18527-19-0

Basic information

• Product Name: (4-CHLOROPHENYLTHIO)ACETONITRILE
• Synonyms: 2-(4-CHLOROPHENYLTHIO)ETHANENITRILE;2-[(4-CHLOROPHENYL)THIO]ACETONITRILE;(4-CHLOROPHENYLTHIO)ACETONITRILE;BUTTPARK 76\07-78;P-CHLOROPHENYLTHIOACETONITRILE;[(4-Chlorophenyl)sulphanyl]acetonitrile;2-(4-chlorophenyl)sulfanylethanenitrile
• CAS NO: 18527-19-0
• Molecular Formula: C₈H₆ClNS
• Molecular Weight: 183.66
• Mol File: 18527-19-0.mol

Chemical Properties

• Melting Point: 79 °C
• Boiling Point: 299.7°Cat760mmHg
• Flash Point: 135.1°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 0.00117mmHg at 25°C
• Refractive Index: 1.603
• CAS DataBase Reference: (4-CHLOROPHENYLTHIO)ACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (4-CHLOROPHENYLTHIO)ACETONITRILE(18527-19-0)
• EPA Substance Registry System: (4-CHLOROPHENYLTHIO)ACETONITRILE(18527-19-0)

Safety Data

• Statements: 20/21/22
• Safety Statements: 26-36/37/39
• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 18527-19-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(4-Chlorophenylthio)acetonitrile is used as a chemical intermediate for the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its ability to form diverse chemical structures makes it a valuable component in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, (4-Chlorophenylthio)acetonitrile serves as an intermediate in the production of various agrochemicals, such as pesticides and herbicides, to help protect crops and enhance agricultural productivity.
Used in Organic Synthesis:
(4-Chlorophenylthio)acetonitrile is used as a versatile building block in organic synthesis, enabling the creation of a wide array of chemical structures for various applications across different industries.
Used in Thiazole Derivatives Production:
(4-Chlorophenylthio)acetonitrile is used as a reagent in the production of thiazole derivatives, which have diverse industrial applications, including in the development of dyes, pigments, and other specialty chemicals.
Safety Precautions:
Due to its hazardous nature, (4-Chlorophenylthio)acetonitrile should be handled with care to minimize the risk of irritation to the eyes, skin, and respiratory system. Proper safety measures, including the use of personal protective equipment and adherence to safety guidelines, are essential to prevent potential long-term health effects.

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

Upstream product

• 106-54-7 p-Chlorothiophenol 
• 75-05-8 acetonitrile 
• 123-09-1 4-chlorophenyl methyl sulfide 
• 6011-14-9 2-aminoacetonitrile hydrochloride 
• 53830-54-9 4-chlorophenyl benzyl sulfide 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 107-14-2 chloroacetonitrile 
• 18803-44-6 sodium p-chlorothiophenolate 
• 590-17-0 cyanomethyl bromide 

Downstream Products

• 50837-18-8 2-(4-bromophenylthio)acetamidoxime 
• 18518-83-7 2-(p-chlorophenylthio)-2-methyl-propionitrile 
• 124405-80-7 5-(4-Chloro-phenylsulfanyl)-N'-phenyl-pyrimidine-2,4,6-triamine 
• 104856-95-3 3-<<(4-chlorophenyl)thio>methyl>-5-<(phenylmethyl)thio>pyrimido<5,4-e>-1,2,4-triazin-7-amine 
• 104856-97-5 3-<<(4-chlorophenyl)sulfinyl>methyl>pyrimido<5,4-e>-1,2,4-triazine-5,7-diamine 
• 104856-96-4 3-<<(4-chlorophenyl)thio>methyl>pyrimido<5,4-e>-1,2,4-triazine-5,7-diamine 
• 112181-66-5 3-(4-Chloro-phenylsulfanyl)-7,8-dimethoxy-2-(4-methyl-piperazin-1-yl)-benzo[b][1,8]naphthyridine 
• 112181-65-4 3-(4-Chloro-phenylsulfanyl)-7,8-dimethoxy-2-morpholin-4-yl-benzo[b][1,8]naphthyridine 
• 112181-60-9 3-(4-Chloro-phenylsulfanyl)-2-(4-methyl-piperazin-1-yl)-benzo[b][1,8]naphthyridine 
• 112181-59-6 3-(4-Chloro-phenylsulfanyl)-2-morpholin-4-yl-benzo[b][1,8]naphthyridine 
• 112181-58-5 3-(4-Chloro-phenylsulfanyl)-2-piperidin-1-yl-benzo[b][1,8]naphthyridine 
• 63923-65-9 Acetic acid (4-chloro-phenylsulfanyl)-cyano-methyl ester 
• 1851-09-8 2-(4-chlorobenzenesulfonyl)acetonitrile 
• 110123-87-0 α-chloro-α-p-chlorophenylthioacetonitrile 

Relevant articles and documents

Dealkylative intercepted rearrangement reactions of sulfur ylides

Sulfur ylides are well-known to undergo sigmatropic rearrangement reaction. Herein, we describe a novel reactivity of sulfur ylides, which provides access to the product of a formal functional group metathesis upon dealkylative interception of the rearrangement process. Using a simple iron catalyst and in situ generated diazoalkanes this method provides access to α-mercaptoacetonitrile derivatives.

Iron-catalysed carbene-transfer reactions of diazo acetonitrile

A continuous-flow protocol for the synthesis of diazo acetonitrile was developed. It was further applied in iron-catalysed insertion reactions of diazo acetonitrile into N-H and S-H bonds to yield valuable α-substituted acetonitrile, including gram-scale synthesis.

Inhibitors of the Diadenosine Tetraphosphate Phosphorylase Rv2613c of Mycobacterium tuberculosis

The intracellular concentration of diadenosine tetraphospate (Ap4A) increases upon exposure to stress conditions. Despite being discovered over 50 years ago, the cellular functions of Ap4A are still enigmatic. If and how the varied Ap4A is a signal and involved in the signaling pathways leading to an appropriate cellular response remain to be discovered. Because the turnover of Ap4A by Ap4A cleaving enzymes is rapid, small molecule inhibitors for these enzymes would provide tools for the more detailed study of the role of Ap4A. Here, we describe the development of a high-throughput screening assay based on a fluorogenic Ap4A substrate for the identification and optimization of small molecule inhibitors for Ap4A cleaving enzymes. As proof-of-concept we screened a library of over 42, 000 compounds toward their inhibitory activity against the Ap4A phosphorylase (Rv2613c) of Mycobacterium tuberculosis (Mtb). A sulfanylacrylonitril derivative with an IC50 of 260 ± 50 nM in vitro was identified. Multiple derivatives were synthesized to further optimize their properties with respect to their in vitro IC50 values and their cytotoxicity against human cells (HeLa). In addition, we selected two hits to study their antimycobacterial activity against virulent Mtb to show that they might be candidates for further development of antimycobacterial agents against multidrug-resistant Mtb.

Cs2CO3-promoted carbon–sulfur bond construction via cross dehydrogenative coupling of thiophenols with acetonitrile

A novel protocol for the construction of carbon–sulfur bonds has been achieved via halogen-free Cs2CO3-promoted cross dehydrogenative coupling (CDC) of thiophenols with acetonitrile. This transformation provides a straightforward route to the synthesis of sulfenylated acetonitriles in up to 80% yield.

Synthesis of organic sulfides via Zn/AlCl3 system in aqueous media

An efficient procedure for preparation of various sulfides has been introduced through a simple reaction of disulfides with suitable alkyl or aryl halides which is promoted by commercial zinc powder in the presence of AlCl3 in aqueous media at 65°C.

Intramolecular Stereospecific Pummerer Reactions of Aryl (Substituted-methyl) Sulfoxides Bearing Electron-withdrawing Groups with Acetic Anhydride

The Pummerer reaction of optically active cyanomethyl aryl sulfoxides with acetic anhydride gave the corresponding α-acetoxy sulfides which were induced with a partial asymmetry nearly 30percent at α-carbon, while the 18O-label of the original sulfoxides was retained in more than 85percent in the resulting ester, the Pummerer reaction product.Kinetic experiments with cyanomethyl (p-substituted phenyl) sulfoxides and α,α-dideuterated cyanomethyl p-tolyl sulfoxide in the reaction with acetic anhydride containing a small amount of acetic acid revealed that the rates were correlated with Hammett ?-values and ρ-value of -0.70 was obtained, while the kinetic isotope effect was practically nil, i.e., kH/kD=1.01.These observations indicate clearly that the rearrangement is intramolecular and proceeds via forming a very intimate ion-pair and the rate-determining step is believed to be the S-O bond cleavage after the initial reversible acylation and deprotonation.Elimination of acetic acid proceeds through the Eleb type process.The uneven distribution of 18O in the two oxygens of the resulted ester, i.e., ether and carbonyl oxygens, suggests the recombination of the α-sulfenyl carbonium ion and acetate ion to be very rapid.The pummerer reaction of optically active N,N-dimethyl-p-tolyl-sulfinylacetamide with excess acetic anhydride also gave the corresponding α-acetoxy sulfide in optically active form.In the presence of di-cyclohexylcarbodiimide (DCC), the Pummerer reaction was found to be highly stereoselective affording the corresponding α-acetoxy sulfide with 65percent e.e.Other optically active α-carbonyl-substituted alkyl sulfoxides, i.e., ethyl p-tolylsulfinylacetate and ω-(p-tolylsulfinyl)acetophenone also gave the corresponding highly optically active Pummerer rearrangement products in the treatment with acetic anhydride/DCC system.The Pummerer reaction of the 18O-labeled sulfoxides with acetic anhydride/DCC system gave the corresponding α-acetoxy sulfides which retained much of the original 18O-labels of the sulfoxides.These observations reveal clearly that in the Pummerer reaction of these compounds the acetoxyl migration is intramolecular and takes place through intimate ion-pairs.

Composition and process for promoting the growth of crop plants

Compounds of the formula wherein Ar is (substituted) phenyl or naphthyl, X is oxygen, sulfur, SO or SO2, n is 1-3 and R is CN or C(NH2)NOR1, (wherein R1 is preferably hydrogen) are useful as safeners in crop protection.