2082-64-6

Usage

General Description

4-CHLOROBENZYL THIOCYANATE, also known as p-Chlorobenzyl isothiocyanate, is a chemical compound consisting of a benzene ring with a chlorine substituent and a thiocyanate functional group. It is commonly used in the synthesis of pharmaceuticals and agrochemicals due to its antimicrobial and fungicidal properties. 4-CHLOROBENZYL THIOCYANATE has been studied for its potential in inhibiting the growth of certain cancer cells and may have a role in cancer therapy. Additionally, it has shown potential as a building block for the synthesis of organic compounds and in material science for the creation of polymer composites. However, it is important to handle 4-CHLOROBENZYL THIOCYANATE with caution as it can be toxic and irritating to the eyes, skin, and respiratory system.

InChI:InChI=1/C8H6ClNS/c9-8-3-1-7(2-4-8)5-11-6-10/h1-4H,5H2

Upstream product

• 333-20-0 potassium thioacyanate 
• 622-95-7 4-chlorobenzyl bromide 
• 1147550-11-5 ammonium thiocyanate 
• 873-76-7 para-Chlorobenzyl alcohol 
• 14856-74-7 4-chlorobenzyltrimethylsilyl ether 
• 18484-03-2 2-(4-chlorobenzyloxy)tetrahydro-2H-pyran 
• 163276-49-1 1-thiocyanatopyrrolidine-2,5-dione 
• 104-88-1 4-chlorobenzaldehyde 
• 540-72-7 sodium thiocyanide 
• 6258-66-8 (4-chlorophenyl)methanethiol 
• 106-43-4 para-chlorotoluene 
• 76950-79-3 1-(4-Chloro-benzyl)-2-methylsulfanyl-4,6-diphenyl-pyridinium; iodide 
• 83318-11-0 C₂₅H₂₁ClNS⁽¹⁺⁾*CNS^(1-) 

Downstream Products

• 52115-38-5 7-chloro-2-(4-chloro-benzylsulfanyl)-pyrano[3,4-e][1,3]oxazine-4,5-dione 
• 3694-45-9 4-chlorobenzylisothiocyanate 
• 725-41-7 4-chlorobenzyl piperidine-1-carbodithioate 
• 1429397-46-5 C₁₈H₁₅ClS₂ 
• 23566-17-8 bis(4-chlorobenzyl)disulfide 
• 102548-57-2 1-((naphthalene-1-yl)methyl)-2-((naphthalene-5-yl)methyl)disulfane 
• 882508-98-7 N-(4-Chlorobenzyl)-N'-{4-chloro-2-[(4-ethoxyphenyl)amino]phenyl}thiourea 

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.

Direct Photocatalytic S-H Bond Cyanation with Green cN Source

Herein we report a novel C-S bond cleavage and reconstruction strategy for the synthesis of thiocyanates through direct photocatalytic S-H bond cyanation from thiols and inorganic thiocyanate salts. In our strategy, the unprecedented example of cutting off C-S bond of SCN- to deliver the green CN sources is demonstrated. This transformation features nontoxic and inexpensive CN sources, available starting materials, metal-/base-/ligand-/peroxide-free, high step economy and mild conditions. It leads to the construction of various thiocyanates and some medicinally and biologically active thiocyanate-containing molecules.

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.

2,4,4,6-Tetrabromo-2,5-cyclohexadienone as an efficient reagent for phosphine-free electrophilic transformation of alcohols and epoxides

In this study, 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TABCO) was prepared and used successfully as a stable phosphine-free reagent for the conversion of alcohols into alkyl thiocyanates and epoxides into 2-hydroxythiocyanates. The reactions seem to proceed via in situ generation of electrophilic sulfur species by reaction of NH4SCN and TABCO. This combined reagent worked well with both alcohols and epoxides in acetonitrile solvent and under solvent-free conditions.

A simple, one-pot and phosphine-free procedure for thiocyanation of alcohols Using N-(p-toluenesulfonyl) imidazole (TsIm)

An efficient, one-pot, phosphine-free thiocyanation of alcohols has been achieved utilising potassium thiocyanate and N-(p-toluenesulfonyl) imidazole (TsIm) as a coupling agent in the presence of triethylamine in anhydrous DMF at 70 °C. This method converts primary alcohols into the corresponding thiocyanates, without isomerisation to isothiocyanates, in good to excellent yields. A total of 17 thiocyananates were prepared, five of which are novel. Using one equivalent of KSCN, the method shows good selectivity in the thiocyanation of a primary alcohol in the presence of a secondary alcohol.

Chlorodiphenylphosphine as highly selective and efficient reagent for the conversion of alcohols, tetrahydropyranyl and silyl ethers to thiocyanates and isothiocyanates

(Equation present) A simple, highly selective and efficient method is described for the conversion of primary alcohols, tetrahydropyranyl and silyl ethers to thiocyanates by use of chlorodiphenylphosphine and ammonium thiocyanate. Secondary substrates produce both the two isomeric products, thiocyanate and isothiocyanate, while tertiary ones give isothiocyanates as the only products by this new method. In contrast to previously reported methods based on trivalent phosphorus for this transformation, the present method does not require an electrophile in the presence of trivalent phosphorus (ClPPh 2). The order of activity of these substrates is silyl ether> alcohol > tetrahydropyranyl ether. The present method not only interestingly distinguishes between primary, secondary and tertiary substrates but also converts them to the corresponding thiocyanates with excellent chemoselectivity in the presence of several other functional groups. 2014 Copyright Taylor & Francis Group, LLC.

2-Chloro-1-methylpyridinium iodide, an efficient reagent for the conversion of alcohols into alkyl thiocyanates both under solvent and solvent-free conditions

A new application of the Mukaiyama reagent for the simple phosphine-free conversion of alcohols into the corresponding alkyl thiocyanates is described. This transformation can be achieved either in acetonitrile or under solvent-free conditions and the products obtained in good to excellent yields. The solvent-free procedure described here is the first report on the solvent-free thiocyanation of alcohols.

Phosphine-free conversion of alcohols into alkyl thiocyanates using trichloroisocyanuric acid/NH4SCN

A convenient and efficient phosphine-free procedure for the one-pot conversion of primary, secondary and tertiary alcohols into the corresponding alkyl thiocyanates or alkyl isothiocyanates is described using trichloroisocyanuric acid/NH4SCN.

Selectfluor F-TEDA-BF4 mediated thiocyanation or isothiocyanation of alcohols by in situ generation of [+SCN] under heterogeneous and neutral conditions

A convenient approach for thiocyanation of alcohols has been developed using ammonium thiocyanate as thiocyanating agent in the presence of a catalytic amount of Selectfluor F-TEDA-BF4 in aqueous acetonitrile. In this method various alcohols generally afforded the corresponding thiocyanates or isothiocyanates directly in good to high yield under heterogeneous and neutral conditions.