2113-68-0

Basic information

• Product Name: 4-BIPHENYLSULFONIC ACID
• Synonyms: P-DIPHENYLSULFONIC ACID;[1,1’-biphenyl]-4-sulfonicacid;4-Biphenylsulfonic;4-hydroxybiphenyl-O-sulfonic acid;4-BIPHENYLSULPHONIC ACID MONOHYDRATE 98%;3-(TRIFLUOROMETHYL)PHENYLTHIOURE;Biphenyl-4-sulfonic acid;Biphenyl-4-sulfonic acid hydrate, tech. 85%
• CAS NO: 2113-68-0
• Molecular Formula: C₁₂H₁₀O₃S
• Molecular Weight: 234.27
• EINECS: 218-717-4
• Mol File: 2113-68-0.mol

Chemical Properties

• Melting Point: 135-138°C
• Appearance: Odorless white powder
• Density: 1.319 g/cm³
• PKA: -0.61±0.50(Predicted)
• Water Solubility: Soluble in water.
• BRN: 2107412
• CAS DataBase Reference: 4-BIPHENYLSULFONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BIPHENYLSULFONIC ACID(2113-68-0)
• EPA Substance Registry System: 4-BIPHENYLSULFONIC ACID(2113-68-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• TSCA: Yes
• HazardClass: 8
• Hazardous Substances Data: 2113-68-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
4-BIPHENYLSULFONIC ACID is used as a catalyst for the hydrolysis of cellulose to prepare D-glucose with higher yield. It serves as a more effective catalyst than sulfuric acid for cellulose hydrolysis, making it a preferred choice in the production of D-glucose from cellulosic materials.
The use of 4-BIPHENYLSULFONIC ACID in the chemical industry is primarily due to its ability to act as a catalyst in the hydrolysis of cellulose. Cellulose is a complex carbohydrate found in the cell walls of plants, and its hydrolysis is an essential process in the production of glucose, a vital component in various industries, including food, pharmaceuticals, and biofuels. The use of 4-BIPHENYLSULFONIC ACID as a catalyst in this process allows for a higher yield of D-glucose, making it a more efficient and cost-effective method compared to using sulfuric acid.
In addition to its application in the chemical industry, 4-BIPHENYLSULFONIC ACID may also find use in other industries, such as pharmaceuticals, where its acidic properties could be utilized in the synthesis of various drugs and pharmaceutical compounds. Furthermore, its ability to act as a catalyst in chemical reactions could be applied in the development of new materials and processes in the field of materials science.

InChI:InChI=1/C12H10O3S/c13-16(14,15)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,(H,13,14,15)/p-1

Upstream product

• 1591-31-7 4-iodo-biphenyl 
• 98-80-6 phenylboronic acid 
• 92-52-4 biphenyl 
• 19813-90-2 4-biphenylthiol 

Downstream Products

• 1598422-94-6 (S,E)-methyl 3-(4-(2-([1,1′-biphenyl]-4-ylsulfonamido)-3-(1H-indol-3-yl)propoxy)phenyl)acrylate 
• 686350-93-6 4-{(1R)-2-[(6-{4-[3-(cyclopentylsulfonyl)phenyl]butoxy}-hexyl)amino]-1-hydroxyethyl}-2-(hydroxymethyl)phenol 4-biphenylsulfonate salt 
• 2051-62-9 4'-biphenyl chloride 
• 92-69-3 4-Phenylphenol 
• 1623-93-4 4-diphenylsulfonyl chloride 

Relevant articles and documents

Facile synthesis of diarylsulfones from arenes and 3CdSO4·xH2O via mechanochemistry

A variety of substituted diarylsulfones could be synthesized by simple arenes and 3CdSO4·xH2O in the presence of P2O5 under high-speed ball milling. It was suggest the aromatic sulfonation was performed by arene and in situ generated H2SO4, following-up by electrophilic substitution with another arene to give diarylsulfone.

Sustainable access to sulfonic acids from halides and thiourea dioxide with air

A sustainable and mild one-step strategy is explored for the synthesis of aryl and alkyl sulfonic acids using a facile combination of halides and sulfur dioxide surrogates under air. The cheap industrial material thiourea dioxide was employed as an eco-friendly and easy-handling sulfur dioxide surrogate, while air was used as a green oxidant. Both aryl and alkyl sulfonic acids were obtained under transition metal-catalyzed or transition metal-free conditions. Mechanistic studies demonstrated that sulfinate was involved as an intermediate in this transformation. Notably, this protocol has been applied to the late-stage sulfonation of the drugs naproxen, isoxepac and ibuprofen.

