1612-76-6

Basic information

• Product Name: 5-PHENYL-1,3,4-OXADIAZOL-2-AMINE
• Synonyms: 5-PHENYL-1,3,4-OXADIAZOL-2-AMINE;AKOS BBS-00006613;2-AMINO-5-PHENYL-1,3,4-OXADIAZOLE;1,3,4-OXADIAZOL-2-AMINE, 5-PHENYL-;AURORA KA-7809;TIMTEC-BB SBB000136;2-fenil-5-amino-1,3,4-ossadiazolo;4-oxadiazole,2-amino-5-phenyl-3
• CAS NO: 1612-76-6
• Molecular Formula: C₈H₇N₃O
• Molecular Weight: 161.16
• Mol File: 1612-76-6.mol

Chemical Properties

• Melting Point: 237-242°C
• Boiling Point: 332.3 °C at 760 mmHg
• Flash Point: 154.7 °C
• Appearance: WHITE TO TAN POWDER, CRYSTALS OR CRYSTALLINE. POWDER AND/OR CHUNKS
• Density: 1.276 g/cm³
• Vapor Pressure: 0.000148mmHg at 25°C
• Refractive Index: 1.606
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -1.15±0.13(Predicted)
• CAS DataBase Reference: 5-PHENYL-1,3,4-OXADIAZOL-2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-PHENYL-1,3,4-OXADIAZOL-2-AMINE(1612-76-6)
• EPA Substance Registry System: 5-PHENYL-1,3,4-OXADIAZOL-2-AMINE(1612-76-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: RO0620000
• HazardClass: IRRITANT
• Hazardous Substances Data: 1612-76-6(Hazardous Substances Data)

Usage

Uses

Used in Biomedical Applications:
5-PHENYL-1,3,4-OXADIAZOL-2-AMINE is used as a pH indicator for living cells in the acidic range due to the fluorescence it emits when in an acidic environment. This property makes it a valuable tool for monitoring and studying cellular processes, particularly those involving changes in pH levels.
Used in Analytical Chemistry:
In the field of analytical chemistry, 5-PHENYL-1,3,4-OXADIAZOL-2-AMINE can be employed as a fluorescent probe for detecting and measuring acidity in various samples. Its sensitivity to pH changes allows for accurate and reliable measurements, making it a useful addition to the chemist's toolbox.
Used in Material Science:
The compound's fluorescence properties can also be harnessed in material science for the development of new materials with specific optical or sensing properties. These materials could have applications in various industries, such as electronics, where they could be used in the creation of sensors or display technologies.
Used in Pharmaceutical Research:
5-PHENYL-1,3,4-OXADIAZOL-2-AMINE may also hold potential in the pharmaceutical industry, particularly in the development of new drugs or drug delivery systems. Its unique structure and properties could be exploited to design molecules with specific biological activities or to improve the delivery and efficacy of existing drugs.

InChI:InChI=1/C8H7N3O/c9-8-11-10-7(12-8)6-4-2-1-3-5-6/h1-5H,(H2,9,11)

Upstream product

• 1574-10-3 benzaldehyde semicarbazone 
• 7788-14-9 5-phenyl-1,2,4-oxadiazol-3-amine 
• 98-88-4 benzoyl chloride 
• 563-41-7 semicarbazide hydrochloride 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 4474-10-6 benzylidene-carbazic acid 
• 5351-66-6 benzoyl thiosemicarbazide 
• 1518-16-7 7,7',8,8'-tetracyanoquinodimethane 
• 109142-17-8 bis(C-phenyl-N-ureido)fomimidoyl disulphide 
• 4426-72-6 hydrazine carboxamide 
• 613-94-5 benzoic acid hydrazide 
• 104619-51-4 di(1H-imidazol-1-yl)methanimine 
• 199339-09-8 5-Phenyl-2-[(Z)-5-phenyl-[1,3,4]oxadiazol-2-ylimino]-thiazolidin-4-one 

