24068-15-3

Basic information

• Product Name: 2-(CHLOROMETHYL)-5-(4-CHLOROPHENYL)-1,3,4-OXADIAZOLE
• Synonyms: ASISCHEM D38790;2-CHLOROMETHYL-5-(4-CHLOROPHENYL)-1,2,4-OXADIAZOLE;2-(CHLOROMETHYL)-5-(4-CHLOROPHENYL)-1,3,4-OXADIAZOLE;AKOS BBS-00006671;TIMTEC-BB SBB005577;2-CHLOROMETHYL-5-(4-CHLOROPHENYL)-1,2,4- OXADIAZOLE 98%;2-Chloromethyl-5-(4-chlorophenyl)-1,3,4-oxadiazole,98%
• CAS NO: 24068-15-3
• Molecular Formula: C₉H₆Cl₂N₂O
• Molecular Weight: 229.06
• Mol File: 24068-15-3.mol
• Article Data: 25

Chemical Properties

• Melting Point: 81-85 °C
• Boiling Point: 343.8°Cat760mmHg
• Flash Point: 161.7°C
• Appearance: /
• Density: 1.4813 (rough estimate)
• Vapor Pressure: 0.000136mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• CAS DataBase Reference: 2-(CHLOROMETHYL)-5-(4-CHLOROPHENYL)-1,3,4-OXADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(CHLOROMETHYL)-5-(4-CHLOROPHENYL)-1,3,4-OXADIAZOLE(24068-15-3)
• EPA Substance Registry System: 2-(CHLOROMETHYL)-5-(4-CHLOROPHENYL)-1,3,4-OXADIAZOLE(24068-15-3)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-25
• Safety Statements: 37/39-26-45
• HazardClass: IRRITANT
• Hazardous Substances Data: 24068-15-3(Hazardous Substances Data)

Usage

Chemical Properties

light yellow crystalline needles

InChI:InChI=1/C9H6Cl2N2O/c10-5-8-12-13-9(14-8)6-1-3-7(11)4-2-6/h1-4H,5H2

Upstream product

• 50677-27-5 1-(chloroacetyl)-2-(4-chlorobenzoyl)hydrazine 
• 536-40-3 4-chlorobenzoic acid hydrazide 
• 74974-54-2 2-chloro-1,1,1-trimethoxyethane 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 74-11-3 para-chlorobenzoic acid 
• 79-11-8 chloroacetic acid 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 79-04-9 chloroacetyl chloride 
• 62911-97-1 1-(4-chloro-benzoyloxy)-1H-benzotriazole 

Downstream Products

• 50677-45-7 3-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-3H-thiazol-2-ylideneamine 
• 50677-44-6 1-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-1H-pyridin-2-ylideneamine 
• 125231-80-3 o-Tolyl-dithiocarbamic acid 5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-ylmethyl ester 
• 125231-81-4 p-Tolyl-dithiocarbamic acid 5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-ylmethyl ester 
• 125231-79-0 (4-Chloro-phenyl)-dithiocarbamic acid 5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-ylmethyl ester 
• 125231-78-9 Phenyl-dithiocarbamic acid 5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-ylmethyl ester 
• 125231-84-7 2-(4-Chloro-phenyl)-5-phenyl-[1,3,4]oxadiazolo[3,2-d][1,3,4]thiadiazine-6-thione 
• 125231-90-5 [2-(4-Chloro-phenyl)-[1,3,4]oxadiazolo[3,2-b][1,5,2]dithiazin-(6E)-ylidene]-phenyl-amine 
• 125231-96-1 2-(4-Chloro-phenyl)-5-p-tolyl-[1,3,4]oxadiazolo[3,2-d][1,3,4]thiadiazin-6-one 
• 125231-87-0 2-(4-Chloro-phenyl)-5-p-tolyl-[1,3,4]oxadiazolo[3,2-d][1,3,4]thiadiazine-6-thione 
• 125231-86-9 2-(4-Chloro-phenyl)-5-o-tolyl-[1,3,4]oxadiazolo[3,2-d][1,3,4]thiadiazine-6-thione 
• 125231-93-8 [2-(4-Chloro-phenyl)-[1,3,4]oxadiazolo[3,2-b][1,5,2]dithiazin-(6E)-ylidene]-p-tolyl-amine 
• 125231-92-7 [2-(4-Chloro-phenyl)-[1,3,4]oxadiazolo[3,2-b][1,5,2]dithiazin-(6E)-ylidene]-o-tolyl-amine 
• 1257542-59-8 4-(5-((5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)methylthio)-4-(2-chlorophenyl)-4H-1,2,4-triazol-3-yl)pyridine 