Fragment-Based Design, Synthesis, and Biological Evaluation of 1-Substituted-indole-2-carboxylic Acids as Selective Mcl-1 Inhibitors

Based on a known selective Mcl-1 inhibitor, 6-chloro-3-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-1H-indole-2-carboxylic acid, we applied a fragment-based approach to obtain new molecules that extended into the p1 pocket of the BH3 groove and then exhibited binding selectivity for the Mcl-1 over the Bcl-2 protein. After we deconstructed the 1H-indole-2-carboxylic acid from the parental molecule, a benzenesulfonyl was substituted at the 1-position to adopt a geometry preferred for accessing the p1 pocket according to the binding mode of the parental molecule identified by X-ray crystallography. A linear relationship between the free energy of ligand binding (ΔG) and the count of non-hydrogen heavy atoms (HAC) was maintained during the molecular growing to occupy the p1 pocket. Finally, we not only obtained compound 12 with a 7.5-fold selectivity to Mcl-1 (Ki = 0.48 μM by fluorescence polarization) over Bcl-2 (Ki = 3.6 μM), but also provided evidence that additional occupation of the p1 pocket is more favorable for Mcl-1 than for Bcl-2 binding, and contributes more to Mcl-1 inhibition than occupation of the p2 pocket. Compound 12 exhibited a selective killing ability on Mcl-1-dependent cancer cells.

Structure-activity relationships and pharmacokinetic analysis for a series of potent, systemically available biphenylsulfonamide matrix metalloproteinase inhibitors

A series of biphenylsulfonamide derivatives of (S)-2-(biphenyl-4- sulfonylamino)-3-methylbutyric acid (5) were prepared and evaluated for their ability to inhibit matrix metalloproteinases (MMPs). For this series of compounds, our objective was to systematically replace substituents appended to the biphenyl and α-position of 5 with structurally diverse functionalities to assess the effects these changes have on biological and pharmacokinetic activity. The ensuing structure-activity relationship (SAR) studies showed that biphenylsulfonamides substituted with bromine in the 4'- position (11c) significantly improved in vitro activity and exhibited superior pharmacokinetics (C(max), t(1/2), AUCs), relative to compound 5. Varying the lipophilicity of the α-position by replacing the isopropyl group of 11c with a variety of substituents, in general, maintained potency versus MMP-2, -3, and -13 but decreased the oral systemic availability. Subsequent evaluation of its enantiomer, 11c', showed that both compounds were equally effective MMP inhibitors. In contrast, the corresponding hydroxamic acid enantiomeric pair, 16a (S-isomer) and 16a' (R-isomer), stereoselectivity inhibited MMPs. For the first time in this series, 16a' provided nanomolar potency against MMP-1, -7, and -9 (IC50'S = 110, 140, and 18 nM, respectively), whereas 16a was less potent against these MMPs (IC(50)'S = 24, 78, and 84 μM, respectively). However, unlike 11c, compound 16a' afforded very low plasma concentrations following a single 5 mg/kg oral dose in rat. Subsequent X-ray crystal structures of the catalytic domain of stromelysin (MMP-3CD) complexed with inhibitors from closely related series established the differences in the binding mode of carboxylic acid-based inhibitors (11c,c') relative to the corresponding hydroxamic acids (16a,a').

Exploiting differences in solution vs solid-supported reactivity for the synthesis of sulfonic acid derivatives

(matrix presented) Quantitative We describe a method herein for the protection of aryl and alkyl sulfonates during synthesis which employs commercially available Wang or MBOH resin, both of which terminate as benzyl alcohols, as both a protecting group and "traceless" linker. Given the known instability of benzylic sulfonate esters to nucleophilic displacement in solution, this linkage is surprisingly stable: no loss of either aryl or alkyl sulfonates is observed when the resin is exposed to a wide variety of organic bases and solvents at room temperature. Further elaboration of the resin-bound sulfonates via Suzuki coupling is also described.

Two New Protecting Groups for the Guanidino Function of Arginine

Two new synthons, Fmoc-L-Arg(biphenyl-4-sulphonyl)-OH (8) and Fmoc-Arg(4-methoxy-3-t-butylbenzenesulphonyl)-OH (14), are prepared for the synthesis of arginine-containing peptides.These groups are cleaved by commonly employed trifluoroacetic acid and methanesulphonic acid.Kinetic studies reveal that extended bicyclic aromatic conjugation, as in biphenyl, slightly improves the acid lability compared to the electron-donating t-butyl group.

ORIENTATION IN THE SULFONATION OF BIPHENYL IN SULFURIC ACID SYSTEMS

Previously obtained calculated data on the orientation during the monosulfonation of biphenyl with 100percent sulfuric acid in the presence of O.2 mole/kg of nitrobenzene were confirmed by a flow technique.With dilution of the system to 7.5 mole/kg with nitrobenzene the ortho/para and meta/para ratios decrease by 500 and 40 times respectively.The probable reasons for this phenomenon are discussed.