58236-74-1

Usage

Uses

Used in Organic Synthesis:
3-BROMOBENZYLSULFONYL CHLORIDE is used as a reagent for the synthesis of various organic compounds. Its sulfonyl chloride group and bromine atom on the benzyl ring facilitate multiple reaction pathways, making it a valuable intermediate in the preparation of complex molecules.
Used in Pharmaceutical Industry:
3-BROMOBENZYLSULFONYL CHLORIDE is used as a building block for the development of pharmaceutical compounds. Its reactivity allows for the creation of new drug candidates with potential therapeutic applications.
Used in Chemical Research:
3-BROMOBENZYLSULFONYL CHLORIDE is used as a research tool in academic and industrial laboratories. Its unique properties make it an interesting subject for studies on reaction mechanisms, synthetic strategies, and the development of new methodologies in organic chemistry.

InChI:InChI=1/C7H6BrClO2S/c8-7-3-1-2-6(4-7)5-12(9,10)11/h1-4H,5H2

Upstream product

• 932-77-4 3-bromobenzyl chloride 
• 823-78-9 meta-bromobenzyl bromide 

Downstream Products

• 446042-98-4 neopentyl 3-bromophenylmethanesulfonate 
• 446042-81-5 5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2,2-dimethylpentyl (3-bromophenyl)methanesulfonate 
• 803727-93-7 N,N-bis(2,4-dimethoxybenzyl)-1-(3-bromophenyl)methanesulfonamide 
• 803728-02-1 N,N-bis(2,4-dimethoxybenzyl)-1,1-difluoro-1-(3-bromophenyl)methanesulfonamide 
• 446043-00-1 neopentyl(3-bromophenyl)difluoromethanesulfonate 
• 446042-78-0 5-hydroxy-2,2-dimethylpentyl (3-bromophenyl)-difluoromethanesulfonate 
• 446043-02-3 neopentyl 3-(5-acetylthiophen-2-yl)methanesulfonate 
• 446042-83-7 5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2,2-dimethylpentyl (3-bromophenyl)-difluoromethanesulfonate 
• 919354-04-4 1-(3-bromophenyl)methanesulfonamide 
• 1160924-46-8 C₁₂H₁₇BrN₂O₂S 
• 1298109-32-6 C₁₈H₁₃BrF₅NO₄S 
• 1298109-21-3 C₁₃H₇BrF₅NO₂S 
• 1397712-36-5 [5-(3-bromophenyl)-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-[1,4,3]-oxathiazin-2-yl]cyclohexylamine 
• 1397712-40-1 cyclohexyl-[6,6-dimethyl-4,4-dioxo-5-(3-pyrimidin-5-yl-phenyl)-5,6-dihydro-4H-4lambda6-[1,4,3]-oxathiazin-2-yl]amine 

Relevant academic research and scientific papers

Alkyne Linchpin Strategy for Drug:Pharmacophore Conjugation: Experimental and Computational Realization of a Meta-Selective Inverse Sonogashira Coupling

The late-stage functionalization (LSF) of pharmaceutical and agrochemical compounds by the site-selective activation of C-H bonds provides access to diverse structural analogs and expands synthetically-accessible chemical space. We report a C-H functionalization LSF strategy that hinges on the use of an alkyne linchpin to assemble conjugates of sp2-rich marketed pharmaceuticals and agrochemicals with sp3-rich 3D fragments and natural products. This is accomplished through a template-assisted inverse Sonogashira reaction that displays high levels of selectivity for the meta position. This protocol is also amenable to distal structural modifications of α-amino acids. The transformation of alkyne functionality to other functional groups further highlights the applicative potential. Computational and experimental mechanistic studies shed light on the detailed mechanism. Turnover-limiting 1,2-migratory insertion of the bromoalkyne coupling partner occurs after relatively fast C-H activation. While this insertion occurs unselectively, regioconvergence results from one of the adducts undergoing a 1,2-trialkylsilyl migration to form the alkynylated product. A heterobimetallic Pd-Ag transition structure is essential for product formation in the β-bromide elimination step.

Rhodium-Catalyzed meta-C?H Functionalization of Arenes

Rhodium-catalyzed ortho-C?H functionalization is well known in the literature. Described herein is the Xphos-supported rhodium catalysis of meta-C?H olefination of benzylsulfonic acid and phenyl acetic acid frameworks with the assistance of a para-methoxy-substituted cyano phenol as the directing group. Complete mono-selectivity is observed for both scaffolds. A wide range of olefins and functional groups attached to arene are tolerated in this protocol.

