701-34-8

Basic information

• Product Name: 4-Bromobenzenesulfonamide
• Synonyms: 4-Bromobenzenesulfonamide, 97+%;4-BroMobenzenesulfonaMide >=99.0% (T);P-BROMOBENZENESULFONAMIDE;Benzenesulfonamide, 4-bromo-;Benzenesulfonamide, p-bromo-;p-bromo-benzenesulfonamid;AKOS 206-12;4-BROMOBENZENESULPHONAMIDE
• CAS NO: 701-34-8
• Molecular Formula: C₆H₆BrNO₂S
• Molecular Weight: 236.09
• EINECS: -0
• Product Categories: Aryl;Halogenated;Organohalides;blocks;Bromides;Sulfonamides
• Mol File: 701-34-8.mol

Chemical Properties

• Melting Point: 163-167 °C
• Boiling Point: 360.7°C (rough estimate)
• Flash Point: 171.9 °C
• Appearance: /
• Density: 1.8000 (estimate)
• Vapor Pressure: 7.57E-06mmHg at 25°C
• Refractive Index: 1.6140 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.89±0.10(Predicted)
• Water Solubility: 991.6mg/L(15 oC)
• BRN: 2691657
• CAS DataBase Reference: 4-Bromobenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromobenzenesulfonamide(701-34-8)
• EPA Substance Registry System: 4-Bromobenzenesulfonamide(701-34-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22
• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: DB0550000
• HazardClass: IRRITANT
• Hazardous Substances Data: 701-34-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromobenzenesulfonamide is used as a reagent for the preparation of cobalt(III) complexes of N,R-sulfonyldithiocarbimate anion. It plays a crucial role in the synthesis process, contributing to the development of new pharmaceutical compounds with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-Bromobenzenesulfonamide is utilized in the synthesis of 2-, 3-, and 4-(substituted-phenylethynyl)benzenesulfonamides. These synthesized compounds can be further used in the development of various chemical products, including pharmaceuticals, dyes, and other specialty chemicals.
Overall, 4-Bromobenzenesulfonamide is a valuable compound with applications in the pharmaceutical and chemical synthesis industries, contributing to the development of new compounds and products with potential benefits in various sectors.

InChI:InChI=1/C6H6BrNO2S/c7-5-2-1-3-6(4-5)11(8,9)10/h1-4H,(H2,8,9,10)

Upstream product

• 3466-32-8 4-bromoohenyl methyl sulfone 
• 7018-74-8 4-bromobenzenesulfonyl isocyanate 
• 6647-76-3 p-bromobenzenesulfonyl azide 
• 71106-34-8 1-<(tert-butyldimethylsilyl)oxy>-1,5-cyclohexanediene 
• 100981-43-9 ebrotidine 
• 877-99-6 1-methoxy-4-(2-methyl-1-propenyl)benzene 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 71-43-2 benzene 
• 7664-93-9 sulfuric acid 
• 500730-57-4 4-bromo-N-(2-hydroxy-2-methylpropyl)-benzenesulfonamide 
• 10035-10-6 hydrogen bromide 
• 211675-73-9 4-bromo-N-(3-phenyl-propyl)-benzenesulfonamide 
• 93281-65-3 4-bromo-(N-tert-butyl)benzenesulfonamide 
• 90944-62-0 N,N-diethyl-4-bromobenzenesulfonamide 

Downstream Products

• 98590-45-5 (4-bromo-benzenesulfonyl)-oxalamic acid methyl ester 
• 27715-57-7 N-(4-bromo-benzenesulfonyl)-phthalimide 
• 14067-99-3 N-((4-bromophenyl)sulfonyl)benzamide 
• 98273-63-3 (4-bromo-benzenesulfonyl)-formyl-amine 
• 1836-19-7 N,N-dichloro(p-BrC₆H₄)sulfonamide 
• 138-41-0 4-(aminosulfonyl)-benzoic acid 
• 74756-45-9 N,N-dibromo-4-bromobenzenesulfonamide 
• 98950-00-6 4-bromo-N-(2,3-dihydroxypropyl)benzenesulfonamide 
• 105208-51-3 4-bromo-benzenesulfonic acid-[bis-(2,3-dihydroxy-propyl)-amide] 
• 72856-18-9 (4-bromo-benzenesulfonyl)-carbamic acid ethyl ester 
• 152675-32-6 N-<(4-bromophenyl)sulfonyl>acetamide 
• 99990-43-9 4-bromo-benzenesulfonic acid-[bis-(2-cyano-ethyl)-amide] 
• 100874-17-7 3-(4-bromo-benzenesulfonylamino)-phthalide 
• 1156-18-9 di(4-bromobenzenesulfonyl)amine 

Relevant articles and documents

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

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.

Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups

We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.

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.

METHOD FOR PRODUCING OXIDE USING BETA-MANGANESE DIOXIDE

With the object of efficiently producing an oxidation product, the present invention provides a method for producing an oxidation product by oxidizing a raw material compound in the presence of oxygen, wherein the raw material compound is oxidized in the presence of manganese dioxide having a crystal structure of β-type.

NAPHTHYRIDINE DERIVATIVES AS PRC2 INHIBITORS

Disclosed are compounds of formula (I) or (II) that inhibit Polycomb Repressive Complex 2 (PRC2) activity. In particular, the present invention relates to compounds, pharmaceutical compositions and methods of use, such as methods of treating cancer using the compounds and pharmaceutical compositions of the present invention.

IMIDAZO[1,2-C]PYRIMIDINE DERIVATIVES AS PRC2 INHIBITORS FOR TREATING CANCER

Disclosed are compounds that inhibit Polycomb Repressive Complex 2 (PRC2) activity. In particular, disclosed are compounds of Formula (I) and pharmaceutical compositions thereof, and methods of using the compounds and pharmaceutical compositions in, for example, methods of treating cancer.

Palladium-Catalyzed ortho-Benzoylation of Sulfonamides through C?H Activation: Expedient Synthesis of Cyclic N-Sulfonyl Ketimines

The ortho-carbonylation of sulfonylarenes by non-hazardous aryl aldehydes as a carbonyl precursor was reported. In this method, the sulfonamide group serves as a directing group for C?H activation in the presence of a Pd catalyst under ligand-free conditions. The scope of this strategy has been extended to the one-pot two-step synthesis of cyclic N-sulfonyl ketimines under mild reaction conditions. Our approach could be considered as an alternative by circumventing the use of highly reactive organolithium or Grignard reagents to access a wide range of biologically potent cyclic N-sulfonyl ketimines. (Figure presented.).

New allyldithiocarbimate salts: Synthesis, structure and antifungal activity

Fifteen new allyldithiocarbimates were prepared from different allylic bromides and various potassium dithiocarbimates, yielding (Z)-2-(methoxycarbonyl)-3-(X-nitrophenyl)allyl-(N-R-sulfonyl)dithiocarbimates (where X = 2, 3 and 4; R = phenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl and 4-iodophenyl). These anions were isolated as tetraphenylphosphonium salts and characterized by HRMS, infrared, 1H and 13C NMR spectroscopies. Molecular electrostatic potentials were used to evaluate intermolecular interactions present in the new substances and to explain variations observed on their melting points. Single crystal X-ray diffraction experiments confirmed the Z stereochemistry of the allyldithiocarbimate anions. C–H?O, C–H?N, C–H?S and C–H?π intermolecular interactions in the solid state were studied by X-ray diffraction and Hirshfeld surface analyses. The new compounds inhibited the mycelial growth of various fungi species responsible for severe plant diseases. The allylithiocarbimates were especially active against Botrytis cinerea, with IC50 values as low as 20 μM, being more effective than the active principals of the commercial fungicides Ziram and Mancozeb.

Discovery of Sulfonamide-Derived Agonists of SOS1-Mediated Nucleotide Exchange on RAS Using Fragment-Based Methods

The nucleotide exchange factor Son of Sevenless (SOS) catalyzes the activation of RAS by converting it from its inactive GDP-bound state to its active GTP-bound state. Recently, we have reported the discovery of small-molecule allosteric activators of SOS1 that can increase the amount of RAS-GTP in cells. The compounds can inhibit ERK phosphorylation at higher concentrations by engaging a feedback mechanism. To further study this process, we sought different chemical matter from an NMR-based fragment screen using selective methyl labeling. To aid this process, several Ile methyl groups located in different binding sites of the protein were assigned and used to categorize the NMR hits into different classes. Hit to lead optimization using an iterative structure-based design paradigm resulted in compounds with improvements in binding affinity. These improved molecules of a different chemical class increase SOS1cat-mediated nucleotide exchange on RAS and display cellular action consistent with our prior results.

PRC2 INHIBITORS

The present invention relates to compounds that inhibit Polycomb Repressive Complex 2 (PRC2) activity. In particular, the present invention relates to compounds, pharmaceutical compositions and methods of use, such as methods of treating cancer using the compounds and pharmaceutical compositions of the present invention. (Formula (I))