81903-80-2

Basic information

• Product Name: 3,4-DIBROMOBENZENESULFONYL CHLORIDE
• Synonyms: 3,4-DIBROMOBENZENESULFONYL CHLORIDE
• CAS NO: 81903-80-2
• Molecular Formula: C₆H₃Br₂ClO₂S
• Molecular Weight: 334.41
• Mol File: 81903-80-2.mol

Chemical Properties

• Melting Point: 34 °C
• Boiling Point: 346.9 °C at 760 mmHg
• Flash Point: 163.6 °C
• Appearance: /
• Density: 2.11 g/cm³
• Vapor Pressure: 0.000112mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: 3,4-DIBROMOBENZENESULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIBROMOBENZENESULFONYL CHLORIDE(81903-80-2)
• EPA Substance Registry System: 3,4-DIBROMOBENZENESULFONYL CHLORIDE(81903-80-2)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39
• RIDADR: 3261
• HazardClass: MOISTURE SENSITIVE, CORROSIVE
• Hazardous Substances Data: 81903-80-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3,4-DIBROMOBENZENESULFONYL CHLORIDE is used as a reagent for introducing the sulfonamide functional group into various organic molecules, facilitating the synthesis of a wide range of compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 3,4-DIBROMOBENZENESULFONYL CHLORIDE is utilized as a key intermediate in the synthesis of sulfonamide-based drugs, contributing to the development of new therapeutic agents.
Used in Dye and Pigment Production:
3,4-DIBROMOBENZENESULFONYL CHLORIDE is employed in the production of dyes and pigments, playing a crucial role in the creation of colorants for various applications.
Used in Fine Chemicals Production:
3,4-DIBROMOBENZENESULFONYL CHLORIDE is also used in the manufacturing of various fine chemicals, highlighting its broad applicability across different chemical industries.
Safety Considerations:
Due to its corrosive and toxic properties, 3,4-DIBROMOBENZENESULFONYL CHLORIDE is classified as a hazardous material, necessitating careful handling and proper safety measures during its use and storage.

InChI:InChI=1/C6H3Br2ClO2S/c7-5-2-1-4(3-6(5)8)12(9,10)11/h1-3H

Upstream product

• 583-53-9 2,3-dibromobenzene 
• 7790-94-5 chlorosulfonic acid 
• 7664-93-9 sulfuric acid 

Downstream Products

• 81902-96-7 3,4-Dibromo-N-methyl-benzenesulfonamide 
• 81902-97-8 3,4-Dibromo-N-ethyl-benzenesulfonamide 
• 224824-30-0 1-((3,4-dibromophenyl)sulfonyl)-1H-imidazole 
• 224824-31-1 1-(3,4-dibromophenylsulfonyl)indole 
• 224824-27-5 1-(3,4-dibromophenylsulfonyl)pyrrole 
• 904734-39-0 [18F]2-fluoroethyl 3,4-dibromobenzenesulfonate 
• 345892-69-5 3,4-Dibromo-N-[4-chloro-3-(2-dimethylamino-ethoxy)-phenyl]-benzenesulfonamide 

Relevant articles and documents

A convenient one-pot synthesis of boroxoles from diboronic acid

The preparation of the boroxole motif traditionally relies on a 3-step process and the use of n-butyl lithium that can limit substrate scope. Herein during our exploration toward novel RORγ inhibitors, we identified a convenient one-pot preparation of the motif in good yields with good substrate scope.

Palladium-Catalysed Desulfitative Heck Reaction Tolerant to Aryl Carbon-Halogen Bonds for Access to (Poly)halo-Substituted Stilbene or Cinnamate Derivatives

The palladium-catalysed desulfitative Heck type reaction of (poly)halo-substituted benzenesulfonyl chlorides with alkenes was investigated. Styrene or acrylates in the presence of bromo- or iodobenzenesulfonyl chlorides and a phosphine-free palladium catalyst were found to afford the expected β-arylated Heck type products with complete regio- and stereoselectivities. The reaction tolerates a variety of substituents on the halobenzenesulfonyl chloride. Moreover, no cleavage of the C-Br and C-I bonds was observed in the course of these reactions, allowing further transformations. Using 4-bromobenzenesulfonyl chloride as the central unit, consecutive desulfitative Heck type reaction followed by palladium-catalysed direct arylation allowed to prepare heteroarylated stilbene derivatives in only two steps.

Synthesis and radiopharmacological characterisation of a fluorine-18-labelled azadipeptide nitrile as a potential PET tracer for invivo imaging of cysteine cathepsins

A fluorinated cathepsin inhibitor based on the azadipeptide nitrile chemotype was prepared and selected for positron emission tomography (PET) tracer development owing to its high affinity for the oncologically relevant cathepsins L, S, K and B. Labelling with fluorine-18 was accomplished in an efficient and reliable two-step, one-pot radiosynthesis by using 2-[18F]fluoroethylnosylate as a prosthetic agent. The pharmacokinetic properties of the resulting radiotracer compound were studied invitro, exvivo and invivo in normal rats by radiometabolite analysis and small-animal positron emission tomography. These investigations revealed rapid conjugate formation of the tracer with glutathione in the blood, which is associated with slow blood clearance. The potential of the developed 18F-labelled probe to image tumour-associated cathepsin activity was investigated by dynamic small-animal PET imaging in nude mice bearing tumours derived from the human NCI-H292 lung carcinoma cell line. Computational analysis of the obtained image data indicated the time-dependent accumulation of the radiotracer in the tumours. The expression of the target enzymes in the tumours was confirmed by immunohistochemistry with specific antibodies. This indicates that azadipeptide nitriles have the potential to target thiol-dependent cathepsins invivo despite their disadvantageous pharmacokinetics.

Heterocyclic aromatic amide protecting groups for aryl and phthalocyaninesulfonic acids

Pyrroles, indole, imidazole, and a pyrazole were treated with 3,4-dibromobenzenesulfonyl chloride to form 3,4-dibromobenzenesulfonamides. The 1-(3,4-dibromophenylsulfonyl)pyrrole and 1-(3,4-dibromophenylsulfonyl)indole were stable to CuCN in DMF to produce 1-(3,4-dicyanophenylsulfonyl)pyrrole and 1-(3,4-dicyanophenylsulfonyl)indole, which upon treatment with ammonia in 2-N,N-dimethylaminoethanol gave the protected phthalocyanine-2,9,16,23-tetrasulfonamides. Base cleavage of these sulfonamides yielded the free acids. A mixed condensation of 4,5-diheptylphthalonitrile and 1-(3,4-dicyanophenylsulfonyl)pyrrole gave 9,10,16,17,23,24-hexakis(1-heptyl)-2-(1-pyrrolylsulfonyl)phthalocyanine. Cleavage of the latter yielded the lithium salt of the monosulfonic acid.