2392-68-9

Basic information

• Product Name: 3-CHLOROPHENYL ISOTHIOCYANATE
• Synonyms: 3-Chlorophenylisothiocyanate,98%;3-Chlorophenyl isothiocyanate 98%;1-Chloro-3-isothiocyanatobenzene;Benzene, 1-chloro-3-isothiocyanato-;Isothiocyanic acid, 3-chlorophenyl ester;Isothiocyanic acid, m-chlorophenyl ester;isothiocyanicacid,3-chlorophenylester;isothiocyanicacid,m-chlorophenylester
• CAS NO: 2392-68-9
• Molecular Formula: C₇H₄ClNS
• Molecular Weight: 169.63
• EINECS: -0
• Product Categories: Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;Organic Building Blocks;Sulfur Compounds;Thiocyanates/Isothiocyanates
• Mol File: 2392-68-9.mol

Chemical Properties

• Boiling Point: 249-250 °C
• Flash Point: >110°C
• Appearance: clear yellow liquid
• Density: 1.292
• Vapor Pressure: 0.0361mmHg at 25°C
• Refractive Index: 1.658-1.66
• Water Solubility: 33.93mg/L(25 oC)
• Sensitive: Moisture Sensitive
• BRN: 636856
• CAS DataBase Reference: 3-CHLOROPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLOROPHENYL ISOTHIOCYANATE(2392-68-9)
• EPA Substance Registry System: 3-CHLOROPHENYL ISOTHIOCYANATE(2392-68-9)

Safety Data

• Hazard Codes: T,Xn
• Statements: 42-36/37/38-23/24/25-20/21/22
• Safety Statements: 45-36/37/39-26-37/39
• RIDADR: 2810
• WGK Germany: 3
• RTECS: NX8474500
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 2392-68-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Chlorophenyl isothiocyanate is used as a synthetic intermediate for the creation of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
As a reactive compound, 3-chlorophenyl isothiocyanate is also utilized in chemical research to explore its properties and potential reactions with other molecules. This can lead to the discovery of new chemical entities and advancements in the field of chemistry.
Used in the Synthesis of Specific Compounds:
3-Chlorophenyl isothiocyanate has been specifically used in the synthesis of complex organic molecules such as 2-[(3-chlorophenyl)amino]naphtho[2,1-b]furo-5H-[3,2-d][1,3,4]thiadiazolo[3,2-i]pyrimidin-5-one and (S)-N-[3-N-(3-chlorophenyl)-4-(3-fluorophenyl)piperazine]-1-carbothioamido-2-oxooxazolidin-5-yl)methyl]acetamide. These compounds may have potential applications in various fields, including pharmaceuticals and materials science.

InChI:InChI=1/C7H4ClNS/c8-6-2-1-3-7(4-6)9-5-10/h1-4H

Upstream product

• 1219-84-7 1,3-bis(3-chlorophenyl)thiourea 
• 103-72-0 phenyl isothiocyanate 
• 108-42-9 3-chloro-aniline 
• 463-71-8 thiophosgene 
• 86317-29-5 O-(4-methoxyphenyl) N-3-chlorophenylthioncarbamate 
• 75-15-0 carbon disulfide 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 1414781-37-5 C₇H₆ClNS₂*C₆H₁₂N₂ 
• 53662-48-9 m-chlorophenyldithiocarbamic acid triethylamine salt 
• 1125527-00-5 C₂₀H₁₆Cl₂N₄S₂ 
• 454426-44-9 N-(2,4-dibromo-phenyl)-N'-phenyl-thiourea 
• 19172-47-5 Lawessons reagent 
• 2909-38-8 m-chlorophenyl isocyanate 

Downstream Products

• 114765-14-9 azetidine-1-carbothioic acid 3-chloro-anilide 
• 109100-41-6 N-(3-chlorophenyl)piperidine-1-carbothioamide 
• 108650-74-4 4-methyl-piperazine-1-carbothioic acid-(3-chloro-anilide) 
• 4251-08-5 1-phenyl-3-m-chlorophenyl thiocarbamide 
• 1219-84-7 1,3-bis(3-chlorophenyl)thiourea 
• 22007-42-7 (3-chloro-phenyl)-thiocarbamic acid O-ethyl ester 
• 857592-69-9 S-ethyl-N-(3-chloro-phenylthiocarbamoyl)-N'-isopropyl-isothiourea 
• 873968-04-8 phenyl-thiopropiolic acid-(3-chloro-anilide) 
• 119379-82-7 1,4-bis-(3-chloro-phenyl)-thiosemicarbazide 
• 4947-89-1 1-(3-chlorophenyl)-2-thiourea 
• 42135-76-2 4-(3-chlorophenyl)-3-thiosemicarbazide 
• 93535-53-6 hydrazine-N,N'-bis-carbothioic acid bis-(3-chloro-anilide) 
• 90002-09-8 (3-chloro-phenyl)-[1,2,3]thiadiazol-5-yl-amine 
• 3100-75-2 1-(3-chloro-phenyl)-3-(4-p-tolyl-thiazol-2-yl)-thiourea 

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Design, computational studies, synthesis and biological evaluation of thiazole-based molecules as anticancer agents

Background: Abolition of cancer warrants effective treatment modalities directed towards specific pathways dysregulated in tumor proliferation and survival. The antiapoptotic Bcl-2 proteins are significantly altered in several tumor types which position them as striking targets for therapeutic intervention. Here we designed, computationally evaluated, synthesized, and biologically tested structurally optimized thiazole-based small molecules as anticancer agents. Methods: The virtually designed 200 molecules were subjected to rigorous docking and in silico ADME-Toxicity studies. Out of this, 23 skeletally diverse thiazole-based molecules which passed pan assay interference compounds (PAINS) filter and were synthetically feasible were synthesized in 3 steps using cheap and readily available reagents. The molecules were in vitro evaluated against Bcl-2-Jurkat, A-431 cancerous cell lines and ARPE-19 cell lines. Molecular Dynamics (MD) simulation studies were performed to analyse conformational changes induced by ligand 32 in Bcl-2. Flow cytometry analysis of compound 32 treated Bcl-2 cells was done to check apoptosis. Results: The molecules exhibited appreciable interactions with Bcl-2 and were having acceptable drug like properties as tested in silico. The multi step synthesis yielded 23 skeletally diverse thiazole-based molecules in up to 80% yield. The molecules simultaneously inhibited Bcl-2 Jurkat cells in vitro without causing detectable toxicity to normal cells (ARPE-19 cells). Among them molecules 32, 50, 53, 57 and 59 showed considerable activities against Bcl-2 Jurkat and A-431cell lines at concentrations ranging from 32–46 μM and 34–52 μM, respectively. The standard doxorubicin exhibited IC50 in Bcl-2 Jurkat and A-431cell lines at 45.87 μM and 42.37 μM, respectively. The molecule 32, almost equipotent in both the cell lines was subjected to molecular dynamics (MD) simulation with Bcl-2 protein (4IEH). It was shown that 32 interacted with protein majorly via hydrophobic interactions and few H-bonding interactions. Fluorescence-activated cell sorting (FACS) analysis established that molecule is dragging cancerous cells towards apoptosis. Discussion and conclusion: The chemical intuition was checked by computation coupled with biological results confirmed that thiazole-based hits have the potential to be developed downstream into potent and safer leads against antiapoptotic Bcl-2 cells.