18991-39-4

Usage

Uses

Used in Pharmaceutical Industry:
4-Methyl Thio Benzyl Cyanide is used as a raw material for the synthesis of organic compounds, serving as a key intermediate in the development of new drugs. Its unique chemical structure contributes to the creation of pharmaceutical agents with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Methyl Thio Benzyl Cyanide is employed as a precursor in the production of pesticides. Its chemical properties allow for the formulation of effective pest control solutions, enhancing crop protection and yield.
Used as a Flavor and Fragrance Ingredient:
4-Methyl Thio Benzyl Cyanide is utilized in the flavor and fragrance industry, capitalizing on its strong odor to create distinctive scents and tastes for various consumer products, including food, beverages, and perfumes.
It is crucial to handle 4-Methyl Thio Benzyl Cyanide with care due to its potential hazards if not used properly, ensuring safety in its applications across different industries.

InChI:InChI=1/C9H9NS/c1-8-2-4-9(5-3-8)6-11-7-10/h2-5H,6H2,1H3

Upstream product

• 83319-09-9 C₂₆H₂₄NS⁽¹⁺⁾*CNS^(1-) 
• 333-20-0 potassium thioacyanate 
• 104-82-5 4-Methylbenzyl chloride 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 104-81-4 4-Methylbenzyl bromide 
• 592-85-8 mercury(II) thiocyanate 
• 3694-46-0 p-methylbenzyl isothiocyanate 
• 1147550-11-5 ammonium thiocyanate 
• 89200-92-0 trimethyl(4-methylbenzyloxy)silane 
• 557-42-6 zinc(II) thiocyanate 
• 540-72-7 sodium thiocyanide 
• 589-18-4 4-Methylbenzyl alcohol 
• 106-42-3 para-xylene 
• 76950-78-2 1-(4-Methyl-benzyl)-2-methylsulfanyl-4,6-diphenyl-pyridinium; iodide 

Downstream Products

• 20193-94-6 bis-(4-methyl-benzyl)-disulfide 
• 35278-95-6 N,N-piperidyl-1-p-tolylmethanamine 
• 22205-64-7 piperidine thiocyanate 
• 5023-65-4 4-methylbenzyl phenyl sulfide 
• 85372-19-6 4-methylbenzyl phenyl disulfide 
• 882-33-7 diphenyldisulfane 
• 5925-57-5 methyl p-methylbenzyl thioether 
• 17271-89-5 4-methylphenylmethylazide 
• 34306-01-9 N-ethyl-N-(4-methylbenzyl)ethanamine 
• 3694-46-0 p-methylbenzyl isothiocyanate 
• 721-45-9 1,4-dimethyl-2-(4-methylbenzyl)benzene 
• 210626-06-5 1H-3-iodo-4-(4-methylbenzylthio)-6-methylbenzothiopyran 
• 210625-99-3 bis(4-methylbenzylthio)acetylene 
• 104-82-5 4-Methylbenzyl chloride 

Relevant academic research and scientific papers

AIBN-initiated direct thiocyanation of benzylic sp3C-H with: N -thiocyanatosaccharin

Direct thiocyanations of benzylic compounds have been implemented. Here, a new strategy, involving a free radical reaction pathway initiated by AIBN, was used to construct the benzylic sp3 C-SCN bond. In this way, the disadvantage of other strategies involving introducing leaving groups in advance to synthesize benzyl thiocyanate compounds was overcome. The currently developed protocol also involved the use of readily available raw materials and resulted in high product yields (up to 100%), both being great advantages for synthesizing benzyl thiocyanates.

Sulfuryl Fluoride Promoted Thiocyanation of Alcohols: A Practical Method for Preparing Thiocyanates

A novel SO 2F 2-promoted thiocyanation method for the one-step synthesis of thiocyanates through C-O bond cleavage of readily available alcohols with ammonium thiocyanate as the thiocyanating agent was developed. The method avoids the use of additional catalyst, and a variety of (hetero)arene, alkene and aliphatic alcohols reacted with high efficiency in ethyl acetate under mild conditions to afford the corresponding thiocyanates in excellent to quantitative yields with broad functional-group compatibility.

