1024-41-5

Basic information

• Product Name: BENZYL 4-TOLUENESULFONATE
• Synonyms: BENZYL 4-TOLUENESULFONATE;phenylmethyl 4-methylbenzenesulfonate
• CAS NO: 1024-41-5
• Molecular Formula: C₁₄H₁₄O₃S
• Molecular Weight: 262.32
• Product Categories: pharmacetical
• Mol File: 1024-41-5.mol
• Article Data: 33

Chemical Properties

• Melting Point: 58 °C
• Boiling Point: 412.7°Cat760mmHg
• Flash Point: 203.4°C
• Appearance: /
• Density: 1.222g/cm³
• Vapor Pressure: 1.21E-06mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: BENZYL 4-TOLUENESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 4-TOLUENESULFONATE(1024-41-5)
• EPA Substance Registry System: BENZYL 4-TOLUENESULFONATE(1024-41-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 1024-41-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 665, 1974 DOI: 10.1055/s-1974-34048

Purification Methods

Crystallise the ester from pet ether (b 40-60o), CHCl3/hexane or Et2O/*C6H6. Dry it in vacuo but NOT in a desiccator over CaCl2 as it causes hydrolysis of the ester. [Emmons & Ferris J Am Chem Soc 75 2257 1953, Beilstein 11 II 48, 11 III 207, 11 IV 273.]

InChI:InChI=1/C14H14O3S/c1-12-7-9-14(10-8-12)18(15,16)17-11-13-5-3-2-4-6-13/h2-10H,11H2,1H3

Upstream product

• 16836-95-6 silver(I) 4-methylbenzenesulfonate 
• 100-44-7 benzyl chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 104-15-4 toluene-4-sulfonic acid 
• 1927-62-4 tetrahydro-2-(benzyloxy)-2H-pyran 
• 14642-79-6 benzyloxy-trimethylsilane 
• 455-16-3 p-toluenesulfonyl fluoride 
• 64-19-7 acetic acid 
• 1112-02-3 d⁽³⁾-acetic acid 
• 1186-52-3 tetradeuterioacetic acid 
• 108-88-3 toluene 
• 4124-41-8 p-toluenesulfonylanhydride 

Downstream Products

• 946-80-5 (benzyloxy)benzene 
• 4560-41-2 2-benzyloxynitrobenzene 
• 32362-99-5 benzylthioacetate 
• 109451-46-9 toluene-4-sulfonic acid ; benzyloxy-dimethyl sulfonium-salt 
• 104-57-4 benzyl formate 
• 104-15-4 toluene-4-sulfonic acid 
• 6088-99-9 penta-1,3-diyne-1,5-diyldibenzene 
• 87576-34-9 Toluene-4-sulfonate3-benzyl-5-methyl-[1,2,3]thiadiazol-3-ium; 
• 15432-17-4 N₇-benzyl-7-azaindole 
• 152955-68-5 1-benzyl-1H-pyrrolo[2,3-b]-pyridine 
• 60290-17-7 N₁-benzyl-5-azaindole 
• 152955-67-4 N₆-benzyl-6-azaindole 
• 152955-66-3 N1-benzyl-6-azaindole 
• 87576-30-5 Toluene-4-sulfonate3-benzyl-5-phenyl-[1,2,3]thiadiazol-3-ium; 

Relevant articles and documents

Polymer enzyme conjugates as chiral ligands for sharpless dihydroxylation of alkenes in organic solvents

Conjugates of enzymes and poly(2-methyloxazoline) were used as organosoluble amphiphilic polymer nanocontainers for dissolving osmate, thereby converting the enzymes into organosoluble artificial metalloenzymes. These were shown to catalyze the dihydroxylation of different alkenes with high enantio-selectivity The highest selectivities, found for osmate complexed with laccase polymer-enzyme conjugates (PECs), even exceed those of classical Sharpless catalysts.

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Chemoselective and scalable preparation of alkyl tosylates under solvent-free conditions

The improved method for the efficient tosylation of alcohols has been reported using two procedures (A and B). Procedure A: methanol, ethanol, benzyl alcohols, and valuable ethylene glycols can be converted into their corresponding alkyl tosylates in very fast, simple, and efficient grinding method using potassium carbonate as solid base. Other primary and secondary alcohols need to add potassium hydroxide to reaction mixture (procedure B). High selectivity of tosylation was observed for these two procedures. Scale up ability was found in this method even in 100 mmol of substrate. The present method is the example of solid-state tosylation using tosyl chloride, and is a green chemical process due to solvent-free conditions.

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An efficient one-pot conversion of THP and TMS ethers to sulfonate esters using FeCl3-montmorillonite K-10 clay

Various tetrahydropyranyl and trimethylsilyl ethers are efficiently transformed into the corresponding sulfonate esters with sulfonyl chlorides in the presence of FeCl3-Montmorillonite K-10 clay.

Methanesulfinylation of Benzyl Halides with Dimethyl Sulfoxide

A phenyltrimethylammonium tribromide-mediated nucleophilic substitution/oxygen transformation reaction of benzyl halides with DMSO has been developed. In this transition-metal-free reaction, DMSO acts as not only a solvent but also a "S(O)Me" source, thus providing a convenient method for the efficient and direct synthesis of various benzyl methyl sulfoxides.

Ionic liquid brush as an efficient and reusable heterogeneous catalytic assembly for the tosylation of phenols and alcohols in neat water

A very efficient and reusable heterogeneous ionic liquid brush assembly was developed. The catalyst exhibits high catalytic activity for the tosylation of phenols and alcohols in neat water. Moreover, the catalyst shows outstanding stability and reusability, and it can be simply and effectively recovered and reused five times without noticeable loss of catalytic activity.