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

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

Uses

1. Used in Organic Synthesis:
P-Toluenesulfonic anhydride is used as a reagent for activating 2-deoxy-sugar hemiacetals in situ, which then react stereoselectively with nucleophilic acceptors to afford β-anomers. This application is particularly useful in the synthesis of complex organic molecules and pharmaceutical compounds.
2. Used in Palladium-Catalyzed Allylic Alkenylation:
In the field of organic chemistry, P-Toluenesulfonic anhydride is employed as a reagent in palladium-catalyzed allylic alkenylation of allylic alcohols with n-butyl acrylate. This reaction is an important method for the formation of carbon-carbon bonds and is widely used in the synthesis of various organic compounds, including pharmaceuticals and natural products.
3. Used in Other Chemical Reactions:
Due to its electrophilic nature, P-Toluenesulfonic anhydride can be utilized in various other chemical reactions, such as esterification, acylation, and dehydration processes. It serves as a versatile reagent in the synthesis of a wide range of organic compounds, making it valuable in the chemical and pharmaceutical industries.

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

• 104-15-4 toluene-4-sulfonic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 103-19-5 di(p-tolyl) disulfide 
• 1950-78-3 p-toluenesulfonyl iodide 
• 16836-95-6 silver(I) 4-methylbenzenesulfonate 
• 58010-14-3 6-trichloromethyl-1,3,2,4,5-dioxadithiazine 2,2,4,4-tetroxide 
• 108-88-3 toluene 
• 58010-17-6 6-dichloromethyl-1,3,2,4,5-dioxadithiazine 2,2,4,4-tetroxide 
• 78-67-1 2,2'-azobis(isobutyronitrile) 
• 19481-79-9 2-iodo-2-methylpropanenitrile 
• 788-86-3 p-tolylsulfinyl p-tolyl sulfone 
• 68819-94-3 p-tolyl benzeneselenosulfonate 
• 13079-28-2 benzoic toluene-p-sulphonic anhydride 
• 80-48-8 methyl p-toluene sulfonate 

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 
• 2943-42-2 di(4-methyl)phenylthiosulfonate 
• 70774-92-4 methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside 
• 4724-56-5 1,4-ditosyloxybutane 
• 38238-81-2 2-[(4-Nitro-phenyl)-(toluene-4-sulfonyloxy)-methylene]-malonic acid diethyl ester 
• 32244-65-8 2.2-Di-t-butoxycarbonyl-1-p-tolylvinyl-toluol-p-sulfonat 
• 32244-71-6 2.2-Dicarboxy-1-p-methoxyphenylvinyl-toluol-p-sulfonat 
• 10371-42-3 S-(4-methylphenyl) thiobenzoate 
• 51804-15-0 4-carboxyphenyl 4-methylbenzenesulfonate 
• 128917-53-3 ethyl (Z)4,4-dimethyl-3-(p-toluene-sulphonyloxy)-2-pentenoate 
• 17872-98-9 4-Methyl-1-benzolsulfonsaeure-trimethylsilylester 
• 97730-07-9 O,O'-diethylphosphoric 4-methylbenzenesulfonic anhydride 
• 128917-56-6 tert-butyl (Z)4-phenyl-3-(p-toluene-sulphonyloxy)-2-butenoate 

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.

First class of phosphorus dendritic compounds containing β-cyclodextrin units in the periphery prepared by CuAAC

A new class of phosphorus dendritic compounds (PDCs) having a cyclotriphosphazene (P3N3) core and decorated with six β-cyclodextrin (βCD) units, named P3N3-[O-C6H4-O-(CH2)n-βCD]6, where n = 3 or 4 was designed, and the synthesis was performed using copper (I) catalyzed alkyne-azide cycloaddition (CuAAC). To obtain the complete substitution of the P3N3, two linkers consisting of an aromatic ring and an aliphatic chain of two different lengths were assessed. We found that, with both linkers, the total modification of the periphery was achieved. The two new obtained dendritic compounds presented a considerably high water solubility (>1 g/mL). The compounds comprised in this new class of PDCs are potential drug carrier candidates, since the conjugation of the βCD units to the P3N3 core through the primary face will not only serve as surface cover but, also, provide them the faculty to encapsulate various drugs inside the βCDs cavities.