PEG-DIL-based MnCl42?: A novel phase transfer catalyst for nucleophilic substitution reactions of benzyl halides

Poly(ethylene glycol) dicationic ionic liquid-based MnCl42? was prepared by nucleophilic substitution of poly(ethylene glycol) dichloride with methylimidazole followed by reaction with MnCl2. The structural properties of the catalyst were systematically investigated using Fourier transform infrared, UV–visible and Raman spectra and thermogravimetric analysis. The application of this catalyst allows the synthesis of a variety of benzyl thiocyanates and azides in high yield under reflux conditions in water. The main advantages of this method are its easy nature, rapidity, environmental benignity and high yields.

One-pot synthesis of (ethoxycarbonyl)difluoromethylthioethers from thiocyanate sodium and ethyl 2-(trimethylsilyl)-2,2-difluoroacetate (TMS-CF2CO2Et)

An efficient one-pot cascade methodology for the synthesis of (ethoxycarbonyl)difluoromethyl thioethers is described. Benzyl, allyl, alkyl halides or diazonium salts as the starting materials together with thiocyanate sodium and TMS-CF2CO2Et in the presence of CsF or NaOAc afford a variety of the fluoroalkylthiolated products in moderate to good yields.

Microwave-assisted synthesis of alkyl thiocyanates

Microwave irradiation accelerated the reaction of t-alkyl, allyl, and benzyl halides with Zn(SCN)2 to afford thiocyanates in excellent yields and high selectivity with the formation of isothiocyanates only in minor proportions. Because thiocyanates are stable intermediates to thiols, the method also affords facile access to corresponding thiols.

A convenient, rapid, and general synthesis of α-oxo thiocyanates using clay supported ammonium thiocyanate

A very rapid, convenient, and general method for the synthesis of α-oxo thiocyanates has been described by using clay supported ammonium thiocyanate. The procedure avoids the use of additional catalyst, solvent, aqueous work-up and the yields are high. Moreover, the method is applicable for a variety of aryl, heteroaryl, alkyl α-halo carbonyls, β-keto tosylates, α-halo β-dicarbonyl, α-tosyl, β-dicarbonyl, alkyl halide, and alkyl tosylates.

2-Hydroxy-N,N,N-tributylethanaminium thiocyanate as solvent and reagent for the preparation of alkyl thiocyanates

2-Hydroxy-N,N,N-tributylethanaminium thiocyanate was utilized as both solvent and reagent for the conversion of alkyl halides to the corresponding alkyl thiocyanates in good yields under mild conditions.

Efficient conversion of silyl ethers to thiocyanates with Ph3P(SCN)2

A new and efficient method for the conversion of primary and secondary alkyl, aryl, allyl and benzyl silyl ethers to their corresponding thiocyanates by in-situ generation of Ph3P(SCN)2 is described. The reactions occur immediately at room temperature and provide high to excellent yields of thiocyantes.

Versatile route to functionalized 1H-2-benzothiopyrans and 1H-2- naphthothiopyrans by electrophilic cyclization of Bis(arylmethylthio)acetylenes: 2-Benzo- and 2-naphthothiopyrylium salts

Substituted 1H-2-benzothiopyrans find applications as pharmaceutically active compounds or synthons for more complex sulfur heterocycles. However, restricted variability in their synthesis limits the application for research or industrial purposes. To develop a direct and fast route to substituted and functionalized 1H-2-benzothiopyrans, we investigated the ring closure of symmetrical bis(arylmethylthio)acetylenes with iodine monochloride or bromine. This facile reaction yielded 1H-3-halo-4-arylmethylthio-2-benzo- and 2-naphthothiopyrans via postulated vinyl cations in yields of 47-86%. Substituted 2-benzo- and 2-naphthothiopyrylium salts were prepared by hydride abstraction with triphenylcarbenium tetrafluoroborate from the products, further enhancing the synthetic potential of the found cyclization reaction.

Photolysis of Vinyl Halides. Reaction of Photogenerated Vinyl Cations with Cyanate and Thiocyanate Ions

The title reaction was conducted in a two-phase system of dichloromethane and water using a tetrabutylammonium halide as a phase-transfer catalyst.The reaction of the photogenerated arylvinyl cation with cyanate ion gave only isoquinolone derivatives, whereas the reaction with thiocyanate ion afforded products derived from S attack, vinyl thiocyanates, and products derived from N attack, vinyl isothiocyanates or thioisoquinolones.The ambident nature of thiocyanate ion is compared with the reaction of benzyl bromides.