2082-66-8

Basic information

• Product Name: 2-CHLOROBENZYL THIOCYANATE
• Synonyms: 2-CHLOROBENZYL THIOCYANATE
• CAS NO: 2082-66-8
• Molecular Formula: C₈H₆ClNS
• Molecular Weight: 183.65794
• Mol File: 2082-66-8.mol

Chemical Properties

• Boiling Point: 140°C/5mmHg(lit.)
• Flash Point: 130°C
• Appearance: /
• Density: 1.297g/cm³
• Vapor Pressure: 0.00196mmHg at 25°C
• Refractive Index: 1.5880 to 1.5920
• CAS DataBase Reference: 2-CHLOROBENZYL THIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROBENZYL THIOCYANATE(2082-66-8)
• EPA Substance Registry System: 2-CHLOROBENZYL THIOCYANATE(2082-66-8)

Safety Data

• HazardClass: IRRITANT-HARMFUL
• Hazardous Substances Data: 2082-66-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chlorobenzyl thiocyanate is used as a reagent for the preparation of pharmaceutical compounds, leveraging its properties to contribute to the synthesis of various medicinal agents. Its versatility in organic synthesis allows it to be a key component in creating a range of therapeutically relevant molecules.
Used in Organic Synthesis:
In the realm of organic synthesis, 2-chlorobenzyl thiocyanate is utilized as a building block for the creation of different functionalized thiocyanates and related compounds. This application underscores its importance in the development of novel chemical entities with potential applications in various fields.
Used in Chemical Reactions:
2-Chlorobenzyl thiocyanate is known for its potential use in a variety of chemical reactions, where it can act as an intermediate or a reactant to facilitate the formation of desired products. Its participation in these reactions is crucial for advancing the synthesis of new compounds with specific properties and applications.

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

Upstream product

• 333-20-0 potassium thioacyanate 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 163276-49-1 1-thiocyanatopyrrolidine-2,5-dione 
• 1147550-11-5 ammonium thiocyanate 
• 512180-26-6 2-(2-chlorobenzyloxy)tetrahydro-2H-pyran 
• 39718-00-8 2-chlorobenzylthiol 
• 95-49-8 2-methylchlorobenzene 

Downstream Products

• 5518-09-2 2-(naphthalen-1-yl)malononitrile 
• 25230-06-2 3-Pyridylmalononitrile 
• 86239-14-7 (4-Bromophenyl)malononitrile 
• 98321-21-2 2-(4-Dicyanomethyl-2,3,5,6-tetramethyl-phenyl)-malononitrile 
• 140863-12-3 1-cyanomethyl-4-di(cyanomethyl)tetrachlorobenzene 
• 32122-65-9 (2-Chlorophenyl)malononitrile 
• 6251-01-0 9,9,10,10-tetracyano-2,6-naphthoquinodimethane 
• 18389-97-4 11,11,12,12-tetracyano-1,4-naphthoquinodimethan 
• 56403-70-4 2,5-Dibromo-7,7,8,8-tetracyano-p-quinodimethane 
• 21003-99-6 2,5-dimethoxy-7,7,8,8-tetracyano-p-quinodimethane 
• 96802-43-6 2-(4-Dicyanomethyl-2,5-dimethoxy-phenyl)-malononitrile 
• 124345-65-9 2-(2,5-Dibromo-4-dicyanomethyl-phenyl)-malononitrile 
• 3041-40-5 2-phenylmalononitrile 
• 33534-87-1 α-(p-Methoxyphenyl)-malononitrile 

Relevant articles and documents

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.

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.

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.

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.

Synthesis of alkyl thiocyanates from alcohols using a polymer-supported thiocyanate ion promoted by cyanuric chloride/dimethylformamide

A convenient procedure for one-pot conversion of alcohols into the corresponding alkyl thiocyanates in the presence of cross-linked poly (N-propyl-4-vinylpyridinium) thiocyanate ion [P4-VP]Pr-SCN, promoted by cyanuric chloride/dimethylformamide, is described. Various alcohols were converted to their corresponding alkyl thiocyanates and it was observed that substituted benzyl alcohol with electron-withdrawing or electron-donating groups were transformed into the corresponding benzyl thiocyanate derivatives in high to excellent yields in a short reaction time but, sterically hindered alcohols produced the corresponding thiocyanates in very low yields.

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.

Nanomagnetic double-charged diazoniabicyclo[2.2.2]octane dichloride silica as a novel nanomagnetic phase-transfer catalyst for the aqueous synthesis of benzyl acetates and thiocyanates

Abstract Nanomagnetic double-charged diazoniabicyclo[2.2.2]octane dichloride silica hybrid (Fe3O4@SiO2/DABCO) was used as an efficient and magnetically recoverable phase-transfer catalyst (PTC) for nucleophilic substitution reactions of benzyl halides for the synthesis of benzyl acetates and thiocyanates in good to excellent yields at 100 C in water. No evidence for the formation of by-products, for example, isothiocyanate or benzyl alcohol was observed and the products were obtained in pure form without further purification. The catalyst was easily separated with the assistance of an external magnetic field from the reaction mixture and reused for several consecutive runs without significant loss of its catalytic efficiency.

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.

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.