3899-90-9

Basic information

• Product Name: P-TOLUENESULFONIC ACID 3-NITROPHENYL ESTER
• Synonyms: 3-nitrophenyltosylate;4-methyl-benzenesulfonicaci3-nitrophenylester;m-nitrophenyltosylate;p-toluenesulfonicacid,m-nitrophenylester;3-NITROPHENYL P-TOLUENESULFONATE;P-TOLUENESULFONIC ACID 3-NITROPHENYL ESTER;Toluenesulfonicacidnitrophenylester;m-Nitrophenyl p-toluenesulfonate
• CAS NO: 3899-90-9
• Molecular Formula: C₁₃H₁₁NO₅S
• Molecular Weight: 293.3
• Mol File: 3899-90-9.mol

Chemical Properties

• Melting Point: 113 °C
• Boiling Point: 453°Cat760mmHg
• Flash Point: 227.8°C
• Appearance: /
• Density: 1.388g/cm³
• Vapor Pressure: 5.74E-08mmHg at 25°C
• Refractive Index: 1.604
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: P-TOLUENESULFONIC ACID 3-NITROPHENYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: P-TOLUENESULFONIC ACID 3-NITROPHENYL ESTER(3899-90-9)
• EPA Substance Registry System: P-TOLUENESULFONIC ACID 3-NITROPHENYL ESTER(3899-90-9)

Safety Data

• RTECS: XT7130000
• Hazardous Substances Data: 3899-90-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
P-Toluenesulfonic acid 3-nitrophenyl ester is used as a reagent for its high reactivity and electrophilicity, facilitating the acylation and alkylation of nucleophiles in organic chemistry.
Used in Pharmaceutical Synthesis:
It is used as a coupling agent in the synthesis of pharmaceuticals, contributing to the formation of complex organic compounds necessary for drug development.
Used in Dye Production:
P-Toluenesulfonic acid 3-nitrophenyl ester is utilized in the production of dyes, where its reactivity aids in the synthesis of various colorants for different applications.
Used in Catalyst Applications:
In various chemical reactions, P-Toluenesulfonic acid 3-nitrophenyl ester is used as a catalyst to promote the formation of carbon-carbon and carbon-heteroatom bonds, enhancing the efficiency of these processes.
Used in Fine Chemicals Production:
Its wide utility in the production of fine chemicals is attributed to its ability to catalyze crucial bond formations, making it an essential component in the synthesis of specialty chemicals.

InChI:InChI=1/C13H11NO5S/c1-10-5-7-13(8-6-10)20(17,18)19-12-4-2-3-11(9-12)14(15)16/h2-9H,1H3

Upstream product

• 554-84-7 meta-nitrophenol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 31540-75-7 1-((dichloromethyl)sulfonyl)-4-methylbenzene 
• 2460-58-4 2-hydroxy-4-nitrobenzaldehyde 
• 16855-08-6 2-hydroxy-6-nitrobenzaldehyde 
• 90151-04-5 4-hydroxy-2-nitrobenzaldehyde 
• 134654-00-5 m-(2-imidazolylazo)phenyl p-toluenesulfonate 
• 134654-01-6 m-(2-imidazolylazo)phenol 
• 554-84-7 meta-nitrophenol 
• 104-15-4 toluene-4-sulfonic acid 
• 189759-53-3 3-nitro-4-(toluene-4-sulfonylmethyl)phenyl toluene-4-sulfonate 
• 93184-10-2 2^I-O-(p-toluenesulfonyl)-α-cyclodextrin 
• 84216-71-7 2^I-O-(p-toluenesulfonyl)-β-cyclodextrin 
• 3865-15-4 3-aminophenyl tosylate 

Relevant articles and documents

Gold(I)-Catalyzed N-Desulfonylative Amination versus N-to-O 1,5-Sulfonyl Migration: A Versatile Approach to 1-Azabicycloalkanes

Valuable 1-azabicycloalkane derivatives have been synthesized through a novel gold(I)-catalyzed desulfonylative cyclization strategy. An ammoniumation reaction of ynones substituted at the 1-position with an N-sulfonyl azacycle took place in the presence of a gold cation by intramolecular cyclization of the disubstituted sulfonamide moiety onto the triple bond. Depending on the size of the heterocyclic ring and substitution of the substrates, two unprecedented forms of nucleophilic attack on the sulfonyl group were exploited, that is, a N-desulfonylation in the presence of an external protic O nucleophile (37–87 %, 10 examples) and a unique N-to-O 1,5-sulfonyl migration (60–98 %, 9 examples).

Graphite/methanesulfonic acid (GMA) as a new reagent for sulfonylation of phenols and thia-Fries rearrangement of aryl sulfonates to sulfonylphenols

A new facile method for direct sulfonylation of phenols was developed. Graphite in methanesulfonic acid (GMA) was used to prepare sulfonylphenols by sulfonylation of phenol and naphthalene derivatives with p-toluenesulfonic acid (=4-methylbenzenesulfonic acid) (Table 1) and the thia-Fries rearrangement of aryl sulfonates (Table 4). Mechanistic studies showed that the sulfonylation reaction of phenols in GMA occurred through an initial sulfonate formation followed by a thia-Fries rearrangement of the aryl sulfonate by an intermolecular mechanism (Scheme 3).