100-03-8

Basic information

• Product Name: p-chlorobenzenesulphinic acid
• Synonyms: p-chlorobenzenesulphinic acid;4-Chlorobenzenesulfinicacid;P-CHLORO BENZENE SULFINIC ACID
• CAS NO: 100-03-8
• Molecular Formula: C₆H₅ClO₂S
• Molecular Weight: 176.6207
• EINECS: 202-812-2
• Mol File: 100-03-8.mol

Chemical Properties

• Melting Point: 99 °C
• Boiling Point: 251°C (estimate)
• Flash Point: 173.9 °C
• Appearance: solid
• Density: 1.3872 (estimate)
• Vapor Pressure: 6.22E-06mmHg at 25°C
• Refractive Index: 1.694
• PKA: 1.14±0.10(Predicted)
• CAS DataBase Reference: p-chlorobenzenesulphinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: p-chlorobenzenesulphinic acid(100-03-8)
• EPA Substance Registry System: p-chlorobenzenesulphinic acid(100-03-8)

Safety Data

• Hazardous Substances Data: 100-03-8(Hazardous Substances Data)

Usage

Chemical Properties

solid

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 36, p. 2652, 1988 DOI: 10.1248/cpb.36.2652

InChI:InChI=1/C6H5ClO2S/c7-5-1-3-6(4-2-5)10(8)9/h1-4H,(H,8,9)

Upstream product

• 64-17-5 ethanol 
• 4875-10-9 o-nitrothiophenol 
• 112071-03-1 4-chloro-benzenethiosulfonic acid S-(2-nitro-phenyl ester) 
• 17333-85-6 4-chlorophenyldiazonium salt 
• 349-89-3 p-chlorobenzenesulfonyl fluoride 
• 5445-04-5 2-amino-3-(4-chloro-benzenesulfonyl)-propionic acid 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 108-90-7 chlorobenzene 
• 141-52-6 sodium ethanolate 
• 123-54-6 acetylacetone 
• 106-47-8 4-chloro-aniline 
• 536-57-2 p-toluene sulfinic acid 
• 6028-82-6 3-methyl-2-phenylpyrrocoline 
• 1142-97-8 phenyl 4-chlorobenzenethiosulfonate 

Downstream Products

• 5943-04-4 chloromethyl p-chlorophenyl sulfone 
• 90396-00-2 p-chlorophenylsulfonylpropionic acid 
• 101894-78-4 benzhydryl-(4-chloro-phenyl)-sulfone 
• 32748-30-4 1-chloro-4-((dichloromethyl)sulfonyl)benzene 
• 61624-30-4 (E)-1,2-bis(4-chlorophenylsulphonyl)ethylene 
• 102078-58-0 (4-chloro-phenyl)-(4-methyl-benzhydryl)-sulfone 
• 101936-08-7 (4-chloro-benzhydryl)-(4-chloro-phenyl)-sulfone 
• 15953-53-4 (4-chloro-benzenesulfonyl)-methanol 
• 2901-92-0 p-chlorophenylsulfinyl chloride 
• 19770-81-1 2-(4-chloro-benzenesulfonyl)-N⁴,N⁴-dimethyl-p-phenylenediamine 
• 6269-31-4 2-((4-chlorophenyl)sulfonyl)benzene-1,4-diol 
• 52962-88-6 N-(4-chloro-benzenesulfonyl)-N,N'-bis-(morpholine-4-carbonyl)-hydrazine 
• 41998-12-3 (p-Chlorphenylsulfonylmethyl)-methylaether 
• 64533-17-1 1-Chloro-4-(1-methoxy-ethanesulfonyl)-benzene 

Relevant articles and documents

Synthesis of Substituted Pyrroles via Copper-Catalyzed Cyclization of Ethyl Allenoates with Activated Isocyanides

A new method for the synthesis of di- and trisubstituted pyrroles via copper-catalyzed cyclization of ethyl allenoates with activated isocyanides has been developed. In contrast to related annulation reactions previously reported, this new process features a skeletal rearrangement in which the aryl sulfonyl moiety, which functions as the electron-withdrawing group in the α-carbon of the isocyanide, was found to migrate to the γ-carbon of the starting allenoate in the final product for the first time.

Reduction of Sulfonic Acids and Related Organosulfur Compounds with Triphenylphosphine-Iodine System

Arenesulfonic acids, their sodium salts, and alkyl arenesulfonates can be reduced readily to the corresponding arenethiols quantitatively by treatment with a mixture of triphenylphosphine and a catalytic amount of iodine, while alkanesulfonic acids, sulfinic acids, disulfides, thiosulfonic S-esters, and sulfonates are also readily reduced to the corresponding thiols similarly.Upon treatment with a mixture of triphenylphosphine and excess iodine, however, these aliphatic sulfur compounds are converted eventually to the corresponding alkyl iodides.The relative reactivities of these sulfonyl derivatives in the reaction with the triphenylphosphine-iodine system are the following.Aromatic series: ArSO2Cl, ArSO2SAr' > ArSO2H > ArSO3R > ArSO3-HNBu3+ (or PyH+) > ArSO3H > ArSO2SO2Ar >> ArSO2CH2C(CH3)3, ArSO3Ar'.Aliphatic series: RSO2Cl, RSO2SR', RSO2-HNBu3+ > RSO3-HNBu3+ > RSSR, RSO2H > RSO3H > RSH > RSO3R'.In these reactions, the arenesulfonic acids bearing electron-donating substituents can be reduced more readily than those having electron-withdrawing substituents.

