306278-24-0

Basic information

• Product Name: 4-chlorophenyl 2-phenylimidazo[1,2-a]pyridin-3-yl sulfide
• Synonyms: 4-chlorophenyl 2-phenylimidazo[1,2-a]pyridin-3-yl sulfide
• CAS NO: 306278-24-0
• Molecular Formula: C₁₉H₁₃ClN₂S
• Molecular Weight: 336.83792
• Mol File: 306278-24-0.mol
• Article Data: 26

Chemical Properties

• Appearance: /
• Density: 1.27±0.1 g/cm3(Predicted)
• PKA: 4.49±0.50(Predicted)
• CAS DataBase Reference: 4-chlorophenyl 2-phenylimidazo[1,2-a]pyridin-3-yl sulfide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chlorophenyl 2-phenylimidazo[1,2-a]pyridin-3-yl sulfide(306278-24-0)
• EPA Substance Registry System: 4-chlorophenyl 2-phenylimidazo[1,2-a]pyridin-3-yl sulfide(306278-24-0)

Safety Data

• Hazardous Substances Data: 306278-24-0(Hazardous Substances Data)

Upstream product

• 106-54-7 p-Chlorothiophenol 
• 4105-21-9 2-phenylimidazo[1,2-a]pyridine 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 504-29-0 2-aminopyridine 
• 98-86-2 acetophenone 
• 2751-25-9 p-chlorophenylsulfonyl hydrazide 
• 7205-80-3 1-(ethylsulfonyl)-4-chlorobenzene 
• 1146-44-7 4,4'-dichlorophenyl thiosulfonate 
• 100-03-8 4-chlorobenzenesulfinic acid 
• 1213-40-7 S-(4-chlorophenyl)benzene thiosulfonate 
• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 70-11-1 α-bromoacetophenone 
• 1679-18-1 4-Chlorophenylboronic acid 

Relevant articles and documents

Design, synthesis and anticancer activity of sulfenylated imidazo-fused heterocycles

We report herein, the design, synthesis and study of anticancer properties of sulfenylated 2-phenylimidazo[1,2-a]pyridines and their analogues. A set of twenty sulfenylated imidazo[1, 2-a]pyridine derivatives were synthesized. Whereby elusive amendments to the imidazo[1,2-a]pyridine motif confer dramatic changes in functional affinity of a novel action to modulate anticancer activity in seven different human cancer cell lines i.e.: MDA MB 231 (breast), HepG2 (liver), Hela (cervical), A549 (lung), U87MG (glioblastoma), SKMEL-28 (skin melanoma) and DU-145 (prostate) by employing MTT assay. Among the series, compounds 4e (naphthalene), 4f (styrene) and 4h (thiomethyl) showed potent activity towards human liver cancer cells HepG2. Cell cycle analysis results revealed that these compounds arrested the cell cycle at G2/M phase and induced apoptosis in human liver cancer cells HepG2. It was further confirmed by Hoechst staining, Measurement of mitochondrial membrane potential (ΔΨm) and Annexin V-FITC assay.

Unconventional Reactivity with DABCO-Bis(sulfur dioxide): C–H Bond Sulfenylation of Imidazopyridines

This work highlights the unexpected and unprecedented outcome of the reactivity with DABCO-bis(sulfur dioxide). The use of this reagent led to the exclusive introduction of a sulfur atom on the C-3 position of imidazopyridines instead of a sulfone group.

S-Aryl Arenesulfonothioate and Copper Acetate Mediated Arylthiolation of 2-Arylpyridines and Heteroarenes

Copper acetate mediated regioselective ortho-arylthiolation of 2-arylpyridines has been accomplished for the first time using S-aryl arenesulfonothioate as the arylthiolating agent. The reaction shows good functional group tolerance and gives thioarylated products in 67-89% yields. This reagent is a good alternative to unpleasant smelling arylthiols. Experimental evidence suggests an unprecedented insertion of an arylthio unit from both parts of the reagent (SPh and p-TolSO2) in the presence of copper acetate. Indoles and imidazopyridines also undergo facile reaction at the C-3 position and furnish thioarylated derivatives in good yields.