13287-49-5

Basic information

• Product Name: 4-NITROBENZYL THIOCYANATE
• Synonyms: Thiocyanic acid, (4-nitrophenyl)methyl ester;Thiocyanic acid, (p-nitrobenzyl) ester;Thiocyanic acid, 4-nitrobenzyl ester;thiocyanicacid,(4-nitrophenyl)methylester;thiocyanicacid,(p-nitrobenzyl)ester;thiocyanicacid,4-nitrobenzylester;P-NITROBENZYL THIOCYANATE;4-NITROBENZYL THIOCYANATE
• CAS NO: 13287-49-5
• Molecular Formula: C₈H₆N₂O₂S
• Molecular Weight: 194.21
• EINECS: 236-299-1
• Mol File: 13287-49-5.mol

Chemical Properties

• Melting Point: 83-85°C
• Boiling Point: 367.9°Cat760mmHg
• Flash Point: 176.3°C
• Appearance: /
• Density: 1.373g/cm³
• Vapor Pressure: 1.33E-05mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: 4-NITROBENZYL THIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITROBENZYL THIOCYANATE(13287-49-5)
• EPA Substance Registry System: 4-NITROBENZYL THIOCYANATE(13287-49-5)

Safety Data

• Statements: 20/22-32
• Safety Statements: 22-36/37
• RIDADR: 2811
• Hazardous Substances Data: 13287-49-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-NITROBENZYL THIOCYANATE is used as a synthetic intermediate for the production of various pharmaceuticals. Its reactivity allows for the creation of a wide range of drug compounds, contributing to the development of new medications and therapies.
Used in Agrochemical Industry:
In the agrochemical sector, 4-NITROBENZYL THIOCYANATE serves as a key intermediate in the synthesis of different agrochemicals. Its role in formulating effective pest control agents and other agricultural products highlights its importance in this industry.
Used in Research Applications:
4-NITROBENZYL THIOCYANATE is utilized in research settings for its potential to form various chemical derivatives. This makes it a valuable tool for scientists exploring new chemical reactions and developing innovative applications in both academic and industrial research.
Used in Industrial Applications:
Due to its reactivity and ability to form derivatives, 4-NITROBENZYL THIOCYANATE is employed in various industrial applications. Its use extends beyond pharmaceuticals and agrochemicals, finding relevance in the creation of specialty chemicals and other products that require its unique properties.

InChI:InChI=1/C8H6N2O2S/c9-6-13-5-7-1-3-8(4-2-7)10(11)12/h1-4H,5H2

Upstream product

• 3012-37-1 benzyl thiocyanate 
• 7697-37-2 nitric acid 
• 100-14-1 4-nitrobenzyl chloride 
• 151-50-8 potassium cyanide 
• 18483-99-3 2-(4-nitrobenzyloxy)tetrahydro-2H-pyran 
• 1147550-11-5 ammonium thiocyanate 
• 619-73-8 4-nitrobenzyl chloride 
• 333-20-0 potassium thioacyanate 
• 3674-54-2 tetrabutylammonium thiocyanate 
• 163276-49-1 1-thiocyanatopyrrolidine-2,5-dione 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 14856-73-6 4-nitrobenzyl trimethylsilyl ether 
• 540-72-7 sodium thiocyanide 
• 557-42-6 zinc(II) thiocyanate 

Downstream Products

• 99-99-0 1-methyl-4-nitrobenzene 
• 26060-30-0 4-nitrothiobenzamide 
• 60952-00-3 thiocarbamic acid S-(4-nitro-benzyl ester) 
• 1835-71-8 bis(4-nitrobenzyl) sulfide 
• 26798-33-4 (p-nitrophenyl)methanethiol 
• 119835-51-7 1,4-Bis-[5-(4-nitro-phenyl)-thiazol-2-yl]-piperazine 
• 105051-50-1 (4-Methoxy-phenyl)-[5-(4-nitro-phenyl)-thiazol-2-yl]-amine 
• 105051-48-7 4-[5-(4-Nitro-phenyl)-thiazol-2-yl]-morpholine 
• 105051-49-8 N-cyclohexyl-5-(4-nitrophenyl)-1,3-thiazol-2-amine 
• 105051-52-3 Methyl-[5-(4-nitro-phenyl)-thiazol-2-yl]-phenyl-amine 
• 105051-51-2 [5-(4-Nitro-phenyl)-thiazol-2-yl]-pyridin-3-yl-amine 
• 99941-56-7 [5-(4-Nitro-phenyl)-thiazol-2-yl]-phenyl-amine 
• 3694-47-1 1-(isothiocyanatomethyl)-4-nitrobenzene 
• 4025-75-6 (4-nitrophenyl)methanesulfonyl chloride 

Relevant articles and documents

Interfacial behavior of phase transfer catalysis of the reaction between potassium thiocyanate and p-nitrobenzyl bromide with crown ethers as catalysts

A very simple and novel method is devised to study the mechanism of phase transfer catalysis (PTC) for a nucleophilic substitution reaction between potassium thiocyanate and p-nitrobenzyl bromide (p-NB); the mechanism of the nucleophilic substitution reac

