1456-22-0

Basic information

• Product Name: 3-phenyl-1,2,4-oxadiazol-5(4H)-one
• Synonyms: 3-phenyl-1,2,4-oxadiazol-5(4H)-one;3-Phenyl-4,5-dihydro-1,2,4-oxadiazole-5-one;3-phenyl-1,2,4-oxadiazol-5-ol;1,2,4-Oxadiazol-5(2H)-one, 3-phenyl-;1,2,4-Oxadiazol-5(4H)-one, 3-phenyl-;3-phenyl-2H-1,2,4-oxadiazol-5-one;3-phenyl-1,2,4-Oxadiazol-5(2H)-one;3-phenyl-5-hydroxy-1,2,4-oxadiazole
• CAS NO: 1456-22-0
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.14544
• EINECS: 215-938-8
• Mol File: 1456-22-0.mol
• Article Data: 26

Chemical Properties

• Melting Point: 198 °C
• Boiling Point: 237.1°C at 760 mmHg
• Flash Point: 97.2°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 0.0457mmHg at 25°C
• Refractive Index: 1.646
• Storage Temp.: 2-8°C
• PKA: 7.13±0.20(Predicted)
• CAS DataBase Reference: 3-phenyl-1,2,4-oxadiazol-5(4H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-1,2,4-oxadiazol-5(4H)-one(1456-22-0)
• EPA Substance Registry System: 3-phenyl-1,2,4-oxadiazol-5(4H)-one(1456-22-0)

Safety Data

• Hazardous Substances Data: 1456-22-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 30, p. 336, 1982 DOI: 10.1248/cpb.30.336

InChI:InChI=1/C8H6N2O2/c11-8-9-7(10-12-8)6-4-2-1-3-5-6/h1-5H,(H,9,10,11)

Upstream product

• 54752-10-2 N-ethoxycarbonyloxy-benzamidine 
• 32971-23-6 2-hydroxyimino-2-phenyl-acetohydroxamic acid 
• 54752-10-2 O-(ethoxycarbonyl)benzohydroxamamide 
• 125520-55-0 3-carboxy-4-phenyl-1,2,5-oxadiazole 2-oxide 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 1885-14-9 phenyl chloroformate 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 108-23-6 isopropyl chloroformate 
• 24608-52-4 tert-butyl chloroformate 
• 873-67-6 benzonitrile oxide 
• 186581-53-3 diazomethane 
• 1064700-71-5 2,2-dinitro-2-(3-phenyl-1,2,4-oxadiazol-5-yl)acetonitrile 
• 1064700-73-7 5-methyl-2H-1,2,3-triazol-4-yl(dinitro)(3-phenyl-1,2,4-oxadiazol-5-yl)methane 

Downstream Products

• 618-39-3 benzamidin 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 3201-46-5 4-methyl-3-phenyl-1,2,4-oxadiazol-5(4H)-one 
• 3201-47-6 3-phenyl-5-methoxy-1,2,4-oxadiazole 
• 14562-01-7 3,4-diphenyl-1,2,4-oxadiazol-5(4H)-one 
• 19226-11-0 4-mesityl-3-phenyl-1,2,4-oxadiazol-5(4H)-one 
• 1532-84-9 isoquinolin-1-ylamine 
• 1450630-89-3 2-{benzo[e][1,2,4]triazin-3-yl}phenyl acetate 
• 1450631-00-1 C₁₇H₁₃N₃O₄ 
• 81817-16-5 7-chloro-3-phenylbenzo[e][1,2,4]triazine 
• 81817-14-3 7-methyl-3-phenylbenzo[e][1,2,4]triazine 
• 120914-40-1 3-phenyl-6-(trifluoromethyl)benzo[e][1,2,4]triazine 
• 69918-17-8 6-bromo-3-phenylbenzo[e][1,2,4]triazine 
• 99768-31-7 6-chloro-3-phenylbenzo[e][1,2,4]triazine 

Relevant articles and documents

-

-

-

-

Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts

Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts under mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows utilizing both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). We found that the steric effects in aryl moieties determined the chemoselectivity of N- and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones. Mesityl-substituted diaryliodonium salts demonstrated the high potential as a selective arylation reagent. The structural study suggests that steric accessibility of N-atom in 1,2,4-oxadiazol-5(4H)-ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4-oxadiazol-2(3H)-ones and 1,2,4-oxadiazole-5-thiol. (Figure presented.).

Development of the 99mTc-Hydroxamamide Complex as a Probe Targeting Carbonic Anhydrase IX

Carbonic anhydrase IX (CA-IX) is regarded as a favorable target for in vivo imaging because of its specific expression in hypoxic regions of tumors. Hypoxia assists tumor propagation and growth and is resistant to chemotherapy and radiotherapy. Here, we designed and synthesized [99mTc]hydroxamamide ([99mTc]Ham) and [99mTc]methyl-substituted-hydroxamamide ([99mTc]MHam) complexes including a bivalent CA-IX ligand, sulfonamide (SA), and ureidosulfonamide (UR). In a cell binding assay, [99mTc]Ham complexes with bivalent SA ([99mTc]SAB2A and [99mTc]SAB2B) and UR ([99mTc]URB2A and [99mTc]URB2B) showed significantly greater uptake into CA-IX high-expressing (HT-29) cells than that into CA-IX low-expressing cells. Since the binding affinity of [99mTc]URB2A and [99mTc]URB2B for CA-IX was significantly higher than that of [99mTc]SAB2A and [99mTc]SAB2B, we additionally synthesized [99mTc]MURB2 (a [99mTc]MHam complex with bivalent UR) and evaluated the CA-IX-specific binding affinity of [99mTc]URB2A, [99mTc]URB2B, and [99mTc]MURB2. Their uptake into HT-29 cells was reduced by the addition of a CA inhibitor, acetazolamide, suggesting their CA-IX-specific binding affinity. A biodistribution study in HT-29 tumor-bearing mice was carried out using [99mTc]URB2A and [99mTc]MURB2 with the highest specificity for HT-29 cells. [99mTc]URB2A showed moderate tumor uptake and reduction by coinjection with acetazolamide; however, the tumor/blood ratio was insufficient for in vivo imaging. These results provided key information for the design of novel Ham-based imaging probes targeting CA-IX.