98-58-8

Usage

Uses

Used in Chemical Synthesis:
4-Bromobenzenesulfonyl chloride is used as an activating agent in the synthesis of oligodeoxyriboand oligoribo-nucleotides in solution. Its reactivity allows for the formation of stable phosphoramidite linkages, which are crucial for the construction of these nucleotide chains.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-Bromobenzenesulfonyl chloride is used for the identification of amines. This identification is essential for understanding the reactivity and potential applications of amine-containing compounds in drug development.
Used in the Synthesis of Specific Compounds:
4-Bromobenzenesulfonyl chloride is also utilized in the synthesis of 4-(N-allylsulfamoyl)phenylboronic acid, a compound that may have potential applications in the development of new pharmaceuticals or materials.
Used in Protection of Amines:
In chemical processes, amines can be sensitive to certain conditions. 4-Bromobenzenesulfonyl chloride is used to protect amines as 4-bromobenzenesulfonamides, which can be a crucial step in the synthesis of complex organic molecules where amine protection is necessary.
Used in Inhibition Studies:
4-Bromobenzenesulfonyl chloride is employed in the synthesis and inhibition studies of substituted N-L-histidinylphenylsulfonyl hydrazide. This application is significant for understanding the mechanisms of enzyme inhibition and the development of potential therapeutic agents.

Purification Methods

Wash the sulfonyl chloride with cold water, dry and recrystallise it from pet ether, or from ethyl ether cooled in powdered Dry-Ice after the ether solution had been washed with 10% NaOH until colourless, then dry it with anhydrous Na2SO4. Alternatively dissolve it in CHCl3, wash it with H2O, dry (Na2SO4), evaporate and recrystallise it. [Huntress & Carten J Am Chem Soc 62 511 1940.] Test for the SO2Cl group by dissolving it in EtOH and boiling with NH4CNS whereby a yellow amorphous precipitate forms on cooling. [Beilstein 11 IV 162.]

InChI:InChI=1/C6H4BrClO2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H

Upstream product

• 108-86-1 bromobenzene 
• 2028-85-5 (4-bromophenyl)diazonium chloride 
• 106-37-6 1.4-dibromobenzene 
• 126714-65-6 (4-bromophenyl)(methoxymethyl)sulfane 
• 106-40-1 4-bromo-aniline 
• 7790-94-5 chlorosulfonic acid 
• 7664-93-9 sulfuric acid 
• 589-87-7 1,4-bromoiodobenzene 
• 5153-67-3 nitrostyrene 
• 5335-84-2 bis(4-bromophenyl)disulfide 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 2297-64-5 p-bromophenylsulfonyl hydrazide 
• 127-65-1 chloroamine-T 
• 106-53-6 para-bromobenzenethiol 

Downstream Products

• 331972-47-5 4-bromo-N-(thiazol-2-yl)benzene sulfonamide 
• 131700-63-5 4-bromo-N-pyrimidin-2-ylbenzenesulfonamide 
• 885664-30-2 4-bromo-benzenesulfonic acid-(4-methyl-thiazol-2-ylamide) 
• 16293-92-8 4-bromo-benzenesulfonic acid-[1]naphthylamide 
• 6295-97-2 4-bromo-benzenesulfonic acid-(4-chloro-anilide) 
• 7454-72-0 4-bromo-N-(4-methoxyphenyl)benzenesulfonamide 
• 126145-99-1 4-((4-bromophenyl)sulfonamido)benzoic acid 
• 59724-43-5 4-bromo-N-(2-hydroxy-ethyl)-benzenesulfonamide 
• 2519-69-9 4-bromo-N-pentylbenzenesulfonamide 
• 500730-57-4 4-bromo-N-(2-hydroxy-2-methylpropyl)-benzenesulfonamide 
• 6419-78-9 4-bromo-N,N-dibutylbenzenesulfonamide 
• 331956-19-5 1-bromo-4-((4-methoxyphenyl)sulfonyl)benzene 
• 7463-25-4 4-bromo-benzenesulfonic acid o-tolyl ester 
• 3609-88-9 N-(2-phenylethyl)-4-bromobenzenesulfonamide 

Relevant academic research and scientific papers

NOVEL COMPOUND, PREPARATION METHOD THEREOF, AND USE THEREOF

The present invention relates to a method for preparing a biomaterial having selectively functionalized tyrosine, a biomaterial having selectively functionalized tyrosine, and a pharmaceutical composition containing the same as an active ingredient. The method for preparing a biomaterial to which a compound represented by formula 2 is coupled, of the present invention, allows the compound represented by formula 2 to be selectively coupled, in a high yield in a biomaterial, to tyrosine, which is present on the surface of an aqueous solution such that the coupling thereof to amino acids other than tyrosine does not occur and, when only one tyrosine is present, heterogeneous mixtures are not present and the inherent activity of the biomaterial is maintained, and thus the compound can be effectively used as a pharmaceutical composition containing a biomaterial drug as an active ingredient. In addition, the method can selectively functionalize tyrosine, and thus can be effectively used for tyrosine functionalization in a biomaterial.

Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts

We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.

Method for rapidly preparing N-benzenesulfonyl amino acid ester compound

The invention discloses a method for rapidly preparing an N-benzenesulfonyl amino acid ester compound. The invention mainly relates to chemical synthesis. A two-step one-pot strategy is adopted, substituted phenylmercaptan is used as a raw material, in-situ generated benzenesulfonyl chloride acts with hydrochloride of amino acid ester to obtain the N-benzenesulfonyl amino acid ester compound, the strategy is mild in condition, high in yield and high in reaction efficiency, and can be used for rapidly preparing the formula (I) compound and derivatives or analogues thereof. The method for rapidly preparing the N-benzenesulfonyl amino acid ester compound is simple to operate, mild in condition, high in yield and efficiency and relatively high in application value.

Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst

Among external stimuli used to promote a chemical reaction, photocatalysis possesses a unique one—light. Photons are traceless reagents that provide an exclusive opportunity to alter chemoselectivity of the photocatalytic reaction varying the color of incident light. This strategy may be implemented by using a sensitizer capable to activate a specific reaction pathway depending on the excitation light. Herein, we use potassium poly(heptazine imide) (K-PHI), a type of carbon nitride, to generate selectively three different products from S-arylthioacetates simply varying the excitation light and otherwise identical conditions. Namely, arylchlorides are produced under UV/purple, sulfonyl chlorides with blue/white, and diaryldisulfides at green to red light. A combination of the negatively charged polyanion, highly positive potential of the valence band, presence of intraband states, ability to sensitize singlet oxygen, and multi-electron transfer is shown to enable this chromoselective conversion of thioacetates.

High yielding protocol for direct conversion of thiols to sulfonyl chlorides and sulfonamides

In this paper, a new method for oxidative chlorination of thiols to sulfonyl chlorides and sulfonamides using H2O2 in the presence of TMSCl is reported. The excellent yields, short reaction times, excellent efficiencies, low costs, and easy separation of products are the most important advantages of this method.

Aromatic Chlorosulfonylation by Photoredox Catalysis

Visible-light photoredox catalysis enables the efficient synthesis of arenesulfonyl chlorides from anilines. The new protocol involves the convenient in situ preparation of arenediazonium salts (from anilines) and the reactive gases SO2and HCl (from aqueous SOCl2). The photocatalytic chlorosulfonylation operates at mild conditions (room temperature, acetonitrile/water) with low catalyst loading. Various functional groups are tolerated (e.g., halides, azides, nitro groups, CF3, SF5, esters, heteroarenes). Theoretical and experimental studies support a photoredox-catalysis mechanism.

A facile method for regioselective synthesis of new N-acetyl/thioacetyl-(E)-stilbene benzenesulfonamide derivatives via N-acetyl/thioacetyl sulfonamide formation

A series of new N-acetyl/thioacetyl-(E)-stilbene benzenesulfonamide derivatives were synthesized regioselectively in moderate to high yields by following a convenient, three-step procedure. The procedure consists of the direct oxidative conversion of a thiol compound to the corresponding sulfonyl chloride using TMSCl/KNO3, followed by a room temperature reaction in a one-pot transformation of the resultant sulfonyl chloride into N-acetyl/thioacetyl sulfonamide, which undergoes a further Pd-catalyzed coupling reaction, giving rise to the stilbene compounds reported for the first time.

NOVEL COMPOUNDS AS GPR119 AGONISTS

The present invention relates to novel compounds of formula (I) as GPR119 agonist, composition compositions containing such compounds and method of preparation thereof.

Aminoxidation of Arenethiols to N-Chloro-N-sulfonyl Sulfinamides

A simple and efficient method to synthesize N-chloro-N-sulfonylsulfinamides by the direct aminoxidation of arenethiols under aqueous and mild conditions is disclosed, geminally installing the oxo and amino groups on the sulfur atom of arenethiols. The products have been primarily developed as sulfinylation reagents to convert Grignard reagents into sulfoxides, and as amination reagents to convert secondary amines into hydrazine derivatives.