92-71-7 Usage
Chemical Properties
light beige solid
Uses
PPO can be used as a dopant that improves the photo-electric feedback of plastic scintillators which are used as radiation detectors for nuclear materials. It can be coated on peptide substrates to facilitate radioactive labelling which can enable determination of substrate specificity of lysine methyltransferase enzymes. It may also be used in the fabrication of organic luminescent materials which can be used in light emitting diodes (LEDs).
Synthesis Reference(s)
Journal of the American Chemical Society, 88, p. 1844, 1966 DOI: 10.1021/ja00960a066The Journal of Organic Chemistry, 36, p. 1937, 1971 DOI: 10.1021/jo00813a021
General Description
2,5-Diphenyloxazole (PPO) is an oxazole that can be used as a scintillator and a laser dye. It has fluorescence at a wavelength of 375 nm. It can be used as a wavelength shifter in liquid samples due to their high quantum yield and large strokes shift.
Hazard
May cause irritation
Synthesis
The synthesis of?2,5-Diphenyloxazole is as follows:In a 5000L enamel reactor with mechanical stirring and a thermometer, add benzoylaminoacetic acid (179 kg, 1 km) and thionyl chloride (238 kg, 2 km), react at 50°C, and monitor the sample until the compound is fully reacted. Unreacted thionyl chloride is distilled off to obtain benzoylaminoacetyl chloride. Cool down to 50°C, add benzene (780 kg, 10 kmol) to the reactor andAluminum trichloride (267 kg, 2 kmol), heated to reflux for 3 hours.The obtained N-benzoyl-ω-aminoacetophenone reaction solution was cooled to 30°C, 50 wt% sulfuric acid (392 kg, 2 kmol) was added, and the temperature was slowly raised to 100°C, and the reaction was completed at this temperature. Excess benzene was distilled off, the reaction solution was cooled to 30°C, water (1568 kg) was added dropwise to the reactor, and a white solid was precipitated, filtered, and rectified to obtain 2,5-diphenyloxazole of about 202 kg. The yield was 91.4%, the content was 99.3% (HPLC).
Purification Methods
Distil it in steam and crystallise it from ligroin. [Beilstein 27 III/IV 1437.]
Check Digit Verification of cas no
The CAS Registry Mumber 92-71-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 2 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 92-71:
(4*9)+(3*2)+(2*7)+(1*1)=57
57 % 10 = 7
So 92-71-7 is a valid CAS Registry Number.
InChI:InChI=1/C15H11NO/c1-3-7-12(8-4-1)14-11-16-15(17-14)13-9-5-2-6-10-13/h1-11H
92-71-7Relevant articles and documents
Thiocarbamate-directed Cp*Co(III)-Catalyzed Olefinic C?H Amidation: Facile Access to Enamines with High (Z)-Selectivity
Liang, Ya-Ru,Si, Xiao-Ju,Zhang, He,Yang, Dandan,Niu, Jun-Long,Song, Mao-Ping
, p. 694 - 700 (2021)
A thiocarbamate-directed Cp*Co(III)-catalyzed C?H oxidative amidation of olefins is achieved to synthesize a series of enamines. The key feature of this protocol is the use of earth-abundant cobalt as catalyst and thiocarbamate as directing group, which provides an efficient and simple manner to synthesize enamines in good yields with high (Z)-selectivity. This reaction proceeds smoothly under very mild conditions (rt and air), and a wide range of functionalized alkenes, as well as dioxazolones, were compatible with the standard reaction conditions.
Pd/Cu-Catalyzed C-H/C-H Cross Coupling of (Hetero)Arenes with Azoles through Arylsulfonium Intermediates
Lin, Zeng-Hui,Tian, Ze-Yu,Zhang, Cheng-Pan
supporting information, p. 4400 - 4405 (2021/06/27)
A highly efficient method for the selective formal C-H/C-H cross-coupling of azoles and (hetero)arenes was established through arylsulfonium intermediates under transition-metal catalysis, which produced a variety of 2-(hetero)aryl azoles in good to excellent yields. Advantages of the reaction included mildness, a good functional group tolerance, a wide range of substrates, a high regio- and chemoselectivity, one-pot procedures, and the late-stage functionalization of complex molecules without the use of oxidants, offering a promising strategy for the transition-metal-catalyzed C-H arylation of azoles.
Photoinduced Heterogeneous C?H Arylation by a Reusable Hybrid Copper Catalyst
Choi, Isaac,Müller, Valentin,Lole, Gaurav,K?hler, Robert,Karius, Volker,Vi?l, Wolfgang,Jooss, Christian,Ackermann, Lutz
supporting information, p. 3509 - 3514 (2020/03/03)
Heterogeneous copper catalysis enabled photoinduced C?H arylations under exceedingly mild conditions at room temperature. The versatile hybrid copper catalyst provided step-economical access to arylated heteroarenes, terpenes and alkaloid natural products with various aryl halides. The hybrid copper catalyst could be reused without significant loss of catalytic efficacy. Detailed studies in terms of TEM, HRTEM and XPS analysis of the hybrid copper catalyst, among others, supported its outstanding stability and reusability.
