98-58-8 Usage
Description
4-Bromobenzenesulfonyl chloride is an organic compound that features a bromo group attached to a benzene ring, with a sulfonyl chloride group attached to the benzene ring as well. This chemical structure endows it with unique reactivity and properties that make it useful in various chemical and pharmaceutical applications.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 98-58-8 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, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 98-58:
(4*9)+(3*8)+(2*5)+(1*8)=78
78 % 10 = 8
So 98-58-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H4BrClO2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H
98-58-8Relevant articles and documents
Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts
Chen, Guang-Le,He, Shi-Hui,Cheng, Liang,Liu, Feng
supporting information, p. 8338 - 8342 (2021/10/25)
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.
Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst
Antonietti, Markus,Guldi, Dirk M.,Markushyna, Yevheniia,Savateev, Aleksandr,Schü?lbauer, Christoph M.,Ullrich, Tobias
supporting information, p. 20543 - 20550 (2021/08/12)
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.
Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
, (2021/09/20)
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.
