26908-82-7

Basic information

• Product Name: (4-Methylphenyl)sulfonyl acetate
• Synonyms: Acetic Acid, Anhydride With P-Toluenesulfonic Acid;Acetic P-Toluenesulfonic Anhydride;(4-METHYLPHENYL)SULFONYL ACETATE;UOAJUPONZOXFNX-UHFFFAOYSA-N
• CAS NO: 26908-82-7
• Molecular Formula: C₉H₁₀O₄S
• Molecular Weight: 214.24
• Mol File: 26908-82-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 325.7 °C at 760 mmHg
• Flash Point: 150.8 °C
• Appearance: /
• Density: 1.279 g/cm³
• Vapor Pressure: 0.000227mmHg at 25°C
• Refractive Index: 1.524
• CAS DataBase Reference: (4-Methylphenyl)sulfonyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (4-Methylphenyl)sulfonyl acetate(26908-82-7)
• EPA Substance Registry System: (4-Methylphenyl)sulfonyl acetate(26908-82-7)

Safety Data

• Hazardous Substances Data: 26908-82-7(Hazardous Substances Data)

Usage

Purification Methods

The most likely impurity is p-toluenesulfonic acid (could be up to 10%). This can be removed by dissolving it in dry Et2O and cooling until the anhydride crystallises out. It decomposes on heating; below ~130o it gives the disulfonic anhydride and above ~130o polymers are formed, but it can be distilled in a vacuum if it is free of acid. It is used for cleaving ethers [Prep, IR, NMR: Karger & Mazur J Org Chem 36 528, Karger & Mazur J Org Chem 36 532 1971]. [Beilstein 11 III 255.]

InChI:InChI=1/C9H10O4S/c1-7-3-5-9(6-4-7)14(11,12)13-8(2)10/h3-6H,1-2H3

Upstream product

• 104-15-4 toluene-4-sulfonic acid 
• 75-36-5 acetyl chloride 
• 16836-95-6 silver(I) 4-methylbenzenesulfonate 
• 10534-59-5 tetrabutylammonium acetate 
• 98-59-9 p-toluenesulfonyl chloride 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 

Downstream Products

• 19859-06-4 p-Toluolsulfonsaeure-(4-acetoxy-butylester) 
• 26923-87-5 2-acetoxyethyl-2'-tosyloxyethyl ether 
• 34553-05-4 Acetic acid (Z)-4-(toluene-4-sulfonyloxy)-but-2-enyl ester 
• 103-84-4 Acetanilid 
• 61000-04-2 4,4'-Dimethoxy-β-methylchalcon 
• 147030-98-6 1-(4-phenylfuran-2-yl)ethanone 
• 108-21-4 Isopropyl acetate 
• 1118-69-0 N-isopropylacetamide 
• 1117-77-7 methyl N-acetylglycinate 
• 141-78-6 ethyl acetate 
• 778-28-9 butyl para-toluenesulfonate 
• 599-91-7 propyl tosylate 
• 2307-69-9 toluene-4-sulfonic acid isopropyl ester 
• 19859-07-5 p-Toluolsulfonsaeure-(5-acetoxy-pentyl-2)-ester 

Relevant articles and documents

Correlation of the rates of solvolysis of acetic p-toluenesulfonic anhydride (acetyl p-toluenesulfonate) and a comparison with acetyl halides

The specific rates of solvolysis of acetyl p-toluenesulfonate have been measured by a rapid-response conductivity technique at temperatures in the temperature range of -10 to -55 °C. For 13 solvents at -39.6 °C, an extended Grunwald-Winstein equation correlation led to sensitivities to changes in solvent nucleophilicity of 0.56 and to changes in solvent ionizing power of 0.61. In 89.1% acetone at -20 °C, the comparison with acetyl bromide solvolysis led to a kOTs/kBr ratio of 1.4. In methanol and methanol-d at -39.6 °C, the solvent deuterium isotope effect k MeOH/kMeOD is 0.99. These results are consistent with an SNl reaction with appreciable nucleophilic solvation or an S N2 reaction with a loose transition state. These two approaches lead to similar structures for the transition state. A solution of the acetyl p-toluenesulfonate was conveniently prepared by the rapid reaction of acetyl chloride with silver p-toluenesulfonate in acetonitrile. Copyright 2013 John Wiley & Sons, Ltd. Correlation of the rates of solvolysis of acetic p-toluenesulfonic anhydride (acetyl p-toluenesulfonate) and a comparison with acetyl halides. Copyright

Syntheses of 1-substituted furan-fused 3-sulfolenes and their Diels-Alder reactions

The preparation of 1-substituted 4H,6H-dihydrothienofuran 5,5-dioxides and their intermolecular Diels-Alder reactions with typical dienophiles are described. 1-Acetyl-1d and 1-nitro-furansulfolene 1e were prepared by simple new methods.Acetyl and nitro substituents in the furan moiety did little to diminish its Diels-Alder reactivity relative to the corresponding furans.Furthermore, on reaction with dimethyl fumarate, 1-acetylfuransulfolene 1d acted like the corresponding 3,4-dimethylenefuran.

A novel and versatile route to mixed p-toluenesulphonic carboxylic anhydrides

A versatile route to the mixed p-toluenesulphonic carboxylic anhydrides (1) via the reaction of tetra-n-butylammonium carboxylate (2) with p-toluenesulphonyl chloride in a neutral medium is described.Some of the synthetic applications of the proposed method are described.