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
• Article Data: 9

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

Description

4-BIPHENYLSULFONIC ACID, also known as Biphenyl-4-sulfonic acid hydrate, is an organic compound with the chemical formula C12H9SO3H. It is a white crystalline solid that is soluble in water and has a high melting point. 4-BIPHENYLSULFONIC ACID is characterized by its aromatic structure, which consists of two phenyl rings connected by a sulfonic acid group. The presence of the sulfonic acid group imparts acidic properties to the molecule, making it a useful catalyst in various chemical reactions.

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

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

Downstream Products

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

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.

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.

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.