3012-37-1

Basic information

• Product Name: Benzyl thiocyanate
• Synonyms: alpha-Thiocyanatotoluene;Benzylthiocyanide;Solvat 14;solvat14;Thiocyanic acid, phenylmethyl ester;Thiocyanicacid,phenylmethylester;Toluene, alpha-thiocyanato-;Tropeolin
• CAS NO: 3012-37-1
• Molecular Formula: C₈H₇NS
• Molecular Weight: 149.21
• EINECS: 221-144-2
• Mol File: 3012-37-1.mol

Chemical Properties

• Melting Point: 39-41 °C(lit.)
• Boiling Point: 230-235 °C(lit.)
• Flash Point: >230 °F
• Appearance: Almost white to yellow crystals or cryst. powder
• Density: 1.32
• Vapor Pressure: 0.0151mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: 2-8°C
• Solubility: diethyl ether: soluble0.5g/10 mL, clear to very faintly turbid,
• Water Solubility: insoluble
• Sensitive: Moisture Sensitive
• BRN: 1859726
• CAS DataBase Reference: Benzyl thiocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl thiocyanate(3012-37-1)
• EPA Substance Registry System: Benzyl thiocyanate(3012-37-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-32
• Safety Statements: 13-36/37-50A
• RIDADR: UN 1759 8/PG 2
• WGK Germany: 3
• RTECS: XK8155000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 3012-37-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzyl thiocyanate is used as a stimulant for chlortetracycline biosynthesis during industrial fermentations, enhancing the production of this important antibiotic.
Used in Research:
Benzyl thiocyanate is used in research studies to investigate the effects of various dietary compounds on the α-hydroxylation of N-nitrosopyrrolidine in male F344 rats in vitro, contributing to the understanding of the compound's potential impact on health.
Used in Cancer Prevention:
Benzyl thiocyanate has been found to inhibit methylazoxymethanol acetate-induced intestinal carcinogenesis in rats, suggesting its potential use as a cancer-preventive agent.
Used in Genotoxicity Studies:
Benzyl thiocyanate is utilized to study its effects on unscheduled DNA synthesis for some genotoxic carcinogens in rats, providing insights into its role in mitigating the harmful effects of certain carcinogens.
Used in Biotransformation:
Benzyl thiocyanate undergoes biotransformation into dibenzyl disulfide by Streptomyces aureofaciens, a process that may have applications in the production of valuable chemical compounds or in bioremediation efforts.

Synthesis Reference(s)

Synthesis, p. 184, 1977Tetrahedron Letters, 18, p. 4417, 1977 DOI: 10.1016/S0040-4039(01)83524-3

Hazard

Strong irritant to skin, tissue. Moderate fire hazard.

Safety Profile

Poison by subcutaneous andintraperitoneal routes. Whenheated to decomposition it emits very toxic fumes ofNOx, SOx, and CN??.

Purification Methods

Crystallise the thiocyanate from EtOH or aqueous EtOH. [Beilstein 6 H 460, 6 IV 2680.]

InChI:InChI=1/C8H7NS/c9-7-10-6-8-4-2-1-3-5-8/h1-5H,6H2

Upstream product

• 333-20-0 potassium thioacyanate 
• 100-44-7 benzyl chloride 
• 463-58-1 carbon oxide sulfide 
• 28269-82-1 phenyl S-benzylisothiocarbamide 
• 14642-79-6 benzyloxy-trimethylsilane 
• 1147550-11-5 ammonium thiocyanate 
• 53172-91-1 (benzyloxy)(tert-butyl)dimethylsilane 
• 113848-68-3 C₂₄H₂₁N₂S⁽¹⁺⁾*CNS^(1-) 
• 83319-08-8 C₂₅H₂₂NS⁽¹⁺⁾*CNS^(1-) 
• 130594-28-4 C₈H₉NSSe 
• 100-39-0 benzyl bromide 
• 2911-22-0 6-methyl-4-oxo-2-thioxo-3,4-dihydro-2H-1,3-oxazine 
• 74119-86-1 1,1,2,2,3,3-Hexaethylguanidiniumthiocyanat 
• 540-72-7 sodium thiocyanide 

