4124-41-8

Basic information

• Product Name: P-Toluenesulfonic anhydride
• Synonyms: P-TOLUENESULFONIC ANHYDRIDE;P-TOLUENESULPHONIC ANHYDRIDE;TOLUENE-4-SULFONIC ANHYDRIDE;1,3-BIS(4-METHYLPHENYL)-1,1,3,3-TETRAOXO-1LAMBDA6,3LAMBDA6-DITHIOXANE;4-TOLUENESULPHONIC ANHYDRIDE;Tosic anhydride;toluene-p-sulphonic anhydride;4-Toluenesulphonic acid anhydride
• CAS NO: 4124-41-8
• Molecular Formula: C₁₄H₁₄O₅S₂
• Molecular Weight: 326.39
• EINECS: 223-926-9
• Product Categories: Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;Organic Building Blocks;Sulfonic/Sulfinic Acid Anhydrides;Sulfur Compounds;Sulfonic/Sulfinic Acid Anhydrides;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;Pyridines
• Mol File: 4124-41-8.mol
• Article Data: 22

Chemical Properties

• Melting Point: 121-127 °C(lit.)
• Boiling Point: 478 °C at 760 mmHg
• Flash Point: 242.9 °C
• Appearance: Off-white to gray/Powder, Crystals and/or Chunks
• Density: 1.361 g/cm³
• Vapor Pressure: 7.72E-09mmHg at 25°C
• Refractive Index: 1.582
• Storage Temp.: 2-8°C
• Sensitive: Moisture Sensitive
• BRN: 2223702
• CAS DataBase Reference: P-Toluenesulfonic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: P-Toluenesulfonic anhydride(4124-41-8)
• EPA Substance Registry System: P-Toluenesulfonic anhydride(4124-41-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2585 8/PG 3
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 4124-41-8(Hazardous Substances Data)

Usage

Chemical Properties

Off-white to cream powder

Uses

p-Toluenesulfonic anhydride has been employed as reagent in palladium-catalyzed allylic alkenylation of allylic alcohols with n-butyl acrylate.

General Description

p-Toluenesulfonic anhydride acts as electrophilic species and activates 2-deoxy-sugar hemiacetals in situ, which reacts stereoselectively with nucleophilic acceptors to afford β-anomers.

InChI:InChI=1/C14H14O5S2/c1-11-3-7-13(8-4-11)20(15,16)19-21(17,18)14-9-5-12(2)6-10-14/h3-10H,1-2H3

Upstream product

• 58010-17-6 6-dichloromethyl-1,3,2,4,5-dioxadithiazine 2,2,4,4-tetroxide 
• 788-86-3 p-tolylsulfinyl p-tolyl sulfone 
• 68819-94-3 p-tolyl benzeneselenosulfonate 
• 13079-28-2 benzoic toluene-p-sulphonic anhydride 
• 104-15-4 toluene-4-sulfonic acid 
• 80-48-8 methyl p-toluene sulfonate 
• 108-88-3 toluene 
• 1950-78-3 p-toluenesulfonyl iodide 
• 94-36-0 dibenzoyl peroxide 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 98-59-9 p-toluenesulfonyl chloride 
• 55865-38-8 diethylaminobis(trifluoromethyl)phosphine 
• 38542-71-1 N-methylpyridinium p-toluenesulfonate 
• 75-36-5 acetyl chloride 

