3406-84-6

Basic information

• Product Name: 4,4'-BIPHENYLDISULFONYL CHLORIDE
• Synonyms: [1,1'-Biphenyl]-4,4'-disulfonyl dichloride;4,4'-Biphenylylenedisulfonyl chloride;p,p'-Diphenyldisulfonyl chloride;BIPHENYL-4,4'-DISULFONYL CHLORIDE;4,4'-BIPHENYLDISULFONYL CHLORIDE;4,4'-BIPHENYLDISULFONYL DICHLORIDE;4,4'-DIPHENYLDISULFONYL CHLORIDE;4,4'-bis(phenylsulphonyl) dichloride
• CAS NO: 3406-84-6
• Molecular Formula: C₁₂H₈Cl₂O₄S₂
• Molecular Weight: 351.23
• EINECS: 222-293-6
• Product Categories: Biphenyls (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds
• Mol File: 3406-84-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 205-208 °C(lit.)
• Boiling Point: 476.7 °C at 760 mmHg
• Flash Point: 242.1 °C
• Appearance: /
• Density: 1.54 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Decomposes in contact with water,Insoluble in water
• BRN: 2222668
• CAS DataBase Reference: 4,4'-BIPHENYLDISULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-BIPHENYLDISULFONYL CHLORIDE(3406-84-6)
• EPA Substance Registry System: 4,4'-BIPHENYLDISULFONYL CHLORIDE(3406-84-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 3406-84-6(Hazardous Substances Data)

Usage

Description

4,4'-BIPHENYLDISULFONYL CHLORIDE, also known as Biphenyl-4,4′-disulfonyl chloride, is an organic compound that is characterized by its ability to react with various substrates, particularly in the synthesis of complex molecules. It possesses a unique chemical structure that allows it to form stable bonds with other molecules, making it a versatile reagent in chemical reactions.

Uses

Used in Chemical Synthesis:
4,4'-BIPHENYLDISULFONYL CHLORIDE is used as a reagent for the synthesis of complex organic molecules. It is particularly useful in the formation of stable bonds with other molecules, making it a valuable component in the creation of various compounds.
Used in the Synthesis of Cyclofructan:
In the field of carbohydrate chemistry, 4,4'-BIPHENYLDISULFONYL CHLORIDE is used as a reagent for the synthesis of 6A,6D-diamino-6A,6D-dideoxy-β-cyclodextrin. It reacts with cycloinulohexaose in pyridine to form capped cyclofructan, 6A,6C-di-O-(biphenyl-4,4′-disulfonyl)-cycloinulohexaose, which is an important intermediate in the synthesis of cyclodextrin derivatives.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 4,4'-BIPHENYLDISULFONYL CHLORIDE may also find applications in the pharmaceutical industry, where it could be used in the development of new drugs or drug delivery systems. Its ability to form stable bonds with other molecules makes it a potential candidate for the synthesis of various pharmaceutical compounds.

Upstream product

• 92-52-4 biphenyl 
• 51137-59-8 biphenyl-4,4'-disulfenyl chloride 
• 6954-27-4 (1,1'-biphenyl)-4,4'-dithiol 
• 108-95-2 phenol 
• 5314-37-4 4,4'-biphenyldisulfonic acid 
• 337984-45-9 4,4'-bis(benzylthio)biphenyl 

Downstream Products

• 7218-46-4 N,N'-bis-benzenesulfonyl-biphenyl-4,4'-disulfonamide 
• 6954-27-4 (1,1'-biphenyl)-4,4'-dithiol 
• 108651-62-3 biphenyl-4,4'-disulfonic acid bis-(2,5-diethoxy-4-amino-anilide) 
• 53999-54-5 4,4'-(biphenyl-4,4'-disulfonyl)-bis-morpholine 
• 130798-67-3 3,3'-<4,4'-biphenyldiylbis(sulfonylamino)>bis(1,5-naphthalenedisulfonic acid) tetrasodium salt 
• 130798-65-1 4,4'-<4,4'-biphenyldiylbis(sulfonylamino)>bis(5-hydroxy-2,7-naphthalenedisulfonic acid) tetrasodium salt 
• 42933-52-8 biphenyl-4,4'-disulfonic acid dihydrazide 
• 31139-42-1 4,4'-biphenyldisulfonic acid disodium salt 
• 53999-46-5 N,N'-diphenyl-biphenyl-4,4'-disulfonamide 
• 2995-93-9 4,4'-Bis-(3-trifluormethyl-phenylmercapto)-biphenyl 
• 1433-00-7 4,4'-bis-benzenesulfonyl-biphenyl 
• 3548-13-8 4,4'-Bis-(biphenyl-4-sulfonyl)-biphenyl 

Relevant articles and documents

Synthesis of novel biphenyl bis-sulfonamide based surfactants of expected biological activity

THIS STUDY explores the effect of structural changes of novel sulfonamide based-surfactants on surfactant behavior and antimicrobial activity. In order to better meet this as our primary goal, three different series, biphenyl-4,4′-disulfonamides (Series A, A1-4), amine acid salts of bis (2-aminophenyl) biphenyl-4,4′-disulfonamide (Series B, B 1-4) and their corresponding copper and cobalt complexes (Series C, C1-2) were prepared. The structures of the desired compounds were confirmed by using elemental analysis, Fourier transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (1H NMR) and UV-Vis spectral analysis. In addition to these spectroscopic measurements, compounds C1 and C2 (Series C) were subsequently characterized extensively by atomic absorption methods. Also as our secondary goal, we have measured surface properties as follows: surface tension (γ), critical micelle concentration (cmc), the surface excess concentration (Γmax) and the cross-sectional area per adsorbed surfactant head group (Amin). The investigation was continued to cover the antibacterial and antifungal screening for all synthesized compounds. In addition, some selected compounds were screened for cytotoxicity against human tumor cell lines - MCF7 (breast carcinoma), HEPG2 (liver carcinoma) and HCT116 (colon carcinoma).

CYCLISATION OF DIARYL COMPOUNDS WITH CHLOROSULFONIC ACID

Biphenyl (1) and other compounds of type PhXPh (X = O (19); S (30); NH (33); CH2 (40); (CH2)2 (41); (CH2)3 (51); C(CH3)2 (55)) were reacted with chlorosulfonic acid.Under forcing conditions (100-150 deg C), compounds 1, 19, 33, 40, 41, and 55 afforded the cyclic sulfones (2, 26, 27, 39, 43, 46, and 63).Cyclisation occurred most readily with diphenylethane (41) to give the 7-membered sulfone 46).On the other hand, diphenylsulfide (30) and diphenylpropane (51) failed to give cyclic products, while 2,2-diphenylpropane (55) afforded only a low yield of the cyclic compound (63) among a mixture of uncyclised products (57, 61, 62).With chlorosulfonic acid under milder conditions, the substrates afforded mono-, di-, tri- and tetra-sulfonyl chlorides which have been converted into 32 sulfonamides for screening as candidate medicinals and pesticides.The spectroscopic properties of selected compounds are briefly discussed with special reference to the orientation of sulfonation.Key words: Biphenyl; diphenyl compounds (PhXPh, X = O, S, NH, (CH2)n, C(CH3)2); chlorosulfonation.

Synthesis of aromatic sulfonyl chlorides - monomers for sulfur-containing polycondensation polymers

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