Downstream Products

• 117864-88-7 S-benzyl-1,1-dimethyl-iso thiosemicarbazide 
• 42049-11-6 Methylen-N,N'-bis-(S-benzyl-thiocarbamat) 
• 23547-13-9 N-<2-Chlor-cyclohexyl>-thiolkohlensaeureamid-S-benzylester 
• 5316-72-3 2-(benzylthio)-4-methylthiazole 
• 76684-17-8 Benzyl(1-chlor-1,2,2,2-tetrafluorethyl)sulfid 
• 111860-65-2 benzyl-trifluorovinyl sulfide 
• 4403-73-0 benzylsulfinic acid 
• 506-77-4 cyanogen chloride 
• 1939-99-7 benzenesulfonyl chloride 
• 100-44-7 benzyl chloride 
• 177703-80-9 2-phenylmethanesulfonylacetonitrile 
• 119-61-9 benzophenone 
• 100-53-8 phenylmethanethiol 
• 100-52-7 benzaldehyde 

Relevant articles and documents

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.

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.

Thiocyanation and 2-Amino-1,3-thiazole Formation in Water Using Recoverable and Reusable Glycosylated Resorcin[4]arene Cavitands

A family of three spatially directional resorcin[4]arene cavitand glycoconjugates (RCGs) have been applied as efficient recoverable and reusable inverse phase transfer catalysts for eco- A nd environmentally friendly thiocyanation and 2-amino-1,3-thiazole formation reactions in water. The results show that RCGs (1 mol %) were capable of hosting and catalyzing various water-insoluble bromo/thiocyanato substrates in water without the use of any co-organic solvents. The recoverability and reusability of RCG catalytic systems, that is, RCG1 and RCG3, were also examined upon a simple extraction of the desired products using DCM or ethyl acetate, followed by subjecting the recovered aqueous solution containing the RCG catalysts to the next reaction cycles.

A rings-in-pores net: Crown ether-based covalent organic frameworks for phase-transfer catalysis

We herein present a new family of crown ether-based covalent organic frameworks (CE-COFs) for the first time. The CE-COFs show excellent phase-transfer catalytic performance in various nucleophilic substitution reactions.

Selectfluor-initiated cyanation of disulfides to thiocyanates

A Selectfluor-initiated cyanation of disulfides to thiocyanates has been developed. In this process, Selectfluor was employed as the oxidant and trimethylsilyl cyanide was used as the cyanation reagent. It provides an eco-friendly and simple way to synthesize the thiocyanates.

Fluorium-Initiated Dealkylative Cyanation of Thioethers to Thiocyanates

Thioethers are converted to thiocyanates via fluorium-initiated dealkylative cyanation. Selectfluor is used as the oxidant, and trimethylsilyl cyanide is used as the cyanation reagent. The well-streamlined procedure is user-friendly, operationally simple, and step-economical. The current mechanistic studies show that the sulfur radical cation and cyano radical are both involved. They combine to deliver cyanosulfonium, an intermediate toward thiocyanate after dealkylation. Alternatively, a nucleophilic mechanism is also possible. Our dealkyaltive cyanation is also efficient in synthesizing thiocyanates with strongly electrophilic functionalities.

Electrochemical ipso-Thiocyanation of Arylboron Compounds

An operationally simple electrochemical method for the transition-metal-free ipso-thiocyanation of arylboronic acids and aryl trifluoroborates has been developed. The SCN electrophile is generated in situ by anodic oxidation of thiocyanate anions, which avoids formation of salt waste and prevents unwanted side reactions arising from chemical oxidants. The reaction proceeds regiospecifically, and the scope extends to non-activated aromatic systems. (Figure presented.).

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.

Crown ether functionalized magnetic hydroxyapatite as eco-friendly microvessel inorganic-organic hybrid nanocatalyst in nucleophilic substitution reactions: an approach to benzyl thiocyanate, cyanide, azide and acetate derivatives

In this paper, high catalytic activity of 4′,4″-diformyl dibenzo-18-crown-6 anchored onto the functionalized magnetite hydroxyapatite (γ-Fe2O3@HAp–Crown) as a new, versatile and magnetically recoverable catalyst, was prepared. It evaluated as phase-transfer catalyst and molecular host system for nucleophilic substitution reactions of benzyl halides with thiocyanate, cyanide, azide and acetate anions in water. No evidence for the formation of by-products was observed and the products obtained in pure form without further purification. The nanocomposite was easily removed from solution via application of a magnetic field, allowing straightforward recovery and reuse. The synthesized nanocomposite was characterized by several techniques such as FT-IR, TGA-DTG, EDX, XRD, BET, FE-SEM, TEM and VSM.