Modified Crown Ether Catalysis. 3. Structural Parameters Affecting Phase Transfer Catalysis by Crown Ethers and a Comparison of the Effectiveness of Crown Ethers to That of Other Phase Transfer Catalysts

Simple crown ethers and several series of substituted dibenzo and dicyclohexano crown ethers were used to catalyze two-phase nucleophilic substitution reactions.The rates of the reaction obeyed pseudo-first-order kinetics.Within the series of substituted

An ionic liquid supported on magnetite nanoparticles as an efficient heterogeneous catalyst for the synthesis of alkyl thiocyanates in water

The present study describes a convenient method to synthesize alkyl thiocyanates from alkyl halides with the use of a novel nanomagnetic-supported organocatalyst (MNP@PEG-ImCl). The new supported ionic liquid is fully characterized by field-emission scanning electron microscopy (FESEM), Fourier-transform infrared (FT-IR), energy dispersive X-ray analysis (EDAX), X-ray powder diffraction (XRD), transmission electron microscopy (TEM), vibrating sample magnetometry (VSM) as well as thermogravimetric analysis (TGA) techniques. It is noteworthy that we observed easy separation of the catalyst from the reaction mixture by a simple magnetic decantation and its reutilization many times without any appreciable loss of activities.

Method for preparing organic thiocyanide

The invention relates to a method for preparing organic thiocyanide. The method comprises the following steps: mixing a benzyl alcohol compound (I) as described in the specification, thiocyanate, an alkaline substance and an organic solvent, carrying out a reaction at 25-50 DEG C for 3-6 hours in an SO2F2 atmosphere, and carrying out after-treatment on a reaction solution to obtain organic thiocyanide (II) as described in the specification. According to the invention, cheap, easily available and environment-friendly SO2F2 is used as an accelerant to efficiently promote preparation of organic thiocyanide from alcohol and thiocyanate, so the step that halogen is introduced into a preset position of a molecular structure in advance in a traditional production process is omitted; and the method is applicable to a wide range of substrates, can prepare corresponding organic thiocyanide at a high yield, is simple in operation process, and is suitable for large-scale preparation.

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.

Potent anti-proliferative activities of organochalcogenocyanates towards breast cancer

The pharmacological importance, particularly the anti-cancer and chemopreventive potentials, of organochalcogen compounds has attracted wide research attention recently. Herein we describe the synthesis of a series of organochalcogenocyanates that have one or more selenocyanate or thiocyanate units in a single molecule. The anti-proliferative activity of these organochalcogenocyanates in different breast cancer cells shows that selenocyanates exhibit much higher anti-proliferative activities than thiocyanates in general. Our study reveals that the activity of benzyl selenocyanate (1, BSC) could be significantly enhanced by 4-nitro substitution (12), which was more selective towards triple-negative breast cancer cells (MDA-MB-231) over other ER+ breast cancer cells (MCF-7 and T-47D). Furthermore, to the best of our knowledge, this is the first report on the synthesis of compounds having more than two selenocyanate units with promising anti-proliferative activities. Our studies further indicate that the apoptotic activities of selenocyanates are associated with modulation of cellular morphology and cell cycle arrest at S-phase. Selenocyanates also inhibited cellular migration and exhibited weak antioxidant activities. An effective binding interaction of compound 12 with serum albumin indicates its feasible transport in the bloodstream for its enhanced anti-cancer properties. Mechanistic studies by western blot analysis demonstrate that benzylic selenocyanates exhibit anti-proliferative activities by modulating key cellular proteins such as Survivin, Bcl-2 and COX-2; this was further supported by molecular docking studies. The results of this study would be helpful in designing suitable chemotherapeutic and chemopreventive drugs in the future.

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.

Tetrazole regioisomers in the development of nitro group-containing antitubercular agents

Tetrazole derivatives containing nitro substituents have been identified as promising antitubercular agents. In this study, the antitubercular potency, selectivity and toxicity of tetrazole 1,5- and 2,5-regioisomers were examined. We prepared a series of 1- and 2-alkyl-5-benzylsulfanyl-2H-tetrazoles and their selenium analogs with various nitro group substitutions. These 1,5- and 2,5-regioisomers were isolated and unambiguously identified using 1H and/or 13C NMR. Among the prepared compounds, 1- and 2-alkyl-5-[(3,5-dinitrobenzyl)sulfanyl]-2H-tetrazole derivatives and their selenium bioisosteres showed the highest antimycobacterial activity, with minimal inhibitory concentration (MIC) values of approximately 1 μM (0.37-0.46 μg mL-1) against Mycobacterium tuberculosis CNCTC My 331/88. The 2-alkyl regioisomers exhibited consistently higher antimycobacterial activity and lower in vitro toxicity against a mammalian cell line compared to the 1-alkyl isomers. The antimycobacterial activity of the 2-alkyl regioisomers was less influenced by the type of alkyl substituent in contrast to 1-alkyl isomers. Furthermore, the 3,5-dinitrobenzyl moiety per se is not the carrier of mutagenicity. These findings encourage further optimization of the 2-alkyl chain to improve the pharmacokinetic properties and toxicity of 2-alkyl-5-[(3,5-dinitrobenzyl)sulfanyl]-2H-tetrazole lead compounds. This journal is

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.