Downstream Products

• 106342-08-9 21-p-toluenesulfonate of 17α,21-dihydroxy-4-pregnene-3,20-dione 
• 103276-85-3 1-dibenzylamino-2-(toluene-4-sulfonyloxy)-ethane; toluene-4-sulfonate 
• 10371-42-3 S-(4-methylphenyl) thiobenzoate 
• 128917-53-3 ethyl (Z)4,4-dimethyl-3-(p-toluene-sulphonyloxy)-2-pentenoate 
• 128917-56-6 tert-butyl (Z)4-phenyl-3-(p-toluene-sulphonyloxy)-2-butenoate 
• 76454-62-1 Toluene-4-sulfonic acid 2-cyano-adamantan-2-yl ester 
• 123331-71-5 <(1R*)-3-<(1S*,4S*,5R*)-4,5-Dimethyl-6-methylenspirooctan-2,2'-<1,3>dioxolan>-5-yl>-1-methylpropyl>-p-toluolsulfonat 
• 123408-87-7 <(1R*)-3-<(1R*,4R*,5S*)-4,5-Dimethyl-6-methylenspirooctan-2,2'-<1,3>dioxolan>-5-yl>-1-methylpropyl>-p-toluolsulfonat 
• 124288-83-1 1,1-dimethylethyl -9(S)-<<(4-methylphenyl)sulfonyl>amino>-2,3-O-(1-methylethylidene)-β-D-allo-decofuranosid>uronate 
• 124288-99-9 (2S,5S)-6-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(toluene-4-sulfonylamino)-5-(toluene-4-sulfonyloxy)-hexanoic acid tert-butyl ester 
• 128917-52-2 tert-butyl (Z)4-methyl-3-(p-toluene-sulphonyloxy)-2-butenoate 
• 128917-54-4 tert-butyl (Z)3-c-hexyl-3-(p-toluene-sulphonyloxy)-2-propenoate 
• 131043-64-6 Toluene-4-sulfonic acid 1-methyl-dec-2-ynyl ester 
• 133707-25-2 c-3-<3-(tert-butyldiphenylsilyloxy)-2-O-(p-tolylsulfonyl)-1,4-bis-O-trimethylsilylprop-1-ynyl>-cyclohexane-r-1,t-2,c-4-triol 

Relevant articles and documents

New carboxymethyl cellulose tosylate with low biodeterioration

Microbial biodegradation and biodeterioration of cellulose based thickeners is a serious problem in industry. A new tosylic ester of carboxymethyl cellulose (TsCMC) was prepared with anhydride of p-toluensulphonic acid. The TsCMC has improved rheological properties, higher viscosity and pseudoplasticity, superior emulsification properties and decreased wettability compared to parental CMC. The biodeterioration of TsCMC was significantly reduced compared to parental CMC or other commercially used modified cellulose thickeners in water based paint industry. Improved rheological properties combined with low biodeterioration make TsCMC a promising new material for industrial applications with a potential to reduce the use of hazardous antimicrobial agents.

An improved synthesis of 6-O-monotosyl-6-deoxy-β-cyclodextrin

Addition of p-toluenesulfonic anhydride (Ts2O) to β-cyclodextrin (CD) in water, followed by treatment with 10% aqueous NaOH solution for 10 min and removal of excess Ts2O by filtration, gave mono-6-deoxy-6-(O-p- toluenesulfonyl)-CD (1) in 61% yield.

Efficient modification of PAMAM G1 dendrimer surface with β-cyclodextrin units by CuAAC: Impact on the water solubility and cytotoxicity

The toxicity of the poly(amidoamine) dendrimers (PAMAM) caused by the peripheral amino groups has been a limitation for their use as drug carriers in clinical applications. In this work, we completely modified the periphery of PAMAM dendrimer generation 1 (PAMAM G1) with β-cyclodextrin (β-CD) units through the Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC) to obtain the PAMAM G1-β-CD dendrimer with high yield. The PAMAM G1-β-CD was characterized by 1H- and 13C-NMR and mass spectrometry studies. Moreover, the PAMAM G1-β-CD dendrimer showed remarkably higher water solubility than native β-CD. Finally, we studied the toxicity of PAMAM G1-β-CD dendrimer in four different cell lines, human breast cancer cells (MCF-7 and MDA-MB-231), human cervical adenocarcinoma cancer cells (HeLa) and pig kidney epithelial cells (LLC-PK1). The PAMAM G1-β-CD dendrimer did not present any cytotoxicity in cell lines tested which shows the potentiality of this new class of dendrimers.

Process for the preparation of aromatic sulfonic anhydrides

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