26971-85-7

Basic information

• Product Name: 1-chloro-4-(4-nitrophenoxy)sulfonyl-benzene
• Synonyms: 1-chloro-4-(4-nitrophenoxy)sulfonyl-benzene
• CAS NO: 26971-85-7
• Molecular Formula: C₁₂H₈ClNO₅S
• Molecular Weight: 313.71
• Mol File: 26971-85-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 484.8°Cat760mmHg
• Flash Point: 247°C
• Appearance: /
• Density: 1.516g/cm³
• Vapor Pressure: 4.4E-09mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: 1-chloro-4-(4-nitrophenoxy)sulfonyl-benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-chloro-4-(4-nitrophenoxy)sulfonyl-benzene(26971-85-7)
• EPA Substance Registry System: 1-chloro-4-(4-nitrophenoxy)sulfonyl-benzene(26971-85-7)

Safety Data

• Hazardous Substances Data: 26971-85-7(Hazardous Substances Data)

Usage

Usage

Building block in the synthesis of pharmaceuticals and agrochemicals

Physical State

White to off-white solid

Solubility

Insoluble in water, soluble in organic solvents

Reactivity

Versatile reagent with a wide range of applications

Precursor

Synthesis of biologically active compounds

Chemical Structure

Sulfonamide compound with a chlorine atom and a nitrophenyl group attached to a benzene ring

Utility

Useful for various chemical reactions and transformations in organic synthesis

InChI:InChI=1/C12H8ClNO5S/c13-9-1-7-12(8-2-9)20(17,18)19-11-5-3-10(4-6-11)14(15)16/h1-8H

Upstream product

• 100-02-7 4-nitro-phenol 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 14752-66-0 sodium p-chlorobenzenesulphinate 

Downstream Products

• 22771-98-8 N,N-Pentamethylen-4-chlorbenzol-sulfonamid 
• 100-02-7 4-nitro-phenol 
• 98-66-8 4-chloro-benzenesulfonic acid 
• 10504-94-6 4-chloro-N-(4-methylbenzyl)benzenesulfonamide 
• 14309-92-3 N-benzyl-4-nitroaniline 
• 10504-90-2 N-benzyl-4-chlorobenzenesulfonamide 
• 349397-05-3 4-chloro-N-(4-methoxybenzyl)benzenesulfonamide 

Relevant articles and documents

Electrochemical cross-coupling reactions of sodium arenesulfinates with thiophenols and phenols

A green electrochemical oxidative cross-coupling protocol for the generation of thiosulfonates and sulfonate esters using sodium arenesulfinates and thiophenols/phenols is disclosed. The protocol involves using inorganic and non-toxic NaI as both redox catalyst and supporting electrolyte at room temperature without oxidant and base. The reactions provide good yields of products and tolerate broad substrate scope. The mechanistic studies revealed that the reactions proceed via a radical pathway for the formation of SO2–S and SO2–O bonds.

Competitive Reaction Pathways in the Nucleophilic Substitution Reactions of Aryl Benzenesulfonates with Benzylamines in Acetonitrile

The reactions of aryl benzenesulfonates (YC6H4SO2OC6H4Z) with benzylamines (XC6H4CH2NH2) in acetonitrile at 65.0 deg C have been studied. The reactons proceed competitevely by S-O (kS-O) and C-O (kC-O) bond scission, but the former provides the major reaction pathway. On the basis of analysis of the Hammet and Broensted coefficients together with the cross-interaction constants ρXY, ρYZ, and ρXZ, stepwise mechanisms are proposed in which the S-O bond cleavage proceeds by rate-limiting formation of a trigonal-bipyramidal pentacoordinate (TBP-5C) intermediate, whereas the C-O bond scission takes place by rate-limiting expulsion of the sulfonate anion (YC6H4SO3-) from a Meisenheimer-type complex.