 314.98
• Mol File: 938-05-6.mol

Chemical Properties

• Melting Point: 115 °C (decomp)
• Boiling Point: 351.5±25.0 °C(Predicted)
• Appearance: /
• Density: 2.123±0.06 g/cm3(Predicted)
• PKA: -27.85±0.70(Predicted)
• CAS DataBase Reference: N,N-DIBROMOBENZENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIBROMOBENZENESULFONAMIDE(938-05-6)
• EPA Substance Registry System: N,N-DIBROMOBENZENESULFONAMIDE(938-05-6)

Safety Data

• Hazardous Substances Data: 938-05-6(Hazardous Substances Data)

Upstream product

• 98-10-2 benzenesulfonamide 
• 16917-10-5 N-bromo-benzenesulfonamide; potassium-salt 
• 64-19-7 acetic acid 
• 127-52-6 chloramine-B 

Downstream Products

• 19871-46-6 1-Benzenesulfonyl-2-phenyl-aziridine 
• 98-10-2 benzenesulfonamide 
• 860516-03-6 N-(2-bromo-1-methyl-propyl)-benzenesulfonamide 
• 7467-11-0 2,5-dibromobenzenesulfonamide 
• 16917-10-5 N-bromo-benzenesulfonamide; potassium-salt 
• 22427-00-5 4-bromo-3-methoxy-1-butene 
• 62035-87-4 N-(1-methyl-pent-4-enyl)-benzenesulfonamide 
• 62035-86-3 N-(hex-5-en-1-yl)benzenesulfonamide 
• 62035-78-3 1,6-Bis-(benzolsulfonamido)-2,5-dibromhexan 
• 54378-60-8 N-(2-Bromo-2,2-dichloro-1-chloromethyl-ethyl)-benzenesulfonamide 
• 54378-59-5 C₉H₈Br₂Cl₃NO₂S 
• 92378-07-9 2-exo-Benzolsulfonsaeureamido-8-syn-brom-bicyclo<3,2,1>octan 

Relevant articles and documents

TRICYCLIC PYRIDONES AND PYRIMIDONES

A compound of Formula (I) is provided: (I) where the variables are defined herein.

ALKYLATED PIPERAZINE COMPOUNDS

Alkylated piperazine compounds of Formula I are provided, including stereoisomers, tautomers, and pharmaceutically acceptable salts thereof, useful for inhibiting Btk kinase, and for treating immune disorders such as inflammation mediated by Btk kinase. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, and treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

Catalysis and mechanistic studies of ruthenium and osmium on synthesis of anthranilic acids

Ruthenium, osmium and ruthenium + osmium catalyzed synthetic methodology was developed for the synthesis of anthranilic acids from indoles in good to excellent yields using bromamine-B in alkaline acetonitrile-water (1:1) at 313 K. Detailed catalysis studies of ruthenium, osmium and the mixture of both were carried out for the synthetic reactions. The positive synergistic catalytic activity of Ru(III) + Os(VIII) was observed to a large extent with the activity greater than the sum of their separate catalytic activities. Detailed kinetic and mechanistic investigations for each catalyzed reactions were carried out. The kinetic pattern and mechanistic picture of each catalyzed reaction were found to be different for each catalyst and to obey the underlying rate laws: rate = k[BAB]t[Indole][Ru(III)]x[OH-] y rate = k[BAB]t[Indole][Os(VIII)][OH-] y rate = k[BAB]t[Indole]o[Ru(III) + Os(VIII)][OH-]y where, x, y Os(VIII) > Ru(III). This trend may be attributed to the different d-electronic configuration of the catalysts. The proposed mechanisms and the rigorous kinetic models derived give results that fit well with the experimental data in each catalyzed reaction. Copyright

Palladium(II)-catalyzed oxidation of tranexamic acid by bromamine-B in alkaline medium and uncatalyzed reaction in acid medium: A study of kinetic and mechanistic chemistry

Tranexamic acid (TA) possess antifibrinolytic properties and finds extensive applications in pharmaceuticals. Its oxidation-kinetic study is of much significance in understanding the mechanistic profile of TA in biological systems. In this context, a systematic kinetic study of palladium(II) (Pd(II)) catalyzed oxidation of TA by sodium N-bromobenzenesulfonamide or bromamine-B (BAB) in alkaline medium and uncatalyzed reaction in perchloric acid medium at 303 K was investigated. In acid medium, the reaction exhibits a first-order dependence of rate on [BAB]o and less than unity order dependence on [TA]o. The reaction rate shows inverse less than unity order dependence with respect to [H+]. In alkaline medium, the reaction shows first-order dependence on both [BAB]o and [Pd(II)] and zero-order with respect to [TA]o. The order with respect to [OH -] is less than unity. Activation parameters have been evaluated. The oxidation reactions are nearly 10-fold faster in acid medium in comparison with alkaline medium. In alkaline medium, the Pd(II) catalyzed reactions are about 6-fold faster than the uncatalyzed reaction. Further, the catalytic constant (KC) has been calculated at different temperatures and activation parameters with respect to Pd(II) catalyst have also been evaluated. The conjugate acid C6H5SO2NHBr and the anion C 6H5SO2N-Br of BAB have been postulated as the reactive oxidizing species in acid and alkaline media, respectively. The proposed mechanisms and derived rate laws are in agreement with the observed kinetics.

