288-99-3 Usage
Description
1,3,4-Oxadiazole is a five-membered, conjugated, planar, stable heteroaromatic compound, consisting of two adjacent nitrogen atoms at the 3,4-positions with one oxygen atom and two vicinal carbon atoms. Each nitrogen atom in the ring is one carbon apart from the oxygen heteroatom. The 1,3,4-oxadiazole ring is electron deficient due to the presence of two pyridine-like nitrogen atoms in the ring, resulting in chemical properties that are distinct from those of furan. It is a significant molecule in medicinal chemistry, acting as a surrogate for carboxylic acids, esters, and carboxamides, and exhibiting a broad spectrum of pharmacological activities.
Uses
Used in Pharmaceutical Industry:
Oxdiazole is used as a therapeutic agent for its antibacterial, anti-mycobacterial, antitumor, antiviral, and antioxidant activities. It modulates various biological pathways and demonstrates synergistic effects when combined with conventional drugs, enhancing their efficacy and sensitivity.
Used in Chemical Industry:
Oxdiazole is used as a building block in the synthesis of various compounds due to its electron-deficient nature and diverse pharmacological properties.
Used in Pesticide Industry:
Oxdiazole derivatives, such as oxadiazolinones, are used as insecticides and herbicides, providing effective pest control.
Used in Diagnostic Industry:
One of the oxadiazole derivatives, (2-[4-biphenylyl]-5-[4-tert-butylphenyl])-1,3,4-oxadiazole, is used as a scintillator in diagnostic applications.
Used in Optoelectronics Industry:
2,5-Disubstituted-1,3,4-oxadiazoles are used in the development of laser dyes, optical brighteners, scintillators, and electrophotographic photoconductors due to their fluorescence properties.
Used in Explosives Industry:
2,5-Dipicryl-1,3,4-oxadiazole has been reported as an explosive, showcasing its potential in this field.
Used in Corrosion Inhibition:
2-Aryl-5-oxadiazoline-5-thiones are used to inhibit corrosion in mild steel by acid solutions, providing protection against wear and tear.
Used in Liquid Crystal Industry:
A series of liquid crystals based on 1,3,4-oxadiazoles have been prepared and used to study the flexoelectric effect in guest/host mixtures, contributing to the advancement of liquid crystal technology.
Preparation
A solution of potassium hydroxide (4 pellets) was made in absolute ethanol (40ml) & poured into a round bottom flask. 10g of prepared hydrazide and 10ml of carbon disulphide was added in the round bottom flask. Condenser was adjusted and allowed to reflux for 6-8 hours. Reaction progress was checked at regular intervals by using TLC procedure with the use of varying ratio of n-hexane & ethyl acetate. As the reaction got completed, 20ml of chilled distilled water and a very small amount of dil. Sulfuric acid (H2SO4) to maintain the pH 2-3 in order to remove un-reacted base. Solid precipitates were obtained on vigorous shaking and filtered. Product was dried, collected &calculated.
Chemical Reactivity
Electrophilic substitution to 1,3,4-oxadiazole is unusual because electron density at the C2-and C5-positions is low. Electrophilic substitution is facile in aryl group present as substituent in lieu of 1,3,4-oxadiazole ring. Nucleophilic substitution reactions are uncommon in 1,3,4-oxadiazoles but ring cleavage is very common.
Check Digit Verification of cas no
The CAS Registry Mumber 288-99-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,8 and 8 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 288-99:
(5*2)+(4*8)+(3*8)+(2*9)+(1*9)=93
93 % 10 = 3
So 288-99-3 is a valid CAS Registry Number.
InChI:InChI=1/C2H2N2O/c1-3-4-2-5-1/h1-2H
288-99-3Relevant articles and documents
Functionalization of 1,3,4-Oxadiazoles and 1,2,4-Triazoles via Selective Zincation or Magnesiation Using 2,2,6,6-Tetramethylpiperidyl Bases
Schw?rzer, Kuno,Tüllmann, Carl Phillip,Gra?l, Simon,Górski, Bartosz,Brocklehurst, Cara E.,Knochel, Paul
supporting information, p. 1899 - 1902 (2020/03/03)
We report the metalation of the 1,3,4-oxadiazole and 1,2,4-triazole scaffolds via regioselective zincation or magnesiation using the TMP bases (TMP = 2,2,6,6-tetramethylpiperidyl) TMP2Zn·2LiCl, TMP2Zn·2MgCl2·2LiCl, TMPMgCl
Improved synthesis and characterisation of 1,3,4-oxadiazole
Aitken, Kati M.,Aitken, R. Alan
experimental part, p. 75 - 79 (2012/03/10)
Synthetic approaches to 1,3,4-oxadiazole have been investigated and an improved method involving dehydration of N,N′-diformylhydrazine with P2O5 in polyphosphoric acid is described. The 13C NMR spectrum of this compound is reported for the first time including determination of 1JC-H and 3J C-H. ARKAT-USA, Inc.
Substituted amino methyl factor Xa inhibitors
-
, (2008/06/13)
The present application describes substituted-aminomethyl substituted compounds and derivatives thereof, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of factor Xa.