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.

Sulfonylation of aromatic compounds with methyl p-toluenesulfonate as a sulfonylating precursor

We have developed Friedel-Crafts (FC) sulfonylation of aromatic compounds with methyl p-toluenesulfonate as a sulfonylating precursor. In this procedure, methyl p-toluenesulfonate was treated and activated with pyridine to produce N-methylpyridinium p-toluenesulfonate as a sulfonylation reagent. Reactivity of this salt for the sulfonylation of mesitylene was investigated in the presence of three different promoters, such as triflic anhydride, dimethylsulfide ditriflate, and triphenylphosphine ditriflate (TPPD). All of the promoters show chemoselectivity and among them, TPPD presents a chemoselectivity in FC sulfonylation. Iranian Chemical Society 2012.

Gas-phase catalytic Beckmann rearrangement over crystalline BPO4 of dehydration ability

The crystalline BPO4 with a P/B ratio around 1.5 prepared by dehydration of boric and phosphoric acid was found to be an effective heterogeneous catalyst for the gas-phase Beckmann rearrangement of cyclohexanone oxime to ε-caprolactam. Copyright

SYNTHESIS OF STERICALLY HINDERED SECONDARY AMINOETHER ALCOHOLS

Severely sterically hindered secondary aminoether alcohols are prepared by reacting organic carboxylic, organic carboxylic acid halides, acid anhydrides or a ketene with an alkyl, alkaryl or alkylhalo sulfonate to yield a sulfonic. Carboxylic anhydride compound which is then reacted with a dioxane to cleave the ring of the dioxane, yielding a cleavage product which cleavage product is then aminated with an alkylamine and hydrolyzed with base to yield the severely sterically hindered secondary aminoether alcohol.

Stable phosphinous acids

The electronic properties of organyl element compounds are strongly influenced by the electronic characteristics of the organic substituents. The bonding of two CF3 groups to a phosphorus atom effects a drastically decreased basicity. That is the phosphorus atom is the least basic centre in the compound (CF3)2POH. This compound, synthesized in 1960 by Burg and Griffiths, is the only known example of a phosphinous acid, although there should be a general interest in this class of compounds. However, only a few investigations have been reported which may be explained by the tedious and risky synthesis. In this paper a safe one step and high yield synthesis of (CF3)2POH is described. The compound (C6F 5)2POH, originally claimed as a phosphinous acid, is proved to exist at room temperature exclusively in the tautomeric oxide form. (C6F5)2P(O)H crystallizes in the triclinic space group P1? (no. 2) with a 992.9(1) pm; b 1501.9(2) pm; c 1539.4(2) pm; α 117.48(1)°; β 100.39(1)°; γ 96.02(1)° and Z 6. Quantum chemical investigations prove the electron withdrawing effect of s-triazinyl groups (1,3,5-triazin-4-yl derivatives) to be much stronger than that of pentafluorophenyl groups. Quantum chemical calculations at the B3PW91/6-311G(3d,p) level of theory predict for the bis(s-triazinyl) derivative (C3N3H2)2POH the phosphinous acid isomer to be favored by ΔEZP = 22 kJ/mol in relation to the corresponding phosphane oxide isomer. The phosphinous acid (CF3) 2POH (Cs symmetry) is favored at the same level of theory by about ΔEZP = 14 kJ/mol compared with the phosphane oxide structure (Cs symmetry).

Process for functionalising a phenolic compound carrying an electron-donating group

The invention concerns a method for functionalizing a phenolic compound bearing an electron-donor group, in said group para position, inter alia a method for the amidoalkylation of a phenolic compound bearing an electron-donor group, and more particularly, a phenolic compound bearing an electron-donor group preferably, in the hydroxyl group ortho position. The method for functionalizing in para position with respect to an electron-donor group carried by a phenolic compound is characterised in that the phenolic compound bearing an electron-donor group is subjected to the following steps: a first step which consists of protecting the hydroxyl group in the form of a sulphonic ester function; a second step which consists in reacting the protected phenolic compound with an electrophilic reagent; optionally, a third step deprotecting the hydroxyl group.