10600-83-6

Basic information

• Product Name: 2,5-BIS(4-HYDROXYPHENYL)-1,3,4-OXADIAZOLE
• Synonyms: 2,5-BIS(4-HYDROXYPHENYL)-1,3,4-OXADIAZOLE;4-[5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]phenol;Phenol, 4,4'-(1,3,4-oxadiazole-2,5-diyl)bis-
• CAS NO: 10600-83-6
• Molecular Formula: C₁₄H₁₀N₂O₃
• Molecular Weight: 254.24
• Product Categories: pharmacetical
• Mol File: 10600-83-6.mol

Chemical Properties

• Boiling Point: 501.2°Cat760mmHg
• Flash Point: 256.9°C
• Appearance: /
• Density: 1.366g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.648
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,5-BIS(4-HYDROXYPHENYL)-1,3,4-OXADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-BIS(4-HYDROXYPHENYL)-1,3,4-OXADIAZOLE(10600-83-6)
• EPA Substance Registry System: 2,5-BIS(4-HYDROXYPHENYL)-1,3,4-OXADIAZOLE(10600-83-6)

Safety Data

• Hazardous Substances Data: 10600-83-6(Hazardous Substances Data)

Usage

Uses

Used in Plastics Industry:
2,5-BIS(4-HYDROXYPHENYL)-1,3,4-OXADIAZOLE is used as a key component in the production of various types of plastics for its ability to enhance thermal stability, ensuring that the final products can resist high temperatures.
Used in Adhesives Industry:
In the adhesives industry, 2,5-BIS(4-HYDROXYPHENYL)-1,3,4-OXADIAZOLE is employed as a critical ingredient to improve the adhesive's performance, particularly in high-temperature environments where conventional adhesives may fail.
Used in Thermal Paper Production:
2,5-BIS(4-HYDROXYPHENYL)-1,3,4-OXADIAZOLE is used as a crucial additive in the manufacturing of thermal paper, which is designed to change color when exposed to heat, commonly used in receipts and other heat-sensitive documents.
Given the health concerns associated with bisphenol O, there is a growing push to identify and develop alternative materials and chemicals that can safely replace it in these and other industrial applications. This is driven by a need to mitigate the potential risks to human health and the environment while maintaining the performance characteristics required for these products.

InChI:InChI=1/C14H10N2O3/c17-11-5-1-9(2-6-11)13-15-16-14(19-13)10-3-7-12(18)8-4-10/h1-8,17-18H

Upstream product

• 17696-62-7 Phenyl 4-hydroxybenzoate 
• 5351-23-5 4-hydroxybenzoic acid hydrazide 
• 99-96-7 4-hydroxy-benzoic acid 
• 41097-49-8 p-hydroxybenzaldehyde azine 
• 847-39-2 2,5-bis(4-methoxyphenyl)-1,3,4-oxadiazole 
• 100872-56-8 4-hydroxy-[(4-hydroxyphenyl)methylidene]benzohydrazide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 100-09-4 4-methoxybenzoic acid 
• 43100-26-1 N,N'-bis(p-hydroxybenzoyl)hydrazine 
• 100-07-2 4-methoxy-benzoyl chloride 
• 3290-99-1 4-methoxybenzoic acid hydrazide 
• 94-30-4 ethyl 4-methoxybenzoate 

Downstream Products

• 1000402-00-5 2-(4-undecyloxyphenyl)-5-(4-hydroxyphenyl)-[1,3,4]-oxadiazole 
• 1000402-03-8 2-[4-(4-undecyloxyphenylcarbonyloxy)phenyl]-5-(4-hydroxyphenyl)-[1,3,4]-oxadiazole 
• 1219463-66-7 2,5-bis-(4-undecyloxyphenylcarbonyloxyphenyl)[1,3,4]oxadiazole 
• 1219463-59-8 2,5-bis-{4-[4-octyloxy2-(pent-4-enyloxy)phenylcarbonyloxy]phenyl}[1,3,4]oxadiazole 
• 1154855-14-7 OC₄-2MePh(ODBP) 
• 1154855-25-0 OC₁₂-2MePh(ODBP) 
• 1154855-41-0 OC₁₂-3MePh(ODBP) 
• 1154855-33-0 2,5-bis-(4-(4-butoxy-3-methylbenzoyloxy)-phenyl)-1,3,4-oxadiazole 

Relevant articles and documents

Synthesis of 1,3,4-oxadiazole and xanthen-2-one luminophoric epoxide monomers

Epoxide derivatives of 2,5-bis-oxyphenyl-1,3,4-oxadiazoles and fluorescein, which are luminescent epoxide monomers, are synthesized. Their luminescence properties are studied. 1999 KluwerAcademic/Plenum Publishers.