Relevant articles and documents

Synthesis and in vitro antiproliferative activity of new 1,3,4-oxadiazole derivatives possessing sulfonamide moiety

Synthesis of a new series of 1,3,4-oxadiazole derivatives possessing sulfonamide moiety is described. Their in vitro antiproliferative activities against NCI-58 human cancer cell lines of nine different cancer types were tested. Compound 1k with p-methoxybenzenesulfonamido moiety showed the highest mean %inhibition value over the 58 cell line panel at 10 μM concentration. It showed broad-spectrum antiproliferative activity over many cell lines of different cancer types. For instance, compound 1k inhibited the growth of T-47D breast cancer cell line by 90.47% at 10 μM. And it inhibited growth of SR leukemia, SK-MEL-5 melanoma, and MDA-MB-468 breast cancer cell lines by more than 80% at the same test concentration. Compound 1k showed superior activity than Paclitaxel and Gefitinib against the most sensitive cell lines.

Discovery of novel furo[2,3-d]pyrimidin-2-one–1,3,4-oxadiazole hybrid derivatives as dual antiviral and anticancer agents that induce apoptosis

A new series of furo[2,3-d]pyrimidine–1,3,4-oxadiazole hybrid derivatives were synthesized via an environmentally friendly, multistep synthetic tool and a one-pot Songoashira-heterocyclization protocol using, for the first time, nanostructured palladium pyrophosphate (Na2PdP2O7) as a heterogeneous catalyst. Compounds 9a–c exhibited broad-spectrum activity with low micromolar EC50 values toward wild and mutant varicella-zoster virus (VZV) strains. Compound 9b was up to threefold more potent than the reference drug acyclovir against thymidine kinase-deficient VZV strains. Importantly, derivative 9b was not cytostatic at the maximum tested concentration (CC50 > 100 μM) and had an acceptable selectivity index value of up to 7.8. Moreover, all synthesized 1,3,4-oxadiazole hybrids were evaluated for their cytotoxic activity in four human cancer cell lines: fibrosarcoma (HT-1080), breast (MCF-7 and MDA-MB-231), and lung carcinoma (A549). Data showed that compound 8f exhibits moderate cytotoxicity, with IC50 values ranging from 13.89 to 19.43 μM. Besides, compound 8f induced apoptosis through caspase 3/7 activation, cell death independently of the mitochondrial pathway, and cell cycle arrest in the S phase for HT1080 cells and the G1/M phase for A549 cells. Finally, the molecular docking study confirmed that the anticancer activity of the synthesized compounds is mediated by the activation of caspase 3.

Design, synthesis, and evaluation of N-benzylpyrrolidine and 1,3,4-oxadiazole as multitargeted hybrids for the treatment of Alzheimer's disease

Novel N-Benzylpyrrolidine hybrids were designed, synthesized, and tested against multiple in-vitro and in-vivo parameters. Among all the synthesized molecules, 8f and 12f showed extensive inhibition against beta-secretase-1 (hBACE-1), human acetylcholinesterase (hAChE) & human butyrylcholinesterase (hBuChE). These molecules are also endowed with significant AChE-peripheral anionic site (PAS) binding capability, blood-brain barrier permeability, potential disassembly of Aβ aggregates along with neuroprotection ability on SHSY-5Y cell lines. Results of the Y-Maze and Morris water maze test concluded that compounds 8f and 12f ameliorated cognitive dysfunction induced by scopolamine and Aβ. The ex-vivo activity was executed on rat's brain homogenate indicating a reduction in AChE level and oxidative stress. The pharmacokinetic investigation ascertained considerable oral absorption profile of the lead 12f. The results of the in silico docking studies and molecular dynamics simulations demonstrated stable interactions of compounds 8f and 12f with the target residues of hAChE, hBuChE and hBACE-1.

Oxazole ring-containing honokiol thioether derivative and preparation method and application thereof

The invention discloses an oxazole ring-containing honokiol thioether derivative, a preparation method thereof and application of the oxazole ring-containing honokiol thioether derivative as an alpha-glucosidase inhibitor, the chemical structure of the oxazole ring-containing honokiol thioether derivative is shown as a general formula (I), and R is selected from non-substituted or substituted phenyl. Compared with the prior art, the invention provides the novel honokiol thioether derivative containing the oxazole ring, and the honokiol thioether derivative containing the oxazole ring has good inhibitory activity on alpha-glucosidase, provides more possibilities for treating diabetes, and is expected to be used for preparing novel candidate drug molecules for treating diabetes. In addition, the preparation process is simple, the cost is low, and the yield is high.