(Phenylthio)acetonitrile

Base Information

• Chemical Name: (Phenylthio)acetonitrile
• CAS No.: 5219-61-4
• Molecular Formula: C8H7NS
• Molecular Weight: 149.216
• Hs Code.: 29309099
• European Community (EC) Number: 226-013-3
• UNII: QYR5862VFA
• DSSTox Substance ID: DTXSID10200216
• Nikkaji Number: J265.540C
• Wikidata: Q83073275
• Mol file: 5219-61-4.mol

Synonyms:(Phenylthio)acetonitrile;5219-61-4;PHENYLTHIOACETONITRILE;2-(Phenylthio)acetonitrile;2-phenylsulfanylacetonitrile;Acetonitrile, (phenylthio)-;Phenylmercaptoacetonitrile;Cyanomethyl phenyl sulfide;2-(phenylsulfanyl)acetonitrile;BRN 2042078;EINECS 226-013-3;QYR5862VFA;4-06-00-01538 (Beilstein Handbook Reference);phenylsulfanyl-acetonitrile;UNII-QYR5862VFA;(Phenylmercapto)acetonitrile;(phenylsulfanyl)acetonitrile;2-phenylsulfanylethanenitrile;SCHEMBL1931888;DTXSID10200216;AMY25703;MFCD00019831;AKOS000216531;CS-0270226;FT-0605013;P1602;EN300-85814;D92138;A828965;Z19751391

Chemical Property of (Phenylthio)acetonitrile

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 0.0101mmHg at 25°C
• Refractive Index: n20/D 1.583(lit.)
• Boiling Point: 146-147 °C14 mm Hg(lit.)
• Flash Point: 146-147°C/14mm
• PSA: 49.09000
• Density: 1.142 g/mL at 25 °C(lit.)
• LogP: 2.30228
• Water Solubility.: Not miscible or difficult to mix in water.
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 149.02992040
• Heavy Atom Count: 10
• Complexity: 129

Purity/Quality:

97% ^*data from raw suppliers

(Phenylthio)acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T
• Statements: 22
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)SCC#N
• Uses: Applications include, electron-deficient aromatics undergo vicarious nucleophilic substitution (VNS) reactions with the anion. Thus the molecule is equivalent to an acetonitrile anion synthon with thiophenate as the leaving group. For example, in the presence of solid NaOH in DMSO, nitrobenzene gives predominantly 4-nitrophenylacetonitrile, along with some of the 2-isomer.

Technology Process of (Phenylthio)acetonitrile

There total 27 articles about (Phenylthio)acetonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

methyl-phenyl-thioether (100-68-5) + cyanomethyl bromide (590-17-0) → (phenylthio)acetonitrile (5219-61-4)

Guidance literature:

In 2,2,2-trifluoroethanol; at 100 ℃; for 24h;

DOI:10.1021/acs.orglett.0c02089

Reference yield: 95.0%

chloroacetonitrile (107-14-2) + thiophenol (108-98-5) → (phenylthio)acetonitrile (5219-61-4)

Guidance literature:

With sodium carbonate; In acetone; at 50 ℃; for 5h;

DOI:10.1021/ja00337a042

Reference yield: 95.0%

sodium thiophenolate (930-69-8) + chloroacetonitrile (107-14-2) → (phenylthio)acetonitrile (5219-61-4)

Guidance literature:

In methanol;

DOI:10.1016/S0040-4039(00)81635-4

upstream raw materials:

sodium thiophenolate

chloroacetonitrile

α-(phenylthio)acetamide

iodoacetonitrile

Downstream raw materials:

2-(phenylsulfonyl)acetonitrile

α-(phenylthio)-pentyl cyanide

2-methyl-2-phenylsulfanylpropanenitrile

2-(phenylthio)butanenitrile

Refernces

Replacing the terminal piperidine in ceritinib with aliphatic amines confers activities against crizotinib-resistant mutants including G1202R

10.1016/j.ejmech.2016.11.046

The research explores the development of new ALK inhibitors to address resistance issues in non-small cell lung cancer (NSCLC) patients. The study focuses on modifying ceritinib by replacing its piperidine fragment with diverse aliphatic amines to improve its efficacy against crizotinib-resistant mutants, particularly the highly resistant G1202R mutant. The researchers synthesized and evaluated a series of compounds, with compound 10 (KRCA-764) showing promising activities against both wild-type ALK and crizotinib-resistant mutants, including G1202R, with an IC50 of 1.8 nM. This compound also exhibited better pharmacokinetic profiles than ceritinib. Key chemicals involved in the synthesis included 4-methyl-2-nitroanisole, phenylthioacetonitrile, sodium hydroxide, Pd/C, and various amines. The study utilized enzymatic and cell-based assays to evaluate the inhibitory activities of the synthesized compounds, and molecular docking studies were performed to understand the binding modes. In vivo xenograft studies in mice demonstrated that compound 10 had similar potency to ceritinib, suggesting further optimization could lead to clinical candidates capable of overcoming ALK mutant resistance.