Synthesis, liquid-crystalline, photophysical and chemosensor properties of oxadiazole/thiadiazole-based amphiphiles with glycerol groups

Two series of heterocycle-based mesogens consisting of a long 2,5-diphenyl-1,3,4-oxadiazole/thiadiazole rigid core with three lipophilic and flexible alkyl chains at one end and a polar glycerol group at the opposite end have been synthesized via one pot cyclization reaction. These compounds were investigated by polarizing optical microscopy (POM), differential scanning calorimetry (DSC), X-ray scattering, cyclic voltammetry, UV–vis spectroscopy and photoluminescence measurements. Upon elongation of the alkyl chains, a transition from hexagonal columnar phase to Pm3ˉn-type cubic phase was observed in both series. Oxadiazole series are blue luminescent LCs with binding selectivity to Li+, while thiadiazole series are blue-green luminescent LCs with binding selectivity to Fe3+.

Rapid synthesis of 2,5-disubstituted 1,3,4-oxadiazoles under microwave irradiation

A number of symmetrically 2,5-disubstituted 1,3,4-oxadiazoles are quickly prepared by the reaction of aromatic acids with hydrazine dihydrochloride in a mixture of orthophosphoric acid and phosphorus pentoxide under microwave irradiation.

Oxidative cyclization of aldazines with bis(trifluoroacetoxy)iodobenzene

Symmetrical and unsymmetrical aldazines are efficiently converted to 2,5-disubstituted-1,3,4-oxadiazoles by oxidation with bis(trifluoroacetoxy) iodobenzene (BTI).

Study of heterogeneous catalysis by iron-squarate based 3d metal organic framework for the transformation of tetrazines to oxadiazole derivatives

We present here a simple, milder, and environmentally benign heterogeneous catalytic method for the transformation of tetrazines to oxadiazole derivatives at room temperature (25 °C) using our earlier synthesized iron-squarate based 3D metal organic framework, [Fe3(OH)3(C 4O4)(C4O4)0.5] n (FeSq-MOF).

The effects of asymmetric bent-shaped compounds on the temperature range and electro-optical performances of liquid crystalline blue phases

A series of asymmetric and symmetric bent-shaped molecules with branched terminals were synthesized and characterized. Their effects on inducing blue phase and electro-optical performances were compared and analyzed experimentally. It was found that the asymmetric and symmetric compounds almost have the same effect on inducing and stabilizing blue phase, but the electro-optical performance of mixtures doped with asymmetric compounds are much better than that of mixtures doped with symmetric compounds for they have a totally different dielectric anisotropy which can contribute to a larger Kerr constant.

Electrochemical oxidation of aldehyde-N-arylhydrazones into symmetrical-2,5-disubstituted-1,3,4-oxadiazoles

A convenient, efficient and one-pot synthesis of chemically and pharmaceutically interesting symmetrical-2,5-disubstituted-1,3,4-oxadiazoles is reported. The protocol involves anodic oxidation of aldehyde-N-arylhydrazones in anhyd. MeCN-LiClO4. Constant potential electrolysis carried out in an undivided cell and platinum electrodes leads to the formation of the corresponding oxadiazoles under ambient condition and the mechanism was deduced from voltammetry studies. The reaction proceeded smoothly with high atom economy. Springer Science+Business Media Dordrecht 2013.

Electrosynthesis and screening of novel 1,3,4-oxadiazoles as potent and selective antifungal agents

The electrochemical oxidation of aldehyde-N-aroylhydrazone has been studied in the presence of NaClO4 as supporting electrolyte in MeOH solution using cyclic voltammetry and controlled potential electrolysis. The results indicate that intramolecular cyclization of aldehyde-N-aroylhydrazone has been successfully performed at a platinum electrode in an undivided cell with good yields of the corresponding 1,3,4-oxadiazoles at ambient conditions. The reaction products were characterized by spectroscopic methods and a mechanism was deduced from voltammetry studies. The antifungal activity of the synthesized compounds was evaluated on Fusarium oxysporum, Alternaria solani, Candida albicans and Aspergillus niger. The results revealed that all the synthesized compounds have significant antifungal activity against the tested fungi. Among the synthesized derivatives 7b, 7d, 7g, 7h, 7i, 7j and 7r were found to be the most effective antifungal compounds. The Royal Society of Chemistry 2013.

Bent-core systems based on [1,3,4]oxadiazole core with shape biaxiality

The present paper is presenting the Synthesis and characterization of new [1,3,4]oxadiazole derivatives obtained by attaching different mesogenic units to the central core. Liquid crystals properties analysis by POM and DSC techniques is presented and structure-properties correlations are discussed.