49787-02-2

Basic information

• Product Name: 4-(5-METHYL-1,2,4-OXADIAZOL-3-YL)PHENOL
• Synonyms: 4-(5-methyl-1,2,4-oxadiazol-3-yl)phenol(SALTDATA: FREE)
• CAS NO: 49787-02-2
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.172
• Mol File: 49787-02-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 227.9°Cat760mmHg
• Flash Point: 91.6°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: 4-(5-METHYL-1,2,4-OXADIAZOL-3-YL)PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(5-METHYL-1,2,4-OXADIAZOL-3-YL)PHENOL(49787-02-2)
• EPA Substance Registry System: 4-(5-METHYL-1,2,4-OXADIAZOL-3-YL)PHENOL(49787-02-2)

Safety Data

• Hazardous Substances Data: 49787-02-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H8N2O2/c1-6-10-9(11-13-6)7-2-4-8(12)5-3-7/h2-5,12H,1H3

Upstream product

• 49787-00-0 N',4-dihydroxybenzamidine 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 49787-00-0 N,4-dihydroxybenzene-1-carboxyimidamide 
• 5311-71-7 methyl 4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl ether 
• 5373-87-5 4-methoxybenzamidoxime 
• 874-90-8 4-methoxybenzonitrile 
• 767-00-0 4-cyanophenol 
• 1219626-47-7 (Z)-N',4-dihydroxybenzimidamide 
• 95124-68-8 5-methyl-3-(4-carboxyphenyl)-1,2,4-oxadiazole 

Downstream Products

• 49787-07-7 2-methyl-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenoxy]-propionic acid 
• 144797-44-4 5-Methyl-3-(4-oxiranylmethoxy-phenyl)-[1,2,4]oxadiazole 
• 634610-96-1 2-O-[4'-(5''-methyl[1,2,4]oxadiazol-3''-yl)phenyl]-5-O-[4'''-(2''''-methylsulfonylphenyl)phenyl]-1,4:3,6-dianhydro-D-sorbitole 
• 745794-66-5 2-O-[4'-(5''-methyl[1,2,4]oxadiazol-3''-yl)phenyl]-5-O-[4'''-(piperidin-2''''-on-1''''-yl)phenyl]-1,4:3,6-dianhydro-D-sorbitole 
• 745794-60-9 2-O-[4'-(5''-methyl[1,2,4]oxadiazol-3''-yl)phenyl]-5-O-[3''''-(2''''-tert-butylaminosulfonylphenyl)phenyl]-1,4:3,6-dianhydro-D-sorbitole 
• 745794-63-2 2-O-[4'-(5''-methyl[1,2,4]oxadiazol-3''-yl)phenyl]-5-O-[4'''-(2''''-tert-butylaminosulfonylphenyl)benzyl]-1,4:3,6-dianhydro-D-sorbitole 
• 144797-24-0 1-Isopropylamino-3-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenoxy]-propan-2-ol 
• 144797-27-3 1-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-3-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenoxy]-propan-2-ol 
• 144797-28-4 1-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-3-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenoxy]-propan-2-ol 
• 1196485-57-0 4-{4-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenoxy]-pyrazolo[3,4-d]pyrimidin-1-yl}-piperidine-1-carboxylic acid tert-butyl ester 
• 1204309-48-7 1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-4-{3-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenoxy]propyl}piperidine 
• 1341223-02-6 3-methyl-6-(3-{[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]methyl}azetidin-1-yl)pyridazine 

Relevant articles and documents

Decarboxylative Hydroxylation of Benzoic Acids

Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35 °C via photoinduced ligand-to-metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late-stage applications.

3-Aryl-1,2,4-oxadiazole Derivatives Active Against Human Rhinovirus

The human rhinovirus (hRV) is the causative agent of the common cold that often aggravates respiratory complications in patients with asthma or chronic obstructive pulmonary disease. The high rate of mutations and variety of serotypes are limiting the development of anti-hRV drugs, which emphasizes the need for the discovery of novel lead compounds. Previously, we identified antiviral compound 1 that we used here as the starting material for developing a novel compound series with high efficacy against hRV-A and -B. Improved metabolic stability was achieved by substituting an ester moiety with a 1,2,4-oxadiazole group. Specifically, compound 3k exhibited a high efficacy against hRV-B14, hRV-A21, and hRV-A71, with EC50 values of 66.0, 22.0, and 3.7 nM, respectively, and a relevant hepatic stability (59.6 and 40.7% compound remaining after 30 min in rat and human liver microsomes, respectively). An in vivo study demonstrated that 3k possessed a desirable pharmacokinetic profile with low systemic clearance (0.158 L·h-1·kg-1) and modest oral bioavailability (27.8%). Hence, 3k appears to be an interesting candidate for the development of antiviral lead compounds.

Progress in the proxifan class: heterocyclic congeners as novel potent and selective histamine H3-receptor antagonists

Histamine H3 receptors are critically involved in the pathophysiology of several disorders of the central nervous system (CNS). Among other families of H3-receptor ligands, the proxifan class has recently been described to contain numerous potent histamine H3-receptor antagonists, e.g. ciproxifan or imoproxifan. In the present study, we report on the design of novel heterocyclic proxifan analogues and their antagonist potencies at histamine H3 receptors. The new compounds were tested for in vitro and in vivo H3-receptor antagonist potencies in different species as well as for H3-receptor selectivity vs. H1 and H2 receptors. In vitro, all compounds investigated proved to be potent H3-receptor antagonists in the rat as well as in the guinea-pig. In addition, they showed good to high oral CNS potency in vivo in mice. Especially, oxadiazole derivatives 24-26 displayed nanomolar antagonist activity in vitro and high potency in vivo (ED50=0.47-0.57 mg/kg). The results show that the additional heteroaromatic moieties might act as bioisosteres of the ketone or oxime moieties of ciproxifan or imoproxifan, respectively, and might cause divergent pharmacokinetic properties. Thus, these novel H3-receptor antagonists are interesting leads for further development. Copyright