Downstream Products

• 108790-04-1 5-phenyl-2-sulphinylamino-1,3,4-oxadiazole 
• 78078-00-9 N-Lithium-2-amino-5-phenyl-1,3,4-Oxadiazol 
• 69982-13-4 (5-phenyl-[1,3,4]oxadiazol-2-yl)-(triphenyl-λ⁵-phosphanylidene)-amine 
• 17703-73-0 6-Carbethoxy-5(H)-oxo-2-phenyl-1,3,4-oxadiazolo<4,5-a>pyrimidine 
• 135790-28-2 N-(2-Methyl-4-oxo-4H-quinazolin-3-yl)-2-(5-phenyl-[1,3,4]oxadiazol-2-ylamino)-acetamide 
• 80691-87-8 2-Phenyl-benzo[4,5]imidazo[2,3-b][1,3,4]oxadiazol-6-ol 
• 91036-53-2 5-Carbethoxy-2-phenyl-1,3,4-oxadiazolo<3,2-a>pyrimidin-7(H)-one 
• 118148-04-2 2-{[(E)-5-Phenyl-[1,3,4]oxadiazol-2-ylimino]-methyl}-benzoic acid 
• 92537-57-0 2,5-Diphenyl-1,3,4-oxadiazolo<3,2-a>pyrimidin-7(H)-one 
• 89757-60-8 3-Chloro-N-(5-phenyl-[1,3,4]oxadiazol-2-yl)-propionamide 
• 131548-02-2 N-(5-phenyl-1,3,4-oxadiazol-2-yl)acrylamide 
• 131548-13-5 2--5-phenyl-1,3,4-oxadiazole 
• 118148-03-1 [1-(2-Methoxy-phenyl)-meth-(E)-ylidene]-(5-phenyl-[1,3,4]oxadiazol-2-yl)-amine 
• 344870-25-3 2-Phenyl-2-(5-phenyl-[1,3,4]oxadiazol-2-ylamino)-propionitrile 

Relevant articles and documents

Synthesis of 2-amino-5-substituted-1,3,4-oxadiazoles using 1,3-dibromo-5,5-dimethylhydantoin as oxidant

A scalable synthesis of 5-substituted-2-amino-1,3,4-oxadiazoles via oxidation of a thiosemicarbazide precursor is described. The thiosemicarbazide intermediates are easily accessed from the corresponding acid chlorides. Oxidative cyclization using 1,3-dibromo-5,5-dimethylhydantoin as the primary oxidant, in the presence of potassium iodide, gives a variety of oxadiazoles in good yields. This methodology utilizes a commercially inexpensive and easily handled oxidant.

Photoinduced molecular rearrangements. Some comments on the ring-photoisomerization of 1,2,4-oxadiazoles into 1,3,4-oxadiazoles

The ring-photoisomerization of 3-amino- and 3-methylamino-5-phenyl-1,2,4-oxadiazoles into the corresponding 2-amino- and 2-methylamino-5-phenyl-1,3,4-oxadiazoles has been reinvestigated by examining the effect of a base on the photoreaction. On irradiatin

Synthesis of N,N-Disubstituted 3-amino- 1,2,4-triazoles

A general method for the synthesis of N,N-disubstituted 3-amino-l,2,4-triazoles 5 from di(benzotriazolyl)methanimines 1 and 1′, hydrazine and substituted hydrazines is developed. The desired compounds were prepared regioselectively under mild conditions b

Chlorination and subsequent cyclization to 1,3,4-oxadiazoles of N1-acyl-N3-cyanoguanidines and rerated compounds

N1-Acyl-, N1-alkoxycarbonyl-, and N1-(N,N-dialkylcarbamoyl)guanidines bearing electron-withdrawing cyano or sulfonyl group at the N3-position were found to provide corresponding rearranged products, 1,3,4-oxadiazoles, when these guanidines were chlorinated by sodium hypochlorite followed by treating with base. Assignments of obtained compounds were accomplished by means of some reactions such as acid hydrolysis, alkoholysis, and catalytic hydrogenations, and of MS spectra.

N,N-dialkyl-N′-chlorosulfonylchloroformamidines in heterocyclic synthesis. II. Thiazolo-, thiadiazolo-, and oxadiazolo-fused [1,2,4,6]thiatriazine dioxides

N,N-dialkyl-N′-chlorosulfonylchloroformamidines 1 were treated with 2-aminothiazoline, 2-aminothiazoles, 2-aminobenzothiazoles, 2-amino-1,3,4- thiadiazoles, and 2-amino-1,3,4-oxadiazoles to give a 6,7-dihydrothiazolo[3,2-b] [1,2,4,6]thiatriazine dioxide 3

Synthesis, telomerase inhibitory and anticancer activity of new 2-phenyl-4H-chromone derivatives containing 1,3,4-oxadiazole moiety

Based on previous studies, 66 2-phenyl-4H-chromone derivatives containing amide and 1,3,4-oxadiazole moieties were prepared as potential telomerase inhibitors. The results showed most of the title compounds exhibited significantly inhibitory activity on telomerase. Among them, some compounds demonstrated the most potent telomerase inhibitory activity (IC50 50 = 6.41 μM). In addition, clear structure–activity relationships were summarised, indicating that the substitution of the methoxy group and the position, type and number of the substituents on the phenyl ring had significant effects on telomerase activity. Among them, compound A33 showed considerable inhibition against telomerase. Flow cytometric analysis showed that compound A33 could arrest MGC-803 cell cycle at G2/M phase and induce apoptosis in a concentration-dependent way. Meanwhile, Western blotting revealed that this compound could reduce the expression of dyskerin, which is a fragment of telomerase.