Bromamine-B/PdCl2 is an efficient system for the synthesis of anthranilic acids from indoles and indigos

A convenient method has been developed for the conversion of indoles and indigos into anthranilic acids in good to excellent yields using a bromamine-B/PdCl2 system. The general process utilizes our efficient method for the oxidation of indoles and indigos in alkaline (pH 12) acetonitrile/water (1:1) at 60°C. Copyright Taylor & Francis Group, LLC.

Oxidation kinetics of some sulfoxides with N,N-dibromobenzene sulfonamide

The kinetics of oxidation of some sulfoxides with dibromamine-B yielding sulfones was investigated in presence of HgII, and the rate equation, kobs = k3K2K′h[S]/[RNH 2] + K′h was found to be valid. The reaction involves two distinct pathways namely initial fast step and a subsequent slow step. The chloride ions have no effect on the reactivity of sulfoxides. Sulfoxides containing electron-attracting substituents retard the reactivity while those containing electron-releasing constituents accelerate the rate of oxidation. Exner plot confirms the operation of same mechanism in all the sulfoxides studied. Electrophilic addition of Br+ to sulfur atom results in an electron-deficient sulfonium centre which decomposes in a slow rate-limiting step. The rate coefficients are treated in terms of multiparametric extensions of the Hammett equation to have more insight into the mechanistic aspects.

N,N-Dibromobenzenesulfonamide as a reagent for oxidative cleavage of oximes to their parent carbonyl compounds under non-aqueous and aprotic conditions

Deprotection of different oximes to their parent aldehydes and ketones in high yields has been carried out by using N,N-dibromobenzenesulfonamide(dibromoamine-b) under mild conditions.

N,N-Dibromobenzenesulfonamide: A useful regenrable reagent for bromination of various carbanionic substrates

N,N-Dibromobenzenesulfonamide(dibromoamine-B), which is prepared easily in high yield, has been employed as effective brominating agent for carbanionic substrates under mild conditions. β-Diketones and β-ketoesters were brominated by this reagent without using any bases. The reagent can be recovered, rebrominated, and reused several times.

Kinetic analysis of oxidation of dipeptides by sodium N-bromobenzenesulfonamide in acid medium: A mechanistic approach

The kinetics of the oxidation of five dipeptides (DPP) viz., glycylglycine (Gly-Gly), L-alanyl-L-alanine (Ala-Ala), L-valyl-L-valine (Val-Val), L-leucyl-L-leucine (Leu-Leu), and phenylglycyl-phenylglycine (Phg-Phg) by sodium N-bromobenzenesulfonamide or bromamine-B (BAB) in presence of HClO4 was studied at 40 °C. The five reactions followed identical kinetics with a first-order dependence on [BAB] and fractional order in [DPP]. At [H+] > 0.04 mol dm-3, the rate was inverse fractional in [H+], but zero order at lower [H+] (≤ 0.04 mol dm-3). A variation of the ionic strength or dielectric constant of the medium and the addition of halide ions and benzenesulfonamide had no effect on the rate of the reaction. Proton inventory studies were made in H2O-D2O mixtures for all five dipeptides. A Michaelis-Menten type mechanism has been suggested to explain the results. The decomposition and equilibrium constants were evaluated. The oxidation products were identified. The isokinetic temperature was 360 K, indicating the enthalpy to be a controlling factor. The rate of oxidation increased in the order Phg-Phg > Ala-Ala > Val-Val > Leu-Leu > Gly-Gly. The kinetics of oxidation of dipeptides was compared with those of their corresponding monomer amino acids, namely Phenylglycine, alanine, valine, leucine, and glycine. A general mechanism was proposed and the derived rate law are consistent with the observed kinetics.

Oxidation of ethanolamines by sodium N-bromobenzenesulfonamide in alkaline buffer medium: A kinetic and mechanistic study

The kinetics of oxidation of ethanolamines, monoethanolamine (MEA), diethanolamine (DEA), and triethanolamine (TEA), by sodium N-bromobenzenesulfonamide or bromamine-B (BAB) in alkaline buffer medium (pH 8.7-12.2) has been studied at 40°C. The three reactions follow identical kinetics with first-order in [oxidant] and fractional-order each in [substrate] and [OH-]. Under comparable experimental conditions, the rate of oxidation increases in the order: DEA > TEA > MEA. The added reaction product, benzenesulfonamide, retards the reaction rate. The addition of halide ions and the variation of ionic strength of the medium have no significant effect on the rate. The dielectric effect is negative. The solvent isotope effect k′(H2O)/k′(D2O) ≈ 0.92. Activation parameters for the composite reaction and for the rate-limiting step were computed from the Eyring plots, Michaelis-Menten type of kinetics is observed. The formation and decomposition constants of ethanolamine-BAB complexes are evaluated. An isokinetic relationship is observed with β = 430 K indicating that enthalpy factors control the rate. For each substrate, a mechanism consistent with the kinetic data has been proposed.