Synthesis and receptor binding studies of novel 4,4-disubstituted arylalkyl/arylalkylsulfonyl piperazine and piperidine-based derivatives as a new class of σ1 ligands

This study presents the synthesis and biological evaluation of a new series of arylalkyl/arylalkylsulfonyl piperazine and piperidine-based derivatives as sigma receptor ligands. It was found that a number of halogen substituted sulfonamides display relatively high and low affinities to σ1 and σ2 receptors, respectively. The σ1 affinities and subtype selectivities of four piperidine derivatives were also found to be generally comparable to those of piperazine analogues. Compared to σ1-Rs compounds with n = 0 and 2, those with n = 1 proved to have optimal length of carbon chain by exhibiting higher affinities. Within this series, the 4-benzyl-1-(3-iodobenzylsulfonyl)piperidine sigma ligand was identified with 96-fold σ1/σ2 selectivity ratio (Kiσ1 = 0.96 ± 0.05 nM and K iσ2 = 91.8 ± 8.1 nM).

BENZOTHIAZOLE COMPOUNDS

The present invention relates to benzothiazole compounds that mimic the activity of BH3 only proteins and are capable of binding to and neutralizing pro survival Bcl 2 proteins. The invention also relates to the use of such compounds in the regulation of cell death or cell survival and the treatment and/or prophylaxis of diseases or conditions associated with the deregulation of cell death or cell survival.

Synthesis and PKCθ inhibitory activity of a series of 5-vinyl phenyl sulfonamide-3-pyridinecarbonitriles

A series of 5-vinyl phenyl sulfonamide-3-pyridinecarbonitriles were prepared and evaluated as PKCθ inhibitors. Optimization resulted in the identification of compound 15 with an IC50 value 0.44 nM for the inhibition of PKCθ with 150-fold select

TRICYCLIC INHIBITORS OF 5-LIPOXYGENASE

Described herein are compounds and pharmaceutical compositions containing such compounds, which inhibit the activity of 5-lipoxygenase (5-LO). Also described herein are methods of using such 5-LO inhibitors, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other leukotriene-dependent or leukotriene mediated conditions, diseases, or disorders.

Synthesis of α-fluorosulfonamides by electrophilic fluorination

(Chemical Equation Presented) α-Fluorosulfonamides were prepared by electrophilic fluorination of tertiary sulfonamides using N- fluorobenzenesulfonimide as fluorinating agent and utilizing the dimethoxybenzyl group (DMB) as a new sulfonamide protecting g

The difluoromethylenesulfonic acid group as a monoanionic phosphate surrogate for obtaining PTP1B inhibitors

Three peptides, 7-9, bearing sulfono(difluoromethyl)phenylalanine (F2Smp, 2), a nonhydrolyzable, monoanionic phosphotyrosine mimetic, were prepared and evaluated as PTP1B inhibitors. The most effective inhibitor was the nonapeptide, ELEF(F2Smp)MDYE-NH2, (9) which exhibited a Ki of 360 nM. A comparison of F2Smp-bearing peptides 7 [DADE(F2Smp)LNH2, Ki=3.4 μM] and 8 [EEDE(F2Smp)LNH2, Ki=0.74 μM] with their phosphono(difluoromethyl)phenylalanine (F2Pmp)-bearing analogues indicated that F2Smp is not as effective a pTyr mimetic as F2Pmp by 100- to 130-fold. Although F2Smp is not as effective as F2Pmp, a comparison of peptide 7 with analagous peptides bearing other monoanionic pTyr mimetics recently reported in the literature indicates that F2Smp is about 65-fold more effective than any other non-hydrolyzable, monanionic pTyr mimetic reported to date. To further assess the difluoromethylenesulfonic acid (DFMS) group as a monoanionic phosphate mimetic, a series of 24 nonpeptidyl biaryl compounds bearing the DFMS group were prepared using polymer-supported methodologies and screened for PTP1B inhibition. Several of these compounds were selected for further study and their IC50's compared to their difluoromethylenephosphonic (DFMP) analogues. The differences in IC50's between the DFMS and DFMP non-peptidyl compounds was not as great as with the F2Smp- and F2Pmp-bearing peptides. Possible reasons for this and its implication to the design of small molecule PTP1B inhibitors is discussed.