Synthesis and anticonvulsant evaluation of indoline derivatives of functionalized aryloxadiazole amine and benzothiazole acetamide

A series of N-(substituted benzothiazole-2-yl)-2-(2,3-dioxoindolin-1-yl)acetamide (4a-i) and substituted-[3-((5-phenyl-1,3,4-oxadiazole-2-yl)imino)indolene-2-one] (5a-f) were designed, synthesized fulfilling the structural requirement of pharmacophore and evaluated for anticonvulsant activities using maximal electroshock test (MES), subcutaneous pentylenetetrazole (scPTZ) seizures and neurotoxicity by motor impairment model in mice. The most active compoundN-(5-chlorobenzo[d]thiazol-2-yl)-2-(2,3-dioxoindolin-1-yl)acetamide (4a) has shown significant anticonvulsant activity against both MES and scPTZ screens and emerged as most effective anticonvulsant compound with median dose of 35.7 mg/kg (MES ED50), 88.15 mg/kg (scPTZ ED50) and toxic dose (TD50) was found to be > 500mg/kg. In silico studies including molecular docking study was carried to establish the molecular interaction of potent compound (4a) in both Na+ channel and GABAA receptors. The prediction of pharmacokinetic parameters and distance mapping of compounds were also performed to establish the drug likeness property.

Synthesis, antibacterial activities and molecular docking study of thiouracil derivatives containing oxadiazole moiety

A series of novel thiouracil derivatives 9 containing an oxadiazole moiety have been synthesized by structural modification of a lead SecA inhibitor, 2. These compounds have been evaluated for their antibacterial activities against Bacillus amyloliquefaciens, Staphylococcus aureus and Bacillus subtilis. Among them, compounds 9g and 9n exhibited promising antibacterial activities against the tested strains. Compound 9g was also tested for its inhibitory activities against SecA ATPase, and the IC50 value of compound 9g was 19.9 μg/mL, lower than that of compound 2 (20.8 μg/mL). Molecular docking work indicates that compound 9g likely occupies the pocket formed by SecA IRA2 and NBD domain.

Synthesis of 1,3,4-oxadiazoles as selective T-type calcium channel inhibitors

– Neuropathic pain, epilepsy, insomnia, and tremor disorder may arrive from an increase of intracellular Ca2+ concentration through a dysfunction of T-type Ca2+ channels. Thus, T-type calcium channels could be a target in drug discovery for the treatments of neuropathic pain and epilepsy. From rational drug design approach, a group of 2,5-disubstituted 1,3,4-oxadiazole molecules was synthesized and their selective T-type channel inhibitions were evaluated. The synthetic strategy consists of a short sequence of three reactions: (i) condensation of thiosemicarbazide with acid chlorides; (ii) ring closing by 1,3-dibromo-5,5-dimethylhydantoin; and (iii) coupling with various acid chlorides. 5-Chloro-N-(5-phenyl-1,3,4-oxadiazol-2-yl)thiophene-2-carboxamide (11) was found to selectively inhibit T-type Ca2+ channel over Na+ and K+ channels in mouse dorsal root ganglion neurons and/or human embryonic kidney (HEK)-293 cells and to suppress seizure-induced death in mouse model. Consequently, compound 11 is a useful probe for investigation of physiologic and pathophysiologic roles of the T-channel, and provides a basis to develop a novel therapeutic to treat chronic neuropathic and inflammatory pains.

CF3-, OCF3-, SCF3- AND SF5-CONTAINING ANTIBACTERIAL AGENTS

The present invention generally relates to compounds as a new antibiotic to treat various infections, including infections caused by methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-intermediate and vancomycin-resistant S. aureus (VISA and VRSA respectively) vancomycin-resistant Enterococcus faecalis (VRE), and Clostridioides difficile. Pharmaceutical compositions and methods for treating those infection diseases are within the scope of this invention.