Photoredox Catalyzed Sulfonylation of Multisubstituted Allenes with Ru(bpy)3Cl2 or Rhodamine B

A highly regio- and stereoselective sulfonylation of allenes was developed that provided direct access to α, β-substituted unsaturated sulfone. By means of visible-light photoredox catalysis, the free radicals produced by p-toluenesulfonic acid reacted with multisubstituted allenes to obtain Markovnikov-type vinyl sulfones with Ru(bpy)3Cl2 or Rhodamine B as photocatalyst. The yield of this reaction could reach up to 91%. A series of unsaturated sulfones would be used for further transformation to some valuable compounds.

tert-Butyl Hydroperoxide-Initiated Radical Cyclization of 1-(Allyloxy)-2-(1-Arylvinyl)Benzenes with Sulfinic Acids to Access Sulfonated Benzoxepines

A tert-butyl hydroperoxide-initiated radical cyclization of 1-(allyloxy)-2-(1-arylvinyl)benzenes with sulfinic acids for the construction of sulfonated benzoxepines is developed. This reaction involves a radical pathway and offers a straightforward route to the formation of seven-membered ring via sulfonylation/cyclization process. This methodology features mild reaction conditions, a broad substrate scope and good functional group tolerance. (Figure presented.).

Visible-Light-Induced Radical Cascade Cyclizations of 1,7-Enynes with Sulfinic Acids: Direct Access to Sulfonated Chromanes and Sulfonated Tetrahydroquinolines under Metal-Free Conditions

Visible-light-induced strategy to access sulfonated chromanes and sulfonated 1,2,3,4-tetrahydroquinolines via a radical cascade cyclization of 1-(arylethynyl)-2-(vinyloxy)benzenes and N-allyl-2-(arylethynyl)anilines with aromatic and aliphatic sulfinic acids has been developed. In the presence of TBHP (7.5 mol%) as an oxidant and Eosin Y (3.0 mol%) as a photocatalyst, the reactions undergo smoothly to afford the corresponding products in good yields at room temperature under metal-free conditions. This transformation features low loading of TBHP, mild reaction conditions, simple operation, broad functional-group tolerance, and good yields of products. (Figure presented.).

Synergistic combination of visible-light photo-catalytic electron and energy transfer facilitating multicomponent synthesis of β-functionalized α,α-diarylethylamines

A synthetic strategy with the visible-light photo-catalytic synergistic combination of electron and energy transfer processes has been developed. The mild reaction conditions allow the radical-radical cross-coupling phenomenon for the multicomponent synthesis of β-arylsulfonyl(diarylphosphinoyl)-α,α-diarylethyl-amines from readily available arylsulfinic acids (diarylphosphine oxides), 1,1-diarylethylenes and arylazides.

Direct Substitution of Secondary and Tertiary Alcohols to Generate Sulfones under Catalyst- and Additive-Free Conditions

An environmentally benign protocol that affords propargylic sulfones containing highly congested carbon centers from easily accessible alcohols and sulfinic acids with water as the only byproduct is reported. The reaction proceeded via an in situ dehydrative cross-coupling process by taking advantage of the synergetic actions of multiple hydrogen bonds rather than relying on an external catalyst and/or additives to achieve high product distribution.

Tert-Butyl Nitrite Promoted Oxidative Intermolecular Sulfonamination of Alkynes to Synthesize Substituted Sulfonyl Pyrroles from the Alkynylamines and Sulfinic Acids

tert-Butyl nitrite promoted oxidative intermolecular sulfonamination of alkynes to synthesize substituted sulfonyl pyrroles from the alkynylamines and sulfinic acids via tandem addition/cyclization was developed. This reaction is performed well by employing tert-butyl nitrite as the oxidant, and various substituted sulfonyl pyrroles are formed in moderate to good yields with no requirement of metal catalysis.

Method for synthesizing aryl sulfonic acid by utilizing sulfur dioxide

The invention relates to a method for synthesizing aryl sulfonic acid by utilizing sulfur dioxide. The method is characterized by comprising the following steps that S1, aromatic hydrocarbon is added into a solvent, stirring is performed to achieve complete dissolution, and then a catalyst is added; S2, under the stirring condition and the conditions of 0-100 DEG C and 0-10 atm, dried excessive sulfur dioxide gas or sulfur dioxide liquid are added, and reaction is performed for 0.5-50 hours; S3, the reaction liquid obtained in the step S2 is cooled to 10 DEG C or below, pressurized filtration is performed, and a catalyst is recovered; S4, filtrate is distilled to recover unreacted sulfur dioxide, then the solvent is recovered through distillation, the residual solid is the product aryl sulfonic acid, and the product yield is higher than 85%. The raw materials for the method for synthesizing the aryl sulfonic acid by utilizing the sulfur dioxide are cheap and easy to obtain, the product yield is high, the production process is safer, ad the severe environmental pollution of a traditional process is greatly reduced.

Visible-Light Photocatalytic Bicyclization of 1,7-Enynes toward Functionalized Sulfone-Containing Benzo[a]fluoren-5-ones

A new visible-light photocatalytic arylsulfonylation and bicyclization of C(sp3)-tethered 1,7-enynes with sulfinic acids has been developed, delivering functionalized sulfone-containing benzo[a]fluoren-5-ones with generally good yields. This Eosin Y-catalyzed approach makes use of visible light as a safe and eco-friendly energy source to drive cascade cyclization reactions, resulting in continuous multiple bond-forming events including C–S and C–C bonds to efficiently construct polycyclic-linked alkyl aryl sulfones. (Figure presented.).