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
• Article Data: 8

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

General Description

(4-Chlorophenylthio)acetonitrile is a chemical compound with the formula C8H6ClNS. It is a colorless to light yellow liquid with a strong, pungent odor. It is primarily used as an intermediate in the synthesis of other organic compounds, including pharmaceuticals and agrochemicals. It is also used as a reagent for the production of thiazole derivatives, which have various industrial applications. Additionally, it has potential uses in the field of organic synthesis, as it is a versatile building block for the creation of diverse chemical structures. However, (4-Chlorophenylthio)acetonitrile is a hazardous substance and should be handled with care, as it can cause irritation to the eyes, skin, and respiratory system, and may have long-term health effects if not handled properly.

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

Upstream product

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

Downstream Products

• 96514-57-7 α-Formyl-4-chlorphenylmercapto-acetonitril 
• 63923-65-9 Acetic acid (4-chloro-phenylsulfanyl)-cyano-methyl ester 
• 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 
• 1851-09-8 2-(4-chlorobenzenesulfonyl)acetonitrile 
• 110123-87-0 α-chloro-α-p-chlorophenylthioacetonitrile 
• 96514-58-8 α-Acetyl-4-chlorphenylmercapto-acetonitril 

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.

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.

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.