640-60-8

Basic information

• Product Name: P-TOLUENESULFONIC ACID PHENYL ESTER
• Synonyms: AURORA KA-983;PHENYL P-TOLUENESULFONATE;PHENYLTOSYLATE;P-TOLUENESULFONIC ACID PHENYL ESTER;Toluenesulfonicacidphenylester;(Tosyloxy)benzene;4-Methylbenzenesulfonic acid phenyl ester;Phenyl tosylate,98%
• CAS NO: 640-60-8
• Molecular Formula: C₁₃H₁₂O₃S
• Molecular Weight: 248.3
• Mol File: 640-60-8.mol
• Article Data: 80

Chemical Properties

• Melting Point: 94-98 °C
• Boiling Point: 155-158 °C(Press: 7 Torr)
• Appearance: White to beige/Crystalline Powder
• Density: 1.245±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: P-TOLUENESULFONIC ACID PHENYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: P-TOLUENESULFONIC ACID PHENYL ESTER(640-60-8)
• EPA Substance Registry System: P-TOLUENESULFONIC ACID PHENYL ESTER(640-60-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• Hazardous Substances Data: 640-60-8(Hazardous Substances Data)

Usage

Chemical Properties

white to beige crystalline powder

Uses

Phenyl Tosylate is an intermediate in synthesizing Diclofenac-13C6 Sodium Salt (D436453), which is a labelled analogue of Diclofenac Sodium Salt (D436450).

Purification Methods

Crystallise the ester from MeOH or glacial acetic acid. [Beilstein 11 H 99, 11 II 47, 11 III 200, 6 IV 271.]

Upstream product

• 110-86-1 pyridine 
• 98-59-9 p-toluenesulfonyl chloride 
• 108-95-2 phenol 
• 78497-67-3 2,4-dinitro-6-methylphenyl p-toluenesulfonate 
• 139-02-6 sodium phenoxide 
• 71-43-2 benzene 
• 25491-50-3 thallous phenoxide 
• 4973-66-4 methyl thiotosylate 
• 102-09-0 bis(phenyl) carbonate 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 87732-47-6 1,4-Dihydro-1-(4-methylphenylsulfonyl)-4-<(4-methylphenylsulfonyl)phenylmethylen>pyridin 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 108-86-1 bromobenzene 
• 108-88-3 toluene 

Downstream Products

• 21784-96-3 n-butyl 4-methylphenyl sulfide 
• 91638-69-6 3-methylbutyl p-tolyl sulfide 
• 91485-21-1 1-<(p-methylphenyl)sulfonyl>-3-methylbutane 
• 7402-77-9 4-tosylphenol 
• 32569-84-9 ethoxyethynylbenzene 
• 640-57-3 phenyltolylsulfone 
• 1153-45-3 4-nitrophenyl 4-methylbenzenesulfonate 
• 16634-83-6 2-nitro-toluene-4-sulfonic acid-(4-nitro-phenyl ester) 
• 100-29-8 1-ethoxy-4-nitrobenzene 
• 1216-95-1 p-tolyl p-methoxyphenyl sulfone 
• 108-95-2 phenol 
• 1072-16-8 2,7-dimethyloctane 
• 599-66-6 bis(4-methylphenyl) sulfone 
• 13249-99-5 α-naphthyl p-methylphenyl sulphone 

Relevant articles and documents

Unprecedented regioselective tosylation studies of 2-ene 4,5,6,7-polyol derived from d-ribose

[DMAPTs]+Cl- was employed as a new facile unprecedented regioselective tosylation procedure for 2-ene 4,5,6,7-polyol derived from d-ribose involving chemoselective ditosylation and regioselective allylic tosyl hydrolysis upon work up with sat. NaCl (brine) solution in a single operation by minimizing the side products obtained under classical regioselective tosylation. The same reagent was also employed for rapid quantitative base free tosylation of aniline, phenol, and 2-naphthol. A tentative mechanism for the afore said regioselective tosylation was also proposed.

Identification of organophosphorus simulants for the development of next-generation detection technologies

Organophosphorus (OP) chemical warfare agents (CWAs) represent an ongoing threat but the understandable widespread prohibition of their use places limitations on the development of technologies to counter the effects of any OP CWA release. Herein, we describe new, accessible methods for the identification of appropriate molecular simulants to mimic the hydrogen bond accepting capacity of the PO moiety, common to every member of this class of CWAs. Using the predictive methodologies developed herein, we have identified OP CWA hydrogen bond acceptor simulants for soman and sarin. It is hoped that the effective use of these physical property specific simulants will aid future countermeasure developments.

Nickel-Catalyzed Photodehalogenation of Aryl Bromides

Herein, we describe a Ni-catalyzed photodehalogenation of aryl bromides under visible-light irradiation that utilizes tetrahydrofuran as hydrogen source. The protocol obviates the need for exogeneous amine reductants or photocatalysts and is characterized by its simplicity and broad scope, including challenging substrate combinations.

Quantum Dot-Catalyzed Photoreductive Removal of Sulfonyl-Based Protecting Groups

This Communication describes the use of CuInS2/ZnS quantum dots (QDs) as photocatalysts for the reductive deprotection of aryl sulfonyl-protected phenols. For a series of aryl sulfonates with electron-withdrawing substituents, the rate of deprotection for the corresponding phenyl aryl sulfonates increases with decreasing electrochemical potential for the two electron transfers within the catalytic cycle. The rate of deprotection for a substrate that contains a carboxylic acid, a known QD-binding group, is accelerated by more than a factor of ten from that expected from the electrochemical potential for the transformation, a result that suggests that formation of metastable electron donor–acceptor complexes provides a significant kinetic advantage. This deprotection method does not perturb the common NHBoc or toluenesulfonyl protecting groups and, as demonstrated with an estrone substrate, does not perturb proximate ketones, which are generally vulnerable to many chemical reduction methods used